Live From The Alec Baldwin Roast: Insult Comedy In The Era Of Cancel Culture Anxiety

I didn’t read the talent list before I accepted a press invite to Comedy Central’s Roast of Alec Baldwin, and it turned out that was probably a good thing. I might not have accepted if I’d known that the list of luminaries lighting up the dais would include: Blake Griffin, Ken Jeong, Caitlyn Jenner, Caroline Rhea, Nikki Glaser, Jeff Ross, Chris Redd, Adam Carolla, and Robert DeNiro. It was like an AI-generated list of comedic low-hanging fruit.

An hour of Caitlyn Jenner jokes? Honestly, it didn’t sound all that enticing. But it did raise an interesting question: in an era when comedy is so often a front in the culture wars — the weeks before the taping saw the release of Dave Chappelle and Bill Burr specials promising to offend and trigger us, and the week after gave us the Shane Gillis kerfuffle — where does an ancient tradition of “edgy” humor like the celebrity roast fit in? Is a format predicated on ironic invective and Borshty one-liners still relevant, or is it the rhinestone-encrusted death rattle of a once relevant artform?

It was a long evening, largely funny though occasionally not, and I came away oddly heartened. I came away thinking maybe, just maybe, it’s not comedy itself that’s gone out of style. Maybe it’s the idea of comedy as something cool, or the idea of comedy as brave, raw, unfiltered truth-telling that’s getting old. The roast was devoid of any pretense of biting satire or truth-to-power and strips comedy down to its basest form — a cheesy lounge act, a kind of magic show. And maybe… it’s better that way?

There was a time in my life when stand-up comedy meant a lot to me. I devoured every joke book I could get my hands on when I was a kid and I had an encyclopedic brain for them. Blonde jokes, Polish jokes, dead baby jokes, the interrupting cow — I loved them all. I didn’t know what a “Polack” even was or the societal implications of being blonde, but I loved the structure. A condensed story with a twist ending.

Later in life, I forcefully loaned out Chris Rock and Patton Oswalt and Mitch Hedberg specials to friends and love interests as if they were the Rosetta Stones of my personality. I even went on to perform comedy myself for a good 10 years, though almost never in the obsessive, hitting-three-open-mics-per-night way that becoming a touring comic requires (partly because I was never 100% sure I wanted to be a touring stand up. Success in that line of work seems to mean not dying in a hotel room).

These days stand-up comedy just… doesn’t mean that much to me. I don’t know if I was just too close to it for too long — seeing your friends do the same-ish 10 minutes 200 or so times will certainly sour you on some aspects of it. That feeling of comedy’s creeping irrelevance: personal issue or larger societal trend? I go back and forth, but it feels like somewhere along the line we put comedians onto this pedestal as “brave truth-tellers.” We started dissecting and quote-tweeting their material as if truth-telling was the aim all along. It felt like a misread of the comedic act in the first place. Comics who once benefited from this perception — Chappelle, Louis CK — now rebel against it.

These days we’re oversaturated with stand-up comedy and when a special actually does manage to cut through the noise, it’s almost always in political terms. Just the other day, rightwing milk boy Ben Shapiro called Bill Burr’s new special “shocking and audacious. “The wokescolds will be out in force on this one,” he tweeted, with the kind of call-to-action typical of today’s comedy recommendations. Oh no, I have to watch this special so that the wokescolds won’t win!

Dave Chappelle’s latest special is another cultural battleground, one I haven’t brought myself to watch yet. I keep hearing what liking it or not liking it will say about me. One acquaintance said it was funny but that the “gay zealots” might not like it. What if I laugh!? What if I don’t laugh!? The stakes are too high.

If we weren’t defending Chappelle and Bill Burr from the wokescolds, we were buying tickets to Booksmart or the new Ghostbusters or Hannah Gadsby so that the misogynists don’t win. Isn’t it all a bit exhausting? Maybe there’s no perfect world where the act of laughing is perfectly apolitical, but could it at least not be so performative? Laughing because you think you should is by far the least satisfying kind of laugh.

Here’s a summary of my night at the Alec Baldwin roast.

Opening Act

Watching on a TV screen from inside the press lounge at the Saban Theater in LA (a spread full of miniature food, including sliders, mini-hot dogs, and mac and cheese cubes, plus a full bar of which I plan to partake enough to justify the Lyft ride), comedian Pete Lee warms up the crowd. He’s not part of the official show, just a kind of warm-up comic who gets to do a short set and tell the crowd how to behave so they don’t fuck this whole thing up. He’s kind of like the comedy version of the graphic at the beginning of the movie that tells you not to talk or text — necessary social engineering.

Lee points out that everyone on the dais has been paid to be there and that they don’t need your sympathy, and that you’re not going to be their savior for booing someone’s mean joke about them a year from now. This is actually solid advice for anyone, not just roast attendees. All fans of Disney/Apple/Johnny Depp/Michael Jackson should hear it.

“Pretend it’s 2014, okay? Take a vacation from being triggered,” he jokes, which will become a theme for the evening. “This is a safe space for being offensive.”

The Roastmaster

Next on the stage is the roastmaster, Sean Hayes. That’s right, the guy from Will & Grace (arguably its biggest star, the one who played the character who wasn’t Will or Grace). It’s hard to tell if this collection of people is just a Surreal Life-esque attempt to create the randomest collection of people possible, for spectacle/comedy purposes, or if these are all just people with shows to promote in the Viacom family of brands. I’m guessing it’s a little bit of the latter using the former as a cover.

Hayes, though a fairly random choice on paper, makes a good emcee. He opens by telling us that we’re gathered here tonight to roast a huge dick (Baldwin). “Can someone remind Ken Jeong what a huge dick is?” (Ken’s small dick was a running joke on The Hangover movies).Ken Jeong laughs way too hard at the first zing, which will also become a theme.

Hayes’s job is an important one. By virtue of being the first, he sets the de facto parameters for the kinds of jokes that are acceptable at the roast. Despite the opening speech about boundary-pushing and no one getting offended, it’s not as if there aren’t any boundaries. If someone came up and shouted the N-word for five minutes they’d probably get tackled by security. The “insults” still have to be structured like jokes.

Trans people are clearly the newest frontier in roast humor. They’re the one group represented here (in the form of Caitlyn Jenner) not to appear in those “Tasteless Jokes” books all of the comics in attendance probably flipped through as kids. Thus, there’s less historical precedent for acceptable ways to joke about trans people (even in the context of an avowedly “triggering” spectacle). It’s unspoken, but everyone’s sort of wondering what the first Caitlyn Jenner joke will be.

“Don’t worry about bombing, Caitlyn. Anything you don’t like can be cut,” Hayes says.

And we’re off. It’s a simple, elegant, wordplay joke that gets everyone onboard. Hayes didn’t necessarily have to joke about Caitlyn Jenner’s transness, specifically — Jenner is also a trans Republican, a father and stepfather to America’s most obnoxiously ubiquitous reality TV family, and someone who escaped charges in a vehicular manslaughter case — lots of material there. But Hayes has established that it’s all fair game and done it pretty non-hatefully.

Nikki Glaser

Nikki Glaser, a 30-something comedian whose thin, platinum blonde looks will inspire multiple insulting comparisons to Anne Coulter later in the evening, is up next. One of her first jokes, “the only difference between me and Caroline Rhea is opposite eating disorders,” falls a little flat.

It might seem odd that a fat joke would get more scrutiny than a trans joke or a small dick joke, but I think it’s less offensive than momentary confusion (which can always kill a laugh). Caroline Rhea, who’s more like a slightly plump aunt, doesn’t immediately read as “fat.” At its best, humor is self-policing like that. If a joke is too mean or not quite accurate enough, it just doesn’t get laughs (assuming the audience isn’t terrible, which can be a big assumption).

Glaser quickly brings everyone back and ends up having probably the best set of the night. She goes after Caitlyn Jenner for being a bad father to his first family and for voting Trump. “What does that party have to do to lose your support, be your son?”

She refers to Alec Baldwin as “Justin Bieber’s wife’s oldest, fattest uncle” and tells Robert DeNiro, “I’m so honored to share a stage with you. And by stage I mean the final one of your life.”

For some reason I enjoy the death jokes best of all. Sean Hayes had a great one about how Alec Baldwin had four children with his much-younger yoga instructor second wife so that he’d have “young, strong pallbearers.”

It’s around this point that I realize, to my surprise, that I’m having the best time I’ve had at a comedy show in years.

Ken Jeong

Ken Jeong goes next, and mostly succeeds in proving that roasts aren’t really his best format. He might just be too ingratiating (as evidenced by laughing way too hard at everything) and also too hammy, so that he tends to break character before he’s finished delivering the joke. He punctuates every one-liner with “Now…” like he’s pausing for laughter before moving on. Only there isn’t enough laughter. So now it just seems like a weird tic with the curtain pulled away.

Chris Redd

Chris Redd, who’s been on Saturday Night Live since 2017, is up next. He was the only roaster I didn’t know and most of the jokes at his expense are about people not knowing who he is. He keeps flubbing lines and having to re-read them (something you don’t see at normal comedy shows but that happens at live roast tapings). His best jokes are often about himself messing up the joke. Though at one point he refers to Alec Baldwin as an “Emmy-winning, bread-faced river pig.”

I don’t really know what it means but I love it. Another of Redd’s weird jokes is about black folks having a soft spot for Alec Baldwin because “he has the same eye color and temperament as every pit bull we’ve had to put down.”

There are times a weird premise beats a great punchline.

Lady Gaga, Caitlyn Jenner, Caroline Rhea

Lady Gaga appears via video message, thanking Alec Baldwin for supporting Tony Bennett’s charity for supporting arts education in schools. Gaga wisely doesn’t attempt jokes but “here’s Lady Gaga on behalf of Tony Bennett” is already great as conceptual humor.

Caitlyn Jenner does a mostly forgettable set where she congratulates herself for having the guts to be onstage (sure?) and for spawning and/or raising so many rich and famous kids (yeah hey no thanks). She does a joke about Caroline Rhea eating a pastrami sandwich on the toilet that falls flat and refers to Jeff Ross as “Jeff Rose.” She can’t seem to breathe out of her nose.

Caroline Rhea, best known as the aunt on Sabrina The Teenage Witch (underrated show, IMO), has been a comedian since the eighties and it shows. She has one of the best sets of the night and by far the best Adam Carolla jab, of which there were disappointingly few: “What can you say about Adam Carolla that he won’t tell you himself in one of his insufferable tirades that he’s trapped you in?”

Blake Griffin

The former LA Clipper/current Detroit Piston proves surprisingly capable, at first a little sheepish about the brutal set he has to read but the laughs give him confidence and he ends up delivering one of the most flub-free, well-timed sets of the evening. Note to Judd Apatow: no, this is not an invitation to give Blake Griffin a role in a rom-com. But Griffin was a confident reader and whoever wrote his jokes did a sharp, unsparing job. (To DeNiro) “Do we really need you to die before we see you in something with a decent plot?”

Adam Carolla

If Adam Carolla, moderately well-known conservative, isn’t an outlier in this group (and in general Hollywood is far more conservative than they like to pretend) he seems dead set on convincing everyone that he is. It’s like he can sense the audience’s uncertainty towards him and decides to push them away before they can reject him. The set is like a 10-minute defense mechanism.

Carolla opens thanking Sean Hayes for “reminding us of a bygone era when gays had a sense of humor,” which, like the Rhea fat joke, is such a wild stretch (gays are all humorless now?) that it’s confusing enough not to get a laugh. It’s the kind of whiff the teller would love to blame on “outrage” but mostly no one’s outraged we’re just kind of like “huh?”

It mostly goes downhill from there. Carolla does a riff on acting being the only profession where “blowing a fat Jew” is the only barrier to entry (a Harvey Weinstein reference). There’s actually a decent joke about actors in there, like it requires no expertise and anyone can do it (if you squint really hard?), but after the opening gay joke, all anyone can hear is how hard he hit the J in “Fat Jew.”

Carolla does get in one good Epstein joke — “What do you miss more, Alec, the plane or the island?” — but he’s essentially begged the audience to hate him and they’ve complied (Ken Jeong is still laughing though). Carolla essentially stops doing jokes completely towards the end and goes on a rant about “social justice warriors” who have “already ruined the Oscars” (excuse me, when were the Oscars ever good and/or not a notoriously thin-skinned audience?). He hits “safe spaces,” “cancel culture” — basically every square in Fox News culture war bingo (incidentally, one of Carolla’s most recent projects was a documentary called ‘No Safe Spaces,’ co-produced with right-wing grifter Dennis Prager). Carolla flips off the audience with both hands on the way out.

It’s a thoroughly disappointing performance, especially for me, a person who fell asleep to Carolla’s voice on Loveline virtually every night in high school and college. Carolla was an integral part of my upbringing, telling us it was okay to masturbate and preaching a crotchety kind of acceptance in his nasally whine (which, believe it or not, was actually kind of groundbreaking to those of us listening from religious small towns). He got increasingly crotchety over the years, the targets of his rants shifting from the religious to taxes to Mexicans, and I gave him the benefit of the doubt for years, but at some point he crossed a rubicon.

I’ve seen so many of my friends’ fathers turn into Fox News Dads with insufferable politics over the years, and always felt blessed that it never happened to me. As I watched him bomb while speaking a patois only other Fox News Dads and Stormfront Uncles could understand, I began to realize that Adam Carolla has become the Fox News Dad I never had. He’s that once-beloved relative I watched slide slowly into bigoted incomprehensibility until he was eventually too far gone to bother with.

Robert De Niro

There are a few more sets — a long one from perennial roastmaster Jeff Ross, with lots of jokes to choose from in the edit, and surprise appearances from Triumph the Insult Comic Dog and Alec Baldwin and Kim Basinger’s extremely tall daughter, Ireland — she of “rude little pig” voicemail fame. Ireland gets in a series of solid digs, including “Mission Impossible is what I call trying to get my father to apologize.”

Alec’s reactions are jokey but seem genuinely pained. In general, Alec Baldwin seems to have the perfect reaction face for every joke. Whatever you think of him (I can’t watch his awful Trump impression and he seems like he’d be a huge asshole in private but I otherwise love him as an actor), Alec Baldwin is a savant both at acting and at being a celebrity in general, and it’s even more impressive to watch it live.

Finally, Robert De Niro takes the podium. He ends up being a sort of lower-energy, Hollywood liberal version of Carolla, speaking in his own, weird, unfunny vernacular where Will & Grace is “The Lindsay Graham of sitcoms,” Baldwin’s awful Trump impression is genuinely a threat to the White House, and Robert Mueller is still the avatar of the #Resistance as if the last six months never happened (De Niro compares Baldwin to Mueller as a compliment). Maybe method actors just aren’t built to read dick jokes off a teleprompter?

The Baldwin Rebuttal

Baldwin goes last, naturally, getting in some solid jokes in some unexpected directions. “Blake, I wish we were as close as your eyes are,” he tells Blake Griffin. He jokes that Carolla’s podcast is “number two in the mass shooter demo.”

In a final moment of surreality, Baldwin introduces Paul Anka. Anka, a very small man whose face is an absurd shade of burnt orange and sort of looks like one of the shrunken head people from Beetlejuice, sings Baldwin off to a rendition of “My Way” as the crowd files out and the credits roll. Everyone has had juuust enough alcohol at this point not to react to this like a bad acid trip.

And just like that, the evening was over. No one cried, no one got booed off stage, and no one was canceled. Some of the jokes were bad, but most of them were funny, and when a joke wasn’t funny, one had simply to wait for the next one.

Are roasts weird anachronisms? Absolutely, and that may be their best quality. All the jokes were variations on the same series of joke formats — wordplay, misdirect, pun, “I don’t wanna say___, but ____!” It exposed comedy for what it really is — a kind of low-stakes sleight of hand, a loungey magic act made of words. In a weird way, the unabashed dopeyness of it all reminded me what I liked about comedy in the first place.

Best of all, I almost never had to think about a comedian’s “brand” or what laughing at one of their jokes might mean for my brand. After it was over I didn’t think people needed to know that roasts are killing humanity or that they had to watch this roast for the good of the republic.

The whole thing was refreshingly unimportant. For one night comedy didn’t feel like it had to shoulder the weight of all of our cultural ills. Maybe that’s when it’s easiest to laugh at.

Vince Mancini is on Twitter. You can access his archive of reviews here.