In 1997, Garry Shandling’s meta-sitcom, The Larry Sanders Show, aired an episode chronicling the behind-the-scenes preparations for a roast of the eponymous fictional late-night host. Though the event promises to celebrate Larry, it ends up being a disaster. Jerry Seinfeld drops out at the last minute. Bill Maher mainly performs jokes from his own act. Dana Carvey and Bruno Kirby use the stage to bicker with each other. Meanwhile, Larry quietly stews over barbs about his vanity and perceived homosexuality—mostly delivered by people he doesn’t respect, who appeared only because they were cajoled or pressured.“This is the worst fucking night of my life,” Larry eventually remarks, not long before before the prop comic Carrot Top, the evening’s surprise guest, takes the stage to skewer him. Although Larry’s publicist insists that the roast is a Hollywood rite of passage, the episode humorously illustrates how the industry has sapped all of the romance out of the showbiz tradition. Instead of being a raucous tribute to a friend, it’s become something akin to a networking event, another venue to cultivate notoriety.I thought about this episode while watching Netflix’s The Roast of Kevin Hart, in which multiple comedians and celebrities gathered to poke fun at the actor-comedian. This was no Hollywood rite of passage, but a humiliation ritual posing as a party. At Hart’s roast, no insult was off the table: height jokes, one-liners about Hart’s phoned-in movies, jabs at Hart’s father’s crack addiction, references to Hart’s frequent co-star the Rock that sometimes doubled as references to Hart’s father’s crack addiction, smirking nods to Hart’s many product endorsements, and even more height jokes. Unlike Larry, Hart seemed to take the canned insults in stride by hamming up his feigned outrage and ostensibly genuine laughter for nearly three hours. But to me, the environment felt artificially joyous, and cemented how the roast has evolved from a venue for comedic expression into an opportunity for sanctioned cruelty, all in the name of admiration. The first-ever roasts were closed-door toasts to theatrical luminaries, such as Oscar Hammerstein, by members of the private New York Friars Club in the early 1900s. It was only in 1968, nearly 20 years after the Friars Club started hosting annual member roasts, that one was televised, on Kraft Music Hall, an umbrella title for several musical variety series that aired on NBC. In 1973, Dean Martin borrowed the format for the final season of his self-titled variety show in an attempt to boost its flagging ratings. It ended up being a huge success. A subsequent series of specials branded as The Dean Martin Celebrity Roasts aired for a decade and featured mid-century A- and B-listers—many of whom were good friends or had been working together for years—cracking wise about famous roastees, such as Frank Sinatra and Mr. T.In 1998, Comedy Central began producing and televising the traditional Friars Club roasts. A few years later, the network launched its own line of specials, which took inspiration from the Friars Club and Dean Martin ceremonies but also courted controversy by embracing a raunchy one-upmanship sensibility. Though a veneer of good-natured joshing persisted, a coarser approach defined by “Roastmaster General” Jeff Ross, a frequent writer of and participant at those roasts, replaced the kinetic playfulness from the Dean Martin days. On a recent episode of Dana Carvey and David Spade’s podcast, Fly on the Wall, both veteran comics pointed to the 2002 Chevy Chase roast as the moment when the format jumped from fun to foul. “I could tell there was pain in his eyes,” Carvey said. “I thought, Is this like an execution or something?” (In that same episode, Carvey announced that he has agreed to be roasted at a future date.)After falling off the air for a few years, the tradition was revived for 2024’s The Roast of Tom Brady, Netflix’s first-ever live roast special, featuring Brady, the former Patriots quarterback. A hit for the streamer, the roast was viewed more than 2 million times on its debut night, and featured Brady taking cracks about his divorce and the New England Patriots’ cheating scandals on the chin. (His good-sport facade faltered only once, after Ross made a crack about the prostitution scandal involving the Patriots’ owner, Robert Kraft; Brady went over to Ross and appeared to admonish him.) The special was a relative commercial success partly because of its choice of victim. Brady, a pro-athlete sacred cow beloved by fans and hated by rivals, was a prime target for teammates and comedians alike, who all relished taking him down a peg.Early in the Hart special, Brady himself appeared onstage to snark: “I guess it wouldn’t be a Kevin Hart project if it wasn’t a shitty sequel.” To the credit of whoever wrote that joke for Brady, The Roast of Kevin Hart was indeed bloated and repetitive. Throughout the night, every roaster doubled down on variations of the same obvious observations. (Because of the way roasts work today, Hart wasn’t the sole target of the evening’s gibes: Lizzo is fat; Pete Davidson has a dad who died on 9/11; Sheryl Underwood is Black and had a husband who killed himself.) Callouts regarding political allegiances and dubious sexual histories were deployed—often in rigid, clumsy ways.Roast material tends to be circumscribed by a limited range of preapproved topics. Any “shocking” jokes have been carefully choreographed to inspire gasps from the crowd while flattering the unflappability of the roastee. Hart may not have known that Shane Gillis, the night’s host, would say that he could be lynched only from a Bonsai tree. But despite the racist overtones, the statement was within the range of what was acceptable—it, too, was ultimately just a height joke.Early on in the special, Ted Sarandos, Netflix’s co-CEO, could be seen grinning in the audience. His presence was a clear symbol of brand support for Hart, who has been in the streamer’s fold for years, and most recently hosted the Netflix comedy-competition series Funny AF. “I did say that Kevin was a Hollywood puppet,” Katt Williams, a longtime critic of Hart’s, remarked onstage. “I meant that the head of Netflix literally has his whole hand up Kevin’s ass and can make him do anything.”[Read: Stand-up comedy, all joking aside]Of course, Netflix has also produced four of Williams’s stand-up specials since 2018, and many of the other guests also regularly feature on the streamer’s programming. Following Williams’s logic, Sarandos could make most everyone on the dais do just about anything. The overwhelming Netflix presence at The Roast of Kevin Hart, combined with a grin-and-bear-it vibe from the participants, made it feel less like a comedy show and more like a branding event.That calculated atmosphere became downright phony whenever the comics acted like deploying slurs or racist and misogynistic jokes was an act of bravery. “Freedom of speech is alive today,” Underwood announced during her routine, as she publicly thanked Netflix and Hart for showing “that we can all come together and crack jokes on each other and still respect each other.” But any respect for Hart exhibited by the performers was partly downwind from the money and attention they received by appearing onstage. A longtime roast attendee, Hart knows that there’s plenty of profit in performing a loud, rude style of stand-up at the expense of craft or taste. Whether she intended to or not, Underwood said the quiet part aloud when she praised Hart by saying he was a “great businessman and a great performer”—in that order.Ironically, one of the most memorable roast moments in the tradition’s history came from a subversion of these faux-cruel expectations. At Bob Saget’s roast in 2008, Norm Macdonald was instructed by the show’s producer to be as shocking as possible. Instead of skewering his friend, however, Macdonald delivered antiquated material modified from a book of corny one-liners. “I don’t know how to insult people and call them names and stuff,” Macdonald later said of his routine. “Because I would feel really bad, because everything you say, it has to be true, you know, or it doesn’t make any sense.” Nasty words tend to blend together, but unique points of view stand the test of time.