In an age when anyone can get set on figurative fire by the Internet for one bad joke on Twitter, there’s something quaint about the continued tradition of the celebrity roast, kept alive in recent years by Comedy Central. The glaciers are melting, kids are in cages, and we all crave distraction—so here’s an evening of entertainment where Caitlyn Jenner gets the chance to tell Alec Baldwin what she really thinks of him.
The Roast of Alec Baldwin is the 17th time Comedy Central has roasted a celebrity, with past “honorees” including William Shatner, Joan Rivers, Flavor Flav, and even, in 2011, Donald Trump (his potential political aspirations did come up, which seemed a whole lot funnier at the time). Taped at the Saban Theater in Beverly Hills last Saturday, the relatively simple show brought together 10 comedians and other famous faces to sling insults at each other for several hours. It’s a concept meant to hint at danger, the chance that anyone on that stage could say something truly shocking and offensive.
The potential might be there, but it’s undermined by the fact that it’s all pre-taped—the audience, myself included, was in the rather warm theater for about three and a half hours, and the eventual special, when it airs this Sunday at 10 p.m. ET/PT, will be cut down for broadcast.
When viewers get to watch the final edit of the special, the main thing they’ll be missing is the bloopers. None of the performers had a flawless set, though their reactions to screw ups varied wildly, from Nikki Glaser’s calm request to “let me do that again” to Caroline Rhea yelling “fuck me, goddamn it!” over a blown punchline. Baldwin’s temper, referenced frequently over the course of the night, only really came out when he whiffed a few lines, saying to the teleprompter operator, “Sorry, go back, fuck suck.”
Yes, there’s a teleprompter. Yes, there are some surprises over the course of the event, including some unannounced guests, but it’s ultimately a relatively civil affair, one that’s meant to lace each barb with genuine affection for the person being roasted.
That love, though, is sometimes hard to feel. The early Friar’s Club roasts were, after all, rooted in inviting one’s friends to participate for a good-natured skewering, but one way in which Comedy Central has deviated from tradition is that each year, stunt casting tends to dominate the selection of participants.
Of the 10 people on stage, some connections to Baldwin were more obvious than others—Chris Redd, of course, worked with Baldwin on Saturday Night Live (so had Robert De Niro, but thinking about how bad he was as Robert Mueller and that he GOT AN EMMY NOMINATION FOR IT is rage stroke fuel so let’s just pretend it didn’t come up). Meanwhile, Jenner’s presence was a mystery until the reveal that she was at one point the high school track coach for Baldwin’s daughter Ireland; also, inviting her then paved the way for including Blake Griffin and thus a bunch of Kendall Jenner jokes.
Jenner is the first transgender person to participate in a Comedy Central roast, which is easy to celebrate as a real step forward for representation… though there are no shortage of jokes about her gender affirmation surgery. She wasn’t the only one whose genitalia was the source for multiple punchlines—The Hangover might have come out 10 years ago, but Ken Jeong’s full frontal scene is apparently still fair game for mockery, and roastmaster Sean Hayes introduced De Niro by noting that “his balls are nominated for a SAG Award.” But seriously, the “drink every time someone references Caitlyn Jenner cutting off her dick” drinking game will kill you. Do not play the drinking game.
Meanwhile, Adam Carolla was such a non-entity for most of the roast that while traditionally, all of the roasters begin their remarks by going around the dais and slinging a few insults at everyone present, some of them seemed to flat-out forget that he was even there. When it was finally his turn to speak, his speech did prove memorable, largely because it was an ugly, predictable rant about millennials and safe spaces, with no patience for political correctness or “cancel culture.” Yelling bon mots like “you’re all woke and no joke,” Carolla seemed more interested in roasting society than Baldwin, and it just wasn’t all that funny. Jeff Ross, who spoke after him, perhaps got the biggest audience reaction of the night by slamming Carolla’s disregard for female comedians: “Women are funny, and you should have hired some to write your jokes tonight.”
These sorts of moments so dominated the evening that Baldwin seemed to get off easy, except for one of the most brutal points of the taping—an unannounced appearance by Ireland Baldwin, who notoriously, at the age of 11, got an angry voicemail from her father calling her a “rude, thoughtless little pig.” Now 23 years old and working as a model, Ireland seemed a bit nervous on stage, but delivered several sharp remarks about Baldwin’s inattentive parenting, “joking” about him missing her birthday parties, never tucking her in at night, and the complicated custody battle that waged between him and her mother, Kim Basinger. “Mission: Impossible is what I call getting my dad to apologize” was perhaps one of her kinder moments.
For those among us with sensitive souls, participating in a roast like this might be a total nightmare. But on the red carpet, prior to the taping, Comedy Central stars including Drunk History creator Derek Waters, Corporate star Anne Dudek, and the cast of South Side all said without hesitation that they’d love the chance to be roasted some day. “If you don’t,” Waters said to Paste, “you don’t have a sense of humor about yourself—it’s scary to hear what’s true, but that’s how you become self-aware.”
From Dudek’s perspective, “it has to be done with love. With comedy, there can be this fine line where if it goes too far it’s just not funny anymore—that edge where you’re saying something really astute and really true, but you’re not getting nasty. That’s the sweet spot everyone wants to hit.”
Was there a lot of love in that room? Certainly there were sweet moments: Baldwin didn’t seem too badly bothered by Ireland’s comments, and hugged her and made room for her on the couch after she finished speaking. Every speaker ended with some kind words about the man of the night, who thanks to a matching donation from Comedy Central had used the event to raise $1 million for nonprofit organization Exploring The Arts. By the end, some truly dark moments of Baldwin’s life had become punchline fodder, but he didn’t seem too bothered. After all, it’s 2019, and the world is a hard and scary place. There are far worse things that can happen to a person than the verbal slings and arrows of the supposedly outrageous, carefully cultivated for television.
The Roast of Alec Baldwin airs Sunday, Sept. 15 at 10:00 p.m. ET/PT.
Liz Shannon Miller is a Los Angeles-based writer and editor, and has been talking about television on the Internet since the very beginnings of the Internet. She recently spent five years as TV Editor at Indiewire, and her work has also been published by
The New York Times, Vulture, Variety, the AV Club, the Hollywood Reporter, IGN, The Verge, and Thought Catalog. She is also a produced playwright, a host of podcasts, and a repository of “X-Files” trivia. Follow her on Twitter at @lizlet.