Solidaric Empathy and a Prison Roast with Jeff Ross
I think the reason I can get away with roasting my way through life is because it comes from a place of love.
—Jeff Ross, Jeff Ross Roasts Criminals
The lack of empathetic connection with prisoners obscures the tragedy of mass incarceration. Empathy plays a key role in our interactions with others, determining who is met with warm compassion instead of cold indifference. It shapes public opinion and policy. Yet ordinarily we find it difficult to connect with those who are dissimilar to ourselves. Further, differences in social status, as well as conflict and the stereotypes that perpetuate conflict and social stratification, block empathy, and restrict the scope of moral and political concern. Prisoners are especially dismissed through stereotypes as violent thugs, making it difficult for many people to establish any emotional connection with and concern for even the most basic prisoner rights, let alone more radical reforms. Humor, however, offers an unexpected clue as to how we might break down walls of indifference or even hostility. Humor can be used as a radical vehicle for establishing seemingly impossible connections.
Comedy Central’s “Roastmaster General,” Jeff Ross, chose Texas’s Brazos county jail and the Boston police department to bring some serious laughs and unexpected changes of heart to captive audiences both inside and outside prison walls. As the two performances—Jeff Ross Roasts Criminals (2015) and Jeff Ross Roasts Cops (2016)—continue to circulate via Comedy Central and YouTube, they illustrate the potential for media events to channel empathy across indifferent or even antagonistic audiences. To be sure, this white male comic is in many ways an imperfect vehicle for establishing an emotional bond between privileged media audiences and the incarcerated. Ross risks perpetuating the very stereotypes that need to be dismantled and yet he also puts them out there to keep it real. Through his authenticity, together with his advowedly privileged social identity and celebrity status, he is able to reach a large demographic, including those who are unlikely victims of mass incarceration and who may lack any sense of shared humanity with prisoners. The opening frame of his 2015 performance powerfully points out that there is something wrong with a system that contains more unfree black Americans than the institution of slavery did in 1850, but this history lesson is just where the comic’s work begins. The humor of someone we laugh with can bring life to simple facts and statistics. While not romanticizing the inmates at the Brazos jail, Ross’s humor performs more than a temporary break from the strictures of prison life that he claims to offer. The comic’s empathetic humor takes the form of an entertaining roast that toys with stereotypes to break through them and reach his viewing audiences.
Roasts are typically inclusive and have a celebratory tone; to roast prisoners is thus already to elevate their stature to someone you laugh with, not simply at. By seeing prisoners as worthy of a roast, Ross honors those too often viewed by his audiences as exiles, anointing them as members of the larger community. The roast is a major device for creating community through the comedic use of a type of play-fighting that carefully balances ridicule with empathy. Like bouts of play-fighting among siblings, teasing and taunting can be a form of flirtation and fun, generating camaraderie. But more than sibling teases, the empathetic humor we explore in the prisoner roast exemplifies the radical potential to cross class, race, and political boundaries. Its derisive laughter breaks down bars of separation often seen as impenetrable and resistant to ordinary forms of empathy; it creates surprising moments of intimacy even in zones of intense conflict. Unlike the ordinary use of empathy, this mix of empathy with soft ridicule offers a potential for solidarity while avoiding claims to understand those whose experiences and social position are in tension with one’s own. A willingness to play or to throw the ball with someone too often demonized and dismissed makes the roastmaster’s open-ended dialogue techniques politically worth playing with.
Setting the Stage
“Armed with nothing but [his comedic] insults,” Jeff Ross entered Cell Block 3B Maximum Security with no intent to proselytize or bring salvation, but simply to find connections wherever he could. In his gut, he must have known that he was messing with a conflict zone, tampering with multiple structures of power and animosity. When a petite prison guard named Courtney Waller reassures Ross, “You don’t have to worry—I will protect you,” he wonders how, especially given that she has no gun, or indeed a weapon of any kind. Signaling an awareness of his own privileged position, Ross, in a mock-nervous tone, jokes, “So do you just ask people politely to stop beating me?” then teasing, “If I die, it’s on you.” Waller declares, without hesitation, “We will die together,” and as Ross announces they are “blood brothers and sisters,” they pound their fists together in solidarity.
Inside the cell block, Ross finds conflicting groups of blood brothers with attitudes toward him that range from amusement to indifference. As Ross makes the rounds, shaking hands, asking “What’s up?” he crosses boundaries that seem impermeable. First, he chats with black inmates, where his nice-to-meet-you’s are followed with a sincere and yet to-the-point inquiry: “What are you in for?” One inmate explains, “I assaulted a police officer” because “they tried to take me to jail for something I didn’t do.” Ross, with a touch of warmth, adds, “You didn’t want to go,” yet the comedian cannot resist a playful tone of mockery when he rhetorically asks, “Who won that argument?”
Moments later, this self-identified Jew finds himself face to face with the “Dirty White Boys,” “a prison gang with close ties to the Aryan Brotherhood and the Nazi Low Riders.” Undeterred, Ross poignantly asks, “Who’s the baddest motherfucker?” as he approaches a bare-chested prisoner covered in muscles, swastikas, and the words “Texas Made.” “Does anyone ever get offended by your tattoos?” Ross inquires. After getting a sheepish nod, Ross wonders, “How long are you in for?” When the inmate admits he will be serving ninety-nine years, Ross, with absolute seriousness, jokes, “It should fucking be six million for every Jew that died in the Holocaust.” The inmate looks momentarily shocked and displeased, but he is quickly swept up with the raucous laughter of his prison mates, causing this baddest motherfucker with ties to the Aryan Brotherhood to humbly smile and acquiesce. A playful antagonism with his audience proliferates as Ross begins his onstage performance, taunting some volunteers waiting to be roasted by pronouncing them “the ugliest police lineup I’ve ever seen.” With a little warm-up, he singles out the infamous prison gang, inquiring, “Is this where the white dudes hang out?” As the prisoners let loose deep belly laughs, he goads “the fucking whites-only section” by wishing them a “Happy Hanukkah.” They too burst out in the kind of laughter that shakes the prison’s walls.
Humor serves as an exemplary vehicle of what we might call a solidaric mode of empathy—an empathy that can travel across conflicting social groups, as different as guards and their prisoners, or as jailed neo-Nazi gangs and Jews, to embrace viewing audiences. In laughing with others who are laughing at themselves, we find ourselves unexpectedly unlocking streams of amity for those whom we may or may not be able to identify with. While straight satire and ridicule can subvert or reinforce lines of power, empathetic humor laced with playful mockery that forces all to expose their vulnerabilities may offer more than just a momentary escape from prison life. This humor has the potential to de-escalate tensions and reveal the humanity of mortal enemies, thus opening up across social divisions a horizontal field of fellow feeling. In this volatile field, comedy and raunchy roasts may begin to redress heavy histories of social tensions. Such effervescent moments of deterred hostility transformed into shared laughter should not be dismissed as politically vacuous. The Roastmaster General reveals how laughing it up and taking one’s turn as the butt of the joke offers a compelling glimpse of fellowship, and can do so without recreating indispensable enemies. This empathetic laughter that embraces real talk offers the chance of attitudinal change right down to the viscera of the second brain. All the more in this age of mass media, when social platforms can hold anyone hostage, laughter can burst through prison walls and insulating bubbles. In much the way that an earlier era of social justice flowered with the soulful music of the 1960s and 1970s, the emotional engine of social change over the last couple of decades has grown much out of the truth tellers in stand-up comedy. Indeed, since the 1990s, and with ever greater intensity after 9/11, U.S. culture has entered an age of satire and irony, but one mixed on occasion with empathy too.
The Sympathy Revolution and Humor
Modern humor’s association with sympathy provides a backdrop for the more recent rise of empathy in stand-up comedy. The history of modern humor’s dominant strains, American intellectual and cultural historian Daniel Wickberg tells us, begins with the eighteenth century’s sympathy revolution and then changes with the rise of corporate liberalism. During the eighteenth century’s cultural revolution, an egalitarian wave of political change altered laughter’s predominant tone from ridicule and wit to a sympathetic amusement at the oddities of other people. Then in the later nineteenth century, the ground for mainstream humor shifts again with the rise of corporate culture. Corporate liberalism encouraged adaptability to the social order through the development of what has colloquially since been referred to as “having a sense of humor.” To have a sense of humor required an attitude of self-transcendence that one finds in the refusal to take oneself too seriously. The use of a corporate-friendly and politically liberal capacity for humor was thought to result in not only a more efficient workplace but also a tolerant political community by offering a sense of proportion and perspective. Thus, a good sense of humor guides the worker and citizen to transcend bothersome annoyances and avoid conflict. Wickberg further insists that the advantages of learning to work well with others applied not only to white men in professional or working-class jobs but also to ethnic minorities who, when facing prejudicial stereotypes and belittling ridicule, learn to roll with the punches and avoid conflict. No doubt, under these circumstances those who confront difficult situations rather than avoiding them could readily earn a reputation for lacking humor, and as the buzzkill or killjoy are set up for a fall.
The sympathy revolution of the bourgeois class may be traced to Adam Smith’s 1759 Theory of Moral Sentiments, but its association with laughter, albeit in a rational and orderly form, was gradual. Historians contrast bourgeois humor with an older European politics of ridicule aimed at social inferiors. Ridicule was a primary tool for the preceding age of satire from 1660 to more or less 1800. Cultural studies scholar Linda Hutcheon suggests that at that time, satire generally (though not always) functioned on the side of authority, ridiculing nonnormative behavior and reinforcing aristocratic cultures. As the story goes, these forms of ridicule gave way during the breakdown of feudalism as European elites engaged in refined games of cleverness that they called wit. In contrast to ridicule, the exercise of wit did not aim to attack or abuse others, and for this reason, its general cultivation struck many as an advance of modern egalitarian culture. Wit operates through juxtaposed ideas and images, such as wordplay based on the principle of incongruity and intellectual surprise. Nonetheless, Wickberg discerns that in exhibiting the successful practitioner’s verbal dexterity and mental superiority over their rivals, the display of dry wit declared one’s membership and status among the postfeudal intellectual elite in high society. Gradually, the egalitarian leveling of the revolutionary era weakened the presumed high status of the “useless post-feudal” class of intellects, with its air of a bygone aristocracy. The aristocratic cultures gave way to the sympathy revolution, ushering in a bourgeoisie with an alternative sensibility of cultivating not ridicule or dry wit but rather sympathetic feelings—although only those deemed appropriately rational.
Wickberg explains that by the early nineteenth century, the rising white middle class believed that the cultivation of humor deepened feelings of sympathy by perceiving other’s foibles or laughable features through their “concrete particularity.” At least in theory, it was difficult to ridicule another as inferior when one came to know them not as an abstraction or stereotype but as a “whole person,” someone with experiences and flaws much like one’s own.
In reality, there’s an undercurrent of unaddressed tensions in dominant modes of nineteenth-century humor, signaling deep problems with its alleged egalitarianism. The sympathy that may have fostered delight in the eccentricities of others among the white bourgeoisie nonetheless threatened to reduce those others to stereotypes. Think of the sympathy cultivated by Harriet Beecher Stowe toward “Uncle Tom,” the properly subservient black man in Uncle Tom’s Cabin, the novel said to have launched the Civil War. The use of such figures, even if meant to be sympathetic, perpetuates minstrel humor. Minstrel humor was not just sideshow. It was the vicious core of American humor from slavery through our new Jim Crow era, as film director Spike Lee exposes in his didactic satire, Bamboozled (2000). The dogma nonetheless prevailed that while laughter had taken delight in unexpected incongruities, now humor developed as a valued capacity for the sympathetic and yet distanced perception of oddities in other people. When we laugh at others, we see their incoherencies without resorting to demeaning ridicule.
Then, in a new twist on the modern theme, the spotlight of humor focused not on other people but on the self. Or as Wickberg elaborates, from the 1870s to the 1930s, corporate and managerial capitalism gave birth to a new type of self with the capacity to not take itself too seriously. A sense of humor came to require the sympathetic capacity to see oneself from an external point of view, and thus as an object from the perspective of others. The light of humor now shines warmly on one’s own incongruities.
Wickberg traces the development of this capacity for self-distancing to the changing world of the marketplace, where men had to learn to see themselves from the viewpoint of others and to understand the motives of an “ever-shifting terrain of strangers.” In this “constant navigating back and forth between the self as object and as subject,” laughter shifts between sympathetic humor aimed toward tolerating the other to an elevated sense of self. Of course, the modern workplace demanded the ability to adapt to a range of personalities and problems with a degree of distanced sympathy. Yet having a sense of humor primarily enhanced the ability to separate oneself from overly emotional reactions to workplace pettiness and conflict in the name of efficiency and getting along. Like an industrial work ethic, having a sense of humor, and thus a degree of detachment, would come to define the modern man. Indeed, self-transcending humor would come to serve a modern and postmodern culture “in which estrangement, standing outside of oneself, is the preferred stance,” Wickberg comments. The epitome of a refined sense of humor lies not in the hearty laugh at or even with others, but in the capacity to smile at oneself.
To be sure, transcendent humor as a type of escape and elevation could prove to be a healthy response when one is required to accept an unalterable situation. This quasi-Stoic humor of self-transcendence may well have been the quintessentially twentieth-century approach to the horrors of world wars and economic collapse, which were viewed through dark comedy as inevitable absurdities of civilization. It certainly offers a much-needed elevated stance in the face of the absurd. Yet what Freud by the 1920s had located as the reemergence of a Stoic strain of humor and Wickberg characterizes in one of its modern guises as bourgeois self-irony has its political limitations. The distancing mechanism of corporate-friendly humor, which functioned to maintain the status quo, diminishes the significant yet problematic role of sympathy for others that was prominent in humor during the earlier bourgeois era.
Although the earlier kind of sympathy may have generated a degree of social understanding and bonds of connection across society, it failed to disrupt underlying patterns of hierarchy and oppression that infected the status quo. Not only did that sympathy serve as a ready vehicle for racial or class stereotypes (“Uncle Tom”), and thus a cover for the minstrel nightmare of America; it was also gendered exclusively masculine. This gendering of sympathy not only limited its scope but also restricted its range of meaning. As Wickberg explains, true sympathy was said to demand the high-level mental capacity to take the perspective of others as well as to view how others perceive oneself in contrast to an emotion-based empathy linked with the intellectually weak. That allegedly lower type of sympathy, presumed by the Victorians to be a female virtue, was not the type of sympathy to be cultivated in the public sphere; nor was it viewed as necessitating a sense of humor. (Incidentally, the higher type is consistent with current efforts to engineer an “artificial sympathy” as part of the artificial intelligence of companion robots.) While men were said to possess the mental capacity for perceiving the perspective of the other with objectivity and thereby transcend the affects and social identities of the self, women were thought to be limited by their emotions. As Wickberg explains the alleged difference, “The sympathetic imagination allowed for intellectual breadth, an understanding of complexity, a guide to the motives of others,” not mere emotional reaction. “Sympathy allows for at least the affectation of detachment from the narrow concerns of the circumscribed self. It was this idea of sympathy, as tied to humor, that was invoked when women were said to lack a sense of humor. . . . Emotional identification that was characteristic of women’s nature, then, was not the sympathy of intellectual and perceptual self-transcendence necessary for male negotiation of the public sphere.” Wickberg also observes that as Victorian gender ideology diminished in the early twentieth century, one is less likely to hear that women lack a sense of humor. This claim does not completely fade, even if now it is more likely to have been replaced with the charge that feminists lack a sense of humor.
Yet as we know, feminists, along with other subversives, not only laugh but laugh differently. Ross’s humor joins with that of Wanda Sykes, Ali Wong, and Hannah Gadsby, stand-ups who have altered the comic stance to mix laughter with modes of empathy and a didactic intent. The trait of humor that lends a flexible sociability pacifying corporate culture can also serve a critical vibe, but only if it undergoes a bit of a transformation. Old-school renditions of this trait are rooted in a gendered legacy. Cast as a mental quality, having a sense of humor was believed to be beyond the capacities of women and other weaker minds, whose emotions and passions would blind them from taking rational aim. A detached reflection mixed with proper modes of sympathy and self-irony went along with dismissing those seemingly so caught up in their emotions they couldn’t see straight. In other words, the type of detached humor prominently hailed as important for the American democratic ethos, with its healthy business climate, can hold thoughts and actions captive, especially when it comes to those perceived as humorless social underlings, or worse yet, enemies. We understand that emotions can run too hot and can undermine human connections and conversations. At the same time, a warm sense of empathy may intimate a welcomed recognition of a distant other. Operating beyond the reason/emotion binary and its jaded gender history, Jeff Ross’s roasts, with their open-ended dialogue, serve as a fairly successful vehicle for a distinctly radical mode of empathy, one that has the potential to generate a sense of a common ground across hardened differences. Being so detached that you feel next to nothing or so emotional that you are trapped by your own biases and projections undermines the real talk and real connection that Ross pulls off in his stand-up comedy.
Yet a rational distance from the heated passions of conflict and struggle continues to appeal to philosophers and psychologists. Too often, empathy seems hopelessly saturated with emotionally based prejudices, in-group preferences, and an underbelly of hostile affects. While psychologist Paul Bloom does not examine humor, a detached stance is relevant for his defense of “rational compassion” in his popular 2016 polemic Against Empathy. “Compassion” is the term that Bloom uses to stand in for the older term, “sympathy,” in order to avoid the predominantly sad connotation that the latter’s contemporary use carries. Rational compassion strips away the emotionality that philosophers and psychologists find untrustworthy in affect-laden empathy. As we will see in the next section, philosophers have recently attempted to similarly salvage empathy by redefining it as primarily a type of perception. Yet all too often such an appeal to reason or correct perception has little political or social force, at least as a solo act.
As we know from the harrowing cries recorded in 2018 of children from inside a U.S. detention center at the Mexican border after forced separation from their migrant families, compassion for the plight of a foreigner is moved less by an abstract appeal to rights or a clear perception of harm, let alone countless pages of theory and numbing statistics, than a moment of heartfelt empathy. Despite our innate human tribalism, or rather because of the embodied social creatures that we are, feeling-oriented empathy, in contrast to modes of empathy that are primarily a form of cognition or perception, solicits the binding emotion that, together with symbolic images, energizes and inspires the commitment and action that can alter social norms. As gut-driven tribal creatures, our best hope is to break open the circle of moral concern rather than depend on some elite civilization’s ideal of reason, with its own abject underbelly, to transcend our animal nature. Humor in turn provides a vehicle for that sense of felt connection that calls on empathy as a primarily emotional rather than cognitive intelligence and a tool for social change.
Empathy via Affects and Emotions
For feminists and others viewed as incapable of self-transcendence or rational modes of sympathy, the presumed benefits of having a good sense of humor are sorely limited. Such humor does little to tamper with the structures of power. Women and oppressed groups are expected to face prejudicial stereotypes and belittling ridicule by rolling with the punches to avoid conflict.
Feminist and activist humor operates differently. As feminists along with other social critics increasingly laid claim to the public sphere through comedic interventions, empathy as a sense of felt connection with a fully engaged emotional component has worked alongside ridicule with liberatory aims. Ross’s work in the context of the anti–mass incarceration movement serves as an example of how humor can channel an engaged connection with those ordinarily outside the bounds of empathy for a potentially transformative effect. Ross stands side by side with white supremacists. He holds the hands of prisoners who have dozens of priors and who have committed violent crimes. He does not identify with neo-Nazis or murderers; nor does he stop judging them. Yet in this era of mass incarceration, there is a palpable connection with the inmates without any presumption of knowing their pain.
“Empathy is always perched precariously between gift and invasion,” writes the essayist Leslie Jamison in The Empathy Exams. There are several modes of feeling-oriented empathy. Without ever being able to explain it, we feel that the humor Ross brings to the Brazos jail is not an invasion. The question is what kind of empathy is appropriate in extreme circumstances. “I feel your pain” is a colloquial expression of an ordinary kind of emotional empathy and can serve as a fitting instance of what is called the matching theory of empathy. A matching theory, as philosopher Amy Coplan explains, defines empathy as “a complex imaginative process in which an observer simulates another person’s situated psychological states while maintaining clear self–other differentiation.” There are times when a good-willed effort to experience via the imagination another’s suffering is a fully appropriate response. Ross, however, is aware that he is free to walk out of prison while the inmates are not. He knows the privileges of his social position. Under these tense circumstances, the claim to match their pain risks theft and appropriation.
There is a second limit with the matching approach. The matching of another’s pain doesn’t work well when even the other person has little understanding of it. Consider how trauma fragments experience. Or as Jamison writes, a painful event “bleeds . . . out of wounds and across boundaries,” presenting less a buried secret to be uncovered than a murky “rhizome” of incoherent meanings. Jamison suggests that this fragmentation of experience calls for a “superlative kind of empathy.” It “requires knowing you know nothing” and “asking questions that have to be listened to”; it requires a “kind of porousness in response.” Only then can an empathetic other “deliver my feelings back to me in a form that [would be] legible.” For “feeling something was never simply a state of submission but always, also, a process of construction.” Clearly, this need to actively respond and participate in the meaning of another’s experience is more than listening alone. The other’s experience is “something actual and constructed” by both parties at once.
Yet in a situation lacking in mutual trust—where a traumatic history of race and a neoliberal calculus of winners and losers builds walls between us—even superlative empathy has trouble traveling across barriers. From a privileged position in a stratified society, the aim of delivering another’s feelings back to them (like the claim to know their pain) risks appropriating the experience of those whose suffering one may even be tacitly complicit in producing. Under regimes of racial supremacy, too many whites have found themselves unable to identify with, or even match emotions with, persons of color except through fantasies and projections. These kinds of concerns lead some feminists and critical theorists to reject empathy as a moral or political tool, leaving them struggling to find any path for the solidarity that a sense of connection can bring. A third kind of emotionally engaged empathy, or empathy as a sense of felt connection—resonating with others rather than matching or constructing their emotions—has the radical potential for generating solidarity across social divisions. We explore radical empathy as a capacity to bond where one would not expect to find it through a form of humor.
Empathy as Felt Connection
As signaled in some uses of the hip-hop lingo “I feel ya,” it may be possible to establish a tentative sense of solidarity across zones of social conflict and disconnect without invasive claims. Among urban definitions, the use we have in mind is closer to the “I hear ya” or “I’m here with you” than “I feel your pain,” but it involves from the empath a more self-aware and vulnerable stance than suggested by attentiveness alone. Consider how the laughter of the roast spreads in waves from prisoners to viewing audiences through a playful needling that turns freely on itself. A radical mode of empathy, one that moves beyond tribal loyalties, requires weakening defenses that sustain social tensions and hierarchies. This is a major function of humor. Humor breaks down defenses and serves as a catalyst for a mode of affective empathy by drawing on capacities for self-depreciation, unexpected role reversals, and a mockery that, as the Roastmaster avows in his opening remarks, comes from a place of love. Indeed, in this respect, the joker takes on the role of the mischievous eros figure from the tradition of romantic comedy. In this tradition, the eros figure is typically an enslaved person or servant concocting a plot to overcome patriarchal and other blocking forces, performing the work of intimacy and ushering in emancipatory social norms. In this case, as the empathetic humor flows beyond the prison walls, the viewing audience becomes a participant in the laughter too.
We can think of this radically empathetic humor in terms of what Bekoff describes as an egalitarian mode of social play that generates a mutual sense of connection and reciprocity. Recall our introduction’s discussion of how play can suspend social hierarchies as well as predatory instincts among carnivores and their prey to build friendships within and across species. Humor too is a form of social play with radical potential. It too can build unexpected alliances across lines of indifference or conflict. Aspects of social play that are central for humor include (1) the exposure of vulnerability and sore spots, as in self-deprecatory remarks, together with the ability to take a hit through ridicule, which is especially important for those occupying privileged positions; (2) self-handicapping or soft biting, as in the carefully gaged use of one’s wit in the soft ridicule of another, which is again important for those in privileged positions; (3) a role reversal between those of higher and lower status for mutual teasing, as who mock-attacks whom constantly changes; and (4) the right motivation fueled by the joy of camaraderie to establish the grounds for mutual trust and a level playing field. In a politically charged atmosphere, self-handicapping and exposing vulnerability allow social capital to be yielded to those occupying a weaker social position. The positive emotions of play and humor—excitement together with waves of joy in communion and mutual validation—can crack open this unlikely possibility. In short, radical empathy demands laying down privilege, and this is what humor’s promise of jovial camaraderie can achieve. The twists and turns of humor can assist a solidaric empathy by generating an unlikely zone for intimacy and emotion-laden communication without assuming that the participants are coming from the same place. The result is a tentative leveling of social divisions for felt moments that offer unexplored possibilities.
Key to this kind of humor is the willingness to take one’s turn as the butt of the joke, and thus to display vulnerability in a playful exchange of mutual teasing. Contrast empathetic humor with the scenario of joke telling that Freud proposes in his Jokes and Their Relation to the Unconscious (1905). Freud explains the pleasure of a joke through the release of energy otherwise used to repress sexual and aggressive drives. This type of joke telling turns on a fixed target of the joke and too often on gender hierarchies, thus inadvertently providing a formula for toxic masculinity: “In Freud’s account, the joke in its basic form requires three parties—two men and a woman. The first man initiates the joke to release an aggressive impulse, originally sexual, toward the woman. He forces her to participate in the joke through her embarrassment, her acknowledgment that she understands its content. . . . Through its cleverness, the joke veils and makes socially acceptable its underlying aggression. The joke does not exist until the laughter of the second man confirms it; the woman, as the joke’s passive butt, thus enables the bond between the two men.” Empathetic humor of the kind we have in mind avoids targeting an innocent object for the sake of a joke and cheap bonding. When successful, such humor has the potential for generating a vital sense of connection without relying on appropriating the feelings of others but instead resonating with them.
The capacity of a noninvasive empathy to generate a sense of felt connection is made palpable in Ross’s gestures of touch during his performance. With one hand on the shoulder of an older man, Ross explains his own identity when asked: “I’m Jewish, but don’t tell those fucking Nazis up there.” Amid a roar of laughter from the prisoners and guards, he calls out the neo-Nazi with whom he spoke earlier, urging him to take off his shirt and bare all: “Let me see those tats. Don’t be shy! Oh my god, dude. Let me tell you something. The war is over, but tattoos are permanent.”
But it is when Ross enters the women’s jail that we see how empathetic humor mixed with a poignant moment of cathartic touch offers radical play. The exchange begins when Ross finds that he is not the only comedian in the house. As he starts to warm up the crowd by setting himself up as the object of a cheesy porn, Big Mama Jo, the prison matriarch, creates ripples of laughter as she asserts her own claim to the comic stage when she shouts out, “It’s raining men, hallelujah!” Her dynamic presence encourages Ross into an open dialogue. Instinctively pushing back the invasive cameras at this crucial moment, he walks closer to Big Mama Jo as she holds out her hands in a tender moment of connection. This is not an instance where the stand-up puts a heckler back in his place to reclaim dominance of the comic stage. We sense instead a connection that is not downward-looking sympathy. It is not rational compassion and it is not matched emotion. It is an unlikely solidarity that viewers might not only feel but also share.
The connection grows with the banter between them. Big Mama Jo is surrounded by several younger women, whom Ross playfully casts as “her three illegitimate daughters.” Every bit the celebrity’s equal for laughs, this quick-witted humorist insists that what she needs is child support. To be sure, playing the dozens has a long and too easily neglected history in both black and Yiddish cultures. Trying to keep up with his rival, Ross resorts to an old schoolboy taunt about her middle-aged figure, suggesting, “You don’t need child support—how about some boob support?” Unphased by his body-shaming jives, she gives him credit for staging a comeback in this comic duel and reaches out to shake his hand to screams of laughter. When the Roastmaster starts up again—“You aren’t my mama, are you?”—without a moment’s hesitation, she snaps back, “I might be.” The threat of inmates—perceived by the viewing audience as sympathetic objects perhaps, but minstrel characters nonetheless—is real and ongoing. At times the performance falters under the weight of this threat. Yet through an unexpected exchange of wit with a prisoner able to hold her own, the audience witnesses moments when differences between two comics are leveled. Transforming mockery into flirtatious banter, we sense in them an appreciation of each other as equals.
This striking moment of unexpected chemistry between a Jewish comic, a black female prisoner, and the audience watching them makes us rethink how cognition and emotion are mixed in empathic humor. In the cultivation of empathy, both emotions and thoughts are relevant. In order to twist out of the reason/emotion and associated binaries, it is helpful to recall studies of brain dysfunction from neurologist Antonio Damasio. When parts of the orbitofrontal cortex are damaged, people lose most of their emotional capacities. In situations where ordinarily people would feel emotions, they feel nothing. One would think that these hyperrational folks would have the advantage of making decisions without subjective biases and blinding emotions. In fact, they find themselves incapable of making any significant decision whatsoever. This is because, as psychologist Jonathan Haidt explains, the decision-making capacity is not primarily a rational one but is rather visceral. Without feelings of what they like and dislike, it is difficult to make any kind of choice at all. Because empathetic humor’s connection with others is felt, not just seen or heard, it carries the spark of a socially and politically transformative eros.
Increasingly, philosophers, like psychologists, are critical of any sharp distinction between reason and emotion. Indeed, as Silvan Tomkins writes, “There is a real question whether anyone may fully grasp the nature of any object when that object has not been perceived, wished for, missed and thought about in love and hate, in excitement and in apathy, in distress and in joy.” Yet philosophical analyses of empathy reproduce tendencies from the old binary. On the one hand, analyses that rely exclusively on matching affects risk overemphasizing the capacity for sharing the same feeling—a problematic assumption in circumstances where social hierarchy persists and conflict is rife—and a more critical stance is required. On the other hand, efforts to correct this bias by treating empathy as a mode of rational thought or accurate perception of the particular other risk duplicating the problematic tendencies of nineteenth-century approaches.
Among these latter efforts, some argue that empathy relies on mental capacities to think abstractly and infer qualities present in other minds, while others focus on our capacities for the perception of others’ emotions. The former approach rests on what psychologists term theory of mind—that is, the claim that in order to understand another’s feelings, one must be able to represent them abstractly in one’s own mind. The second phenomenological approach, developed by Husserl, Edith Stein, Merleau-Ponty, and Dan Zahavi, insists that we perceive emotions directly and without inference: we see shame in a blush, joy in the tail-wag of a dog or in human laughter. Both theory of mind and phenomenological traditions emphasize a cognitive or perceptual take on empathy in contrast to an emotionally engaged and feeling-centered approach. Both traditions capture different aspects of empathy in noncontentious situations. But they do not weigh in affects and desires that constitute the core of who we are, that give texture and meaning to our reflections and perceptions, and that carry ever more significance when we occupy unequal positions and degrees of complicity in a fraught social climate. It’s these messy visceral aspects of feeling that humor productively engages for a radical mode of empathy.
The problems with the contemporary emphasis on accuracies of perceptual attentiveness or cerebral cognition (in contrast to murkier scenes of affective engagement) are easiest to see in contexts plagued by histories of trauma and social conflict. In these contexts, the demand for accurate perception or careful reflection, however valuable, risks obscuring unknowable histories of suffering beyond our ability to imagine or understand. “Empathy means acknowledging a horizon of context that extends perpetually beyond what you can see,” Jamison writes in her essay on superlative empathy. Moreover, horizons that carry histories of violence aggravated by entrenched group tensions locate us with defenses that are as difficult to bring down as they are to see through. A careful attentiveness or a cognitive-based empathy sidesteps messy affects, only to risk falling into a morass of implicit biases and intellectual blind spots. Again, the specter arises of an invasive empathy, one that inadvertently violates, instead of opening itself up to, the other.
Yet the empathy that uses humor as a soft tool of power offers a real, if humble, chance. After all, who is going to really believe an “I feel ya” from the straight man who is unwilling to reveal his own underbelly, yielding aspects of privilege and control as he lowers his defenses to laugh at himself along with unlikely others. The visceral force that Ross channels in his roasts illustrates the potential of empathy to give access to aspects of the perspectives of others as well as to poke holes in makeshift borders and unsettle set identities. Indeed, his comic routine does not end with an all-knowing smirk and shrug but with failed attempts and unexpected moments as he occasionally takes his turn as the butt of the joke. Fueled by these topsy-turvy belly laughs, empathetic humor delivers hope.
Humor enhances empathy’s transformational capacity to “feel ya,” including those whom we might otherwise easily dismiss, as it tampers with the status quo. Rather than transcending an underbelly of affects, empathy combined with humor renders us more porous and relational. Through empathetic humor, bodily openness to affects and emotions streaming from others enhances the fluidity of identity, shifting lived social positions along with the cultural landscape. Instead of fostering an attitude of adaptation that rises above a fraught situation, such humor serves as a catalyst. If self-transcendent humor culminates in, as mid-twentieth-century sociologist C. Wright Mills warns, the “cheerful robot,” empathetic humor breaks open the social circle of belonging, altering and widening the sphere of amity, and offering the potential for political realignments along with social and psychic change.
Humor has not been the only cultural force to invoke felt connections across the social landscape. Music has also been inextricably bound to a long history of struggle and liberation. Thus, against the backdrop of powerful social movements that include Black Lives Matter, Ross’s prison roast unsurprisingly pays tribute to Johnny Cash’s iconic 1968 performance in Folsom Prison. The late 1960s and early 1970s were a time when musicians and their songs captured the soul and vision of street politics. For Cash, country music was an expression of love, and his performance a mix of raw cynicism and soulful empathy. His music was such a powerful force that one former inmate recalls Cash could have set off a riot the day he played at Folsom. Cash was welcomed with open arms from a relatively homogeneous white working-class prison population whose life struggles seemed similar to each other as well as to the Man in Black. A half century later, Ross can also hear the train a comin’ as he relies on a classic Cash guitar riff and a somber glimpse of Texas train tracks to set the mood. The audiences, both free and unfree, know what side of the tracks they are on, just as they did when Cash strummed his guitar. But it is empathy tinged with biting humor, not the pathos of country music, that mediates divisive social identities, antagonistic ideologies, and territorial boundaries. To be sure, Cash did a bit of stand-up back in the day, pretending to choke on prison drinking water and purposely using foul language to mock jailhouse rules, while pointing out the injustice of doing time for petty crimes like stealing eggs. If Cash’s performances tapped into comedy, it was the music that defined much of the era. In 2015, Ross borrowed much from Cash, and now comedy has found the political spotlight.
In the counterculture of the 1960s generation, Cash was not the only example of how the power of music gives shape and momentum to our passions. Songs as diverse as the civil right’s soulful refrain “We Shall Overcome” and antiwar protestors’ bitter recognition of just who was and was not, as Creedence Clearwater Revival put it, a “Fortunate Son” recall the expansive musical range of 1960s and early 1970s social movements. We are not suggesting that music does not continue to reflect and move political thought. Hip-hop rose up in the late 1970s and for decades has provided the soundtrack to the new Jim Crow of mass criminalization and incarceration. Ava DuVarnay’s 2016 documentary 13TH narrates the roots of mass incarceration and the prison–industrial complex in slavery with rap lyrics from Public Enemy’s “Don’t Believe the Hype.” Yet in 1968 it was Cash who entertained prisoners in Folsom, and in 2015 it is a stand-up comedian who captures social media through his performances at Brazos county jail. The spotlight on prisons in 1968 was part of larger cultural revolutions across the globe, but when the Nixon administration initiated a war on drugs, something new happened. This law-and-order president targeted his internal political enemies, smearing blacks along with draft-dodging hippies as drug users. The right-wing backlash against the earlier civil rights and antiwar movements recoded his shifty politics and cynical manipulation of the race card as an attack on criminals. Demands for an end to mass incarceration, marijuana legalization campaigns, Black Lives Matter, prison-abolition movements—all provide inspiration for Ross’s prison roasts, pointing to the centrality of comedians in contemporary political thought and culture.
Such media-savvy figures as Dave Chappelle, Tina Fey, Jon Stewart, Stephen Colbert, Trevor Noah, John Oliver, Wanda Sykes, and Samantha Bee reveal that we are living in the age of the comedian. Perhaps this is why in the spring of 2016 singer-songwriter Bono insisted that the U.S. Senate “send in Amy Schumer, Chris Rock and Sacha Baron Cohen” to fight violent extremism. The laughter of stand-ups, jokesters, and satirists infuses our movements with the ripples of social challenge. These decentered currents of critique operate outside the mold of past centuries’ social movements driven by leaders and ideologies. The movements of the 1960s and 1970s, playing against the backdrop of the Cold War, were often troubled by ideological splits easily perceived through moral dichotomies—something that social media and news bubbles also engender. Yet today there are profound differences. In a decentralized social media–saturated world filled with both promise and nightmares, the comedian has found a niche, especially at a time when social change flips and flops with a notorious meme or middle-of-the-night tweet. Comic memes and tweets spreading through social media remind us of how the Internet energizes and sometimes replaces street politics. The layout of this new social media landscape seems particularly unwieldy, making elections hard to predict and social unrest hard to map out. The unpredictable shifts and restlessness of public mood reflect more than technological change. Leftist elites in the past have all too readily pinned the label of false consciousness on the “ignorant masses.” We argue that the variability in attitudes and values exposes not a false but rather a mixed consciousness. Individuals and groups have fluid identities and contradictory views. The variable flow of a mixed consciousness is too easily dismissed as a display of irrational behavior and beliefs. Yet comedy has the potential to reveal how such behavior and beliefs, no less than ideologies, are far from fixed and thus offer the possibility of felt moments of good humor between otherwise sworn enemies.
We are not necessarily looking for comedians to lead a social movement. Instead, the absence of iconic top-down leaders, foundational political ideologies, and a grand narrative style set the comic stage to address social conflict differently. Alongside such serious decentered movements as Occupy Wall Street, Black Lives Matter, and #MeToo, the comics work from experiences of pain and trauma. They expose the hypocrisy and lies of the powerful, the undeserved suffering of the oppressed, and the inequities that mark the 99 percent. And like other decentered and increasingly digitally propelled movements, the energy and power of those who can laugh forge an altered basis for solidarity from the top-down, ideologically driven movements. But if serious movements, decentered or not, mine the collective pain of victims, then solidarity for the audiences of comedy grows less from vicariously sharing the collective pain of the victims than fellow feeling among those who can laugh at themselves and with others. This laughter ensues as they confront the diversity of unjust suffering with the pleasures of an unexpected sociability. Laughter lowers defenses and crosses enemy lines because it does not rely on a common identity or collective pain to generate that wave of sociability. The suffering of Jews or black Americans may place them far afield from a neo-Nazi’s rogue life, yet in their shared humor, there is an incipient political demand.
Doing mischief in the age of misinformation, the comedian riddles mockery with the empathic humor that taps into the mix of gut emotions of post-9/11 anxiety-ridden America. The aim is not to give in to fear or to give anxiety free rein, but to redirect them to the facts. Against media bubbles and the echo chambers of friends liking friends, truth-teller comedians strip away the facade of Fox and Friends while turning fake news into real news. Increasingly, the millennials and the iGeneration find trusted sources less among the diminishing ranks of journalists than among professional jokesters. After all, Ross produces comedy as a documentary, performing the work of the investigative reporter. Like the child who exposes the emperor as having no clothes, these comedians offer what the ancient Greeks from the days of some of the first stand-ups, the Cynics, called parrhesia—the naked truth.
These comedians do more than preach to the choir. To be sure, the sharp ridicule of the Samantha Bees aims less to convince their political opponents than to energize their core. Such energizing moments can whip up enthusiastic audiences in a way that reasoned argument does not. The power to charge up an audience’s fury and disrespect against the powerful points to why authoritarian regimes for centuries have censored comedy more than tragedy. This censorship underscores the social force of comedy in that laughter may well bring down the tyrant. But if the agents of ridicule energize the base with an “us versus them” strategy, then comics who use empathy have the means to nudge us out of our respective bubbles.
Ross, for example, roasts not only prisoners but also the police, and in so doing exposes his Comedy Central audiences and YouTube fans to the hypocrisy of the criminal justice system and the humanity of those touched by it. What makes Ross’s documentary roasts such a success is more than his quick wit. The definition of who and what makes good comedy is doubtless contested terrain. Ross understands this as he reveals an assortment of comedic devices as well as other tools of the trade. However, it is his empathy that offers the kind of belly laughs that get to the guts of the matter and allows him to bridge differences and alter the collective mood. Empathy may well be why he considers himself lucky to be a comedian. In his words, “I have the best job in the world. I make fun of people for a living. And I think the reason I can get away with roasting my way through life is because it comes from a place of love.” In good humor, he adds, “I love everybody—even cops!”
Proving his love for cops, however, was not so easy. After pictures circulated of Ross at a 2016 antipolice violence rally in his New York City neighborhood, he was quickly branded as a cop hater. Only one police department in the United States would even consider letting him roast their men and women in blue. Boston police commissioner William Evans believes he runs a “compassionate department” with a clean record, and thus he wanted to “break the stereotype that we are the bad guys.” He felt that a good police roast was just what his community needed. In fact, Evans fully embraced the spotlight. “We don’t mind you making fun of us because I want the public to know that we are real people.” Nevertheless, on the morning Ross arrived in Boston, tensions were running high—not only because a police officer had been shot but also because the local police union had urged all officers to stay away from Ross. Unlike the prisoners at Brazos county jail, where they felt appreciated, even elevated, by the comedian’s attention, the Boston police felt threatened. In such a cynical milieu, roasting pigs seemed like a recipe for disaster. After all, how could you make someone laugh when they felt like a victim? Such a strong sentiment of audience mistrust and discontent was far removed from loyal customers’ frequenting their favorite comedy club.
While Ross understood that going to a prison or a precinct would not be like his previous comedy tours, he did not consider himself to be anticop. With both compassion and a determination to not let anyone off the hook, Ross struggled with a charged political atmosphere that makes even questions and inquiry seem suspect. At an antipolice rally, Ross was visibly moved by the protesters who took to the streets in an attempt to bring an end to the growing list of unarmed black Americans that had been shot by police or died while in custody—so many names, Ross tragically pointed out, that reading them all would take all day. One protester after another tells Ross about a lost loved one gunned down by police. A grieving mother of a slain eight-year-old girl confesses to the camera, “My anger keeps me going.” Another woman, Madge Morgan, is haunted by the past and present. “I was nine years old during the 1967 riots and [sic] white national guard pointed bayonet rifles at me and my baby brother and sister’s head . . . and told us ‘you little nappy-headed niggers get your asses back in that house before I blow your heads off.’” Upset and yelling, she passionately admits, “I want people hurt.” This is where Ross’s empathic touch comes into play amid a roller-coaster ride of emotions. Not wanting violence ever, Ross asks Morgan, “Can I have a hug?” as he jokes about how he “cops a feel.” This skillful move instantaneously turns Morgan’s anger and Ross’s ambivalence into laughter. Feeling reassured, Morgan asks Ross if he thinks blacks and whites are equal. He replies with affirmation as he mischievously adds a reminder of another contemporary out-group: “Of course, Mexicans are better than all of us.” Taking down pieces of a wall rather than building one, the rejoinder causes both of them to laugh more as they hug each other tighter.
For Ross, empathy is not simply a performance but a gut instinct that makes it impossible to separate the terrifying violence suffered in black communities through police action from unfair blanket hatred and targeted attacks on the police. In New York, at the antipolice violence rally, surrounded by the “families of the victims . . . it’s like a funeral. A big angry funeral,” insists Ross, who is almost at a loss for words when he meets armed protesters ready to shoot. Violence begets violence. As angry protesters shout threats in the face of police positioned to protect their lives and keep the peace, Ross becomes overwhelmed: “This is intense, weird and disturbing.” It is an all too familiar political conflict; everyone wants to know “what side you are on,” assuming that if you are not for one cause, you are against it. Meanwhile, Ross concludes, “People are dying on both sides and nobody is talking to one another.”
Just as the names and statistics of black victims haunt Ross and his performance, so too do the occupational stresses, strains, and violence faced by police. The often poorly paid job of the cops, we learn from Ross, leaves them with a 70 percent greater chance of heart attacks than other Americans. On a ride-along, Ross brings his audience out of their social bubble as he documents what it feels like to put on a bulletproof vest as part of a daily routine. Recall, a cop had just been shot when Ross arrived in Boston; luckily, not only did he survive, but the assailant was restrained without gunfire. There is little sympathy for the police, and they know it. The police joke about being hated except for that brief moment after the 2013 Boston Marathon bombing, when “everybody else runs away, you run in.”
For Ross, wondering just how he can build up trust across what feels like an impenetrable blue line is not easy. As he was told by one of the officers, “Part of a cop’s nature is to be cynical . . . it takes a while to feel you out,” which is why this same man in blue suggested to Ross if you want them to trust you, start by “buy[ing] them lunch!” After all, “the way to a cop’s heart is through his stomach.” Getting to the guts of felt mistrust demanded not only that Ross bring pizza to the officers but also a round of belly laughs. Along with handshakes, fist bumps, and humorous jibes, a once chilling if not hostile reception transformed into a comedy club atmosphere. After some warm-up acts and ride-alongs, Ross gains the trust he needs to address the issues at hand. Without hesitation, Ross tells his police audience, “I have a theory why cops love donuts so much—because they look like they’ve been shot.” Continuing on his comedic course, he treats the crowd to more raunch, joking, “I beat my penis so much I call it Rodney King. And just like the LAPD, I always get off.” Like Ross, his audience understands that there is a kind of natural propensity to laugh deep to handle hard times. After all, as one cop told Ross after listening to a desperate man who needed help from nonexistent social services, “You got to laugh at this shit or you cry.” Yet Ross is not providing laughs simply for their immediate relief. He is creating moments that humanize those who are demonized without losing a critical stance toward police-based terror and the new Jim Crow. While highlighting the problems of police brutality, he nonetheless is able to transform anger and mistrust into a laughter that ripples across divisions that were once thought to be impenetrable.
Bottom-up Humorists Steal the Scene on the Streets of Boston
Out of the precinct and on the streets, empathetic humor opens ever more doors for rehumanizing the other, and with them, ourselves. With Bobby and Brian, two of Boston’s finest, Ross finds himself in an impromptu exchange of jokes and real talk between the white cops and a group of black friends nonchalantly hanging out in front of a storefront sign that warns: “No Loitering, Police Enforced.” As Ross and the police officers approach the group armed with jokes, not threats, the camera captures how the affect of the comic stage takes a life of its own. Laughing with not against the white cops, the black men loitering on the sidewalk are happy to be on camera as long as they don’t have to “stop smoking [their] weed.” Amid the joviality, a young man toys with the irony of his ankle monitor, and thus a previous far-from-pleasurable encounter with the law. Unwittingly, the ankle monitor nicely sets up Ross, who scores another round of laughs when he all too innocently asks, “Does this mean you can’t go near a schoolyard?” Ross then jokes with someone whom he dubs Spike Lee, a young black man with a San Antonio Spurs cap and vintage glasses who insists that “this is real talk—cops killing black people,” yet who also implies something more nuanced: “It’s not [always] like that. They’re doing their job. You feel me.” But, he adds, “Fuck the fake ones. The real ones they don’t come out here for violence.” As real talk slips back into jokes and jibes, Ross’s open-ended technique reveals he is not the only roastmaster on the streets that night; his newfound friends mock him for humor they consider so old school that he must be “Jerry Lewis.” With a grin, he takes his turn as the butt of the joke, yielding for series of moments to their scene-stealing wit, showing us viewers how it’s done.
There are occasions when this street comedy and camaraderie tragically threaten to turn on out-groups. Ross, for example, is taunted for wearing a winter coat with fur that looks like “Chinese pubic hair,” and as everyone laughs, we are reminded once again of the long-standing need for an indispensable enemy. Ross and his street friends seem to find nothing off limits, yet this take-no-prisoners approach to a roast is deeply entrenched in an empathy that challenges the solidification of the other as enemy. “Hating all cops for what some cops have done, that is also prejudice,” insists Ross. He gestures toward another layer of racial anxiety when he explains, “It’s like hating all Mexican people because you got diarrhea from a chimichanga.” As Ross feigns a meal gone wrong, he groans, “Fuck the Mexicans . . . I’m voting for Trump,” reminding us just how easy it is to find an outsider to blame, and how easy it is to build walls rather than breaking them down.
Who would have thought that a roast in situations as raw as the line that divides cops and blacks on the street would provide the way open toward a more generous and truthful life? Yet in the wake of the war on drugs and other backlashes against the freedoms that defined the 1960s and 1970s, laughter offers a chance to connect with others in a world rent by struggle and strife. Music has long been a means to find that bond with others, mixing strong empathic impulses with symbols of unity and a desire for social and political change. Since 9/11, these impulses and symbols of longing for change have found their way through comic truth tellers as real talk elsewhere has become hard to find. The cathartic propensity to laugh from the gut to handle hard times takes out chunks of a wall rather than building one when empathy transforms the anger and mistrust that fester across histories of crimes not easy to forget or forgive on both sides of the line. Ridicule turns into a free-for-all and defenses weaken as a bottom-up roast offers a chance for each side, if only they can open themselves enough to take their turn as the butt of the joke. Recall that empathy together with reciprocity ground our animal sense of fair play—and so too our golden rules for both ethics and comedy. With no one fixed as the permanent enemy, each side exposes its vulnerability to the biting humor of the other in a gesture of friendship and camaraderie as old and as common as the play among carnivores and those who would have been their prey. “Can you feel me?” does not demand that either side relinquish its judgment of the other or fail to acknowledge the real crime of white supremacy in America. On the contrary, the roastmaster mixes with his humor lessons in history. Yet comic play introduces into ridicule a solidaric empathy that can penetrate impenetrable boundaries, rehabilitating not only the criminal but also humanity itself.