Chelsea Handler’s New Stand-up Special Is the Epitome of Wine Mom Comedy

Chelsea Handler opens her new special, The Feeling, by thanking the “homosexual” fans who’ve gotten her where she is today — particularly the gay men, whom she gives a special shout-out for their part in having gotten vaccinated against monkeypox a few years ago so that straight people “never had to deal with” an epidemic. Handler goes on to share useful public health information about how the disease is spread: anal penetration is the main one, so the CDC said you should “avoid” it, “as if it just sneaks up on you at the bank,” Handler jokes. But she also lets straight audience members know that anal penetration is “trending,” and advises anyone thinking of trying it out for the first time, “You have to pick a medium to small male. Can’t do that with 50 Cent. No. Jo Koy, maybe, but not 50 Cent.” 

That’s the thing about a Chelsea Handler special: When you fire it up, you can’t say you don’t know what you’re going to get.

Handler is approaching the end of her third decade as a stand-up comic. She’s also hosted her own talk shows, produced other people’s talk shows, written books, raised money for Democratic candidates and been feted for her allyship to the LGBTQ+ community. That “allyship” has sometimes been undermined by jokes suggesting that publicly homophobic politicians are actually queer and closeted. Handler has also faced controversies about her fetishization of Black men, her confused attitudes about white privilege and her support of Israel. Not to be reductive, but: yes, all of that does describe a typical white liberal woman in her 50s.

Handler may not have unlearned all her worst tendencies and ideas, but based on The Feeling — which dropped on Netflix today — she seems to have mostly learned which ones she shouldn’t talk about on stage. A few iffy jokes barely qualify as acceptable, like the one about 50 Cent and Jo Koy. Making it specifically about two men Handler dated (including one who made his penis size a matter of public discussion himself) as opposed to a racial generalization of the kind she might have made 10 years ago: that’s growth, of a sort. Then there’s the story about a classmate named Aaron who was permitted to mutter profanities in the schoolyard because, as a teacher explained, he had Tourette syndrome — which, once a young Chelsea looked it up, she decided she had too so that she could curse out her dad at the dinner table. A joke about this disability was edited out of The Simpsons decades ago, but Handler cannily frames hers as kid nonsense; the butt of the joke isn’t Aaron, it’s the father Handler didn’t respect — and, secondarily, Handler herself.

“Kid nonsense” is a good shorthand for the first half of The Feeling, which paints a clear picture of what young Chelsea was like. She claims her contempt for her parents began at birth, when she saw they had brought her, as the youngest child of six, into a family that afforded her no chance of upward mobility. She became fixated on making money, which she did easily by opening a hard lemonade stand (“to parents and anyone over 10 — obviously, I had guidelines”) and babysitting, saving close to $8,000 as a pre-teen; a formative motivator was taking her first-ever plane ride at age 10 and feeling she was meant to be in first class, which her mother couldn’t afford. The triumph she describes at taking a flight the next year with the first-class ticket she secretly booked and paid for herself — and sending her twentysomething brothers to the back of the plane without her — is entirely unsurprising given the woman Handler has become.

When she wasn’t trying to make money, young Chelsea’s main activity seems to have been sexual self-gratification. This is something, we hear, that she discovered by chance one summer at the family’s vacation home in Martha’s Vineyard (“I know that makes us sound like we were wealthy. We weren’t. I don’t know how my dad got that house. I’m sure he stole it from somebody”) when a cast on her broken arm bumped up intriguingly against what she calls her “Pikachu.” All her friends back home seem to have also just learned about this pastime judging by her invitation to a sleepover expressly built around getting “the feeling.” As a performer, Handler can seem armored, so the extensive excavation of her younger self’s often humiliating sexual adventuring gives her an unexpected vulnerability; it also makes a great case for why Handler doesn’t want a daughter for herself who might be like herself.

Talking about recent events in her adulthood gets Handler into material that’s a lot more expected, and a lot less winning. First, there’s the story of the first COVID summer she spent, with her siblings, in a rented mansion in Maine. When one of Handler’s sisters warns her that it’s in a right-wing area, Handler intensely describes how excited she was about “disrupting a Republican enclave”: “I’ll have sex with all my Black friends and Asian friends, we’ll do anal on the lawn all day long, saluting your fucking flag!” It turns out Handler is friends with the Bush twins, Jenna and Barbara, the latter of whom invites Handler and her siblings to Kennebunkport for pickleball. (Handler and I don’t agree about everything, but we’re in lockstep on having heard everything about that sport that we’ll ever need to.) Handler doesn’t want to go and risk running into her friends’ father, former President George W. Bush, and making a scene. But her siblings talk her into going: She just has to get very high first. 

At the compound, even though Barbara had promised Handler that “Daddy” wouldn’t be there, he is; he wants a hug; he wants to show Handler his paintings; and, at her request, he takes a selfie with her. And… that’s it. Handler has told this story many times prior to its appearance in the special, saying he was a “nice guy.” I know a certain kind of liberal has decided that any Republican who can manage to behave with more decorum than Donald Trump is respectable. But, again, Handler is someone who’s received multiple accolades for her support of the queer community, so she probably doesn’t agree with him that queer couples should be barred from being foster parents, that “Don’t Ask, Don’t Tell” was “a good policy” or that a constitutional amendment should have banned same-sex marriage. (We know for sure she doesn’t agree with him on Texas’s anti-gay sodomy law, which he “strongly supported” as governor until it was struck down in 2000.) I guess Handler thinks repeated mentions of the four edibles she took for this visit make her seem edgier and the story less shameful than Ellen DeGeneres’s defense of her friendship with Bush back in 2019. I can’t say I agree.

The best proof that Handler thinks Bush’s reputation has been laundered is that her name-dropping story about him comes without caveats. That’s not the case with her chunk on her early COVID crush on Andrew Cuomo, though it goes on for so long I wasn’t sure if she just hadn’t heard that he’s become radioactive since then. (She has.) She’s also got a story about meeting Bill Cosby before his scandals had come to light; I won’t spoil the kicker, but it does close the special on an ugly, sour note she apparently thinks is cheekier than I do. 

The early going of The Feeling tells us Chelsea Handler has always been herself; maybe the end tells us she always will be. If you feel like hearing from a wine mom type and the ones in your actual life have already told you all their stories, The Feeling might give you exactly the feeling you’re looking for.