On a recent night at a renovated warehouse in Brooklyn, the comedian Alison Leiby stood in front of a crowd that included her parents and cousin, her publicist and some of her closest friends and favorite comics, and opened with a joke about her vagina.
She got a shocked laugh, then drew an even bigger reaction when she acknowledged how awkward it was.
“We’re starting there,” she said defiantly. “We don’t need to ramp up to that.”
During her 12-minute set, Leiby described the weird feeling of being topless while wearing jeans and shoes during a mammogram, which she called a “reverse Winnie-the-Pooh situation,” and skewered cultural assumptions about what men and women read. “There’s only two genres of books being marketed to women right now,” she said: romance novels about fairies and centaurs having sex and books about how “a rich lady is getting a divorce.” Books for men either have ponderous titles like, “The Boat That Won the War,” or consist of “a transcript of a crypto podcast,” she added.
She closed with some of her riskiest material — riskier even, in her mind, than her jokes about getting an abortion: her gleeful assertion that she never wants to have children.
“People say things to you if you’re a woman who doesn’t want kids,” she told the crowd. “Sometimes people will be like, ‘Oh, so you hate kids?’ and it’s like, yeah.” She waited a beat. “I do.”
The punchline drew a mix of scattered applause and stunned laughter, but Leiby undercut the tension with a deft follow-up — chiding people who insist that she’ll never understand love until she has a child.
“OK, you haven’t seen my cat,” she said. “I want to put his whole head in my mouth.”
The performance kicked off a comedy show to celebrate Leiby’s new book, “I’m a Lot.” In funny, intimate essays, Leiby reflects on everything from her shopping and reality TV addictions and the shocking things her Barbie dolls did to one another, to her near-death experience at 19 from a blood clot after surgery and her struggles with chronic back pain and opioid dependence. She also writes about why she doesn’t feel bad for not feeling bad about having had an abortion, and why she refuses to feel guilty for not wanting children.
The stories share many of Leiby’s signature moves from her stand-up: a willingness to be sincere and vulnerable without getting sentimental, goofy anecdotes that sneak in sharp cultural observations about gender, and a highbrow-lowbrow blend of jokes that make fun of serious things and rants that take trivial things extremely seriously.
A self-described “chronic overachiever,” Leiby, 42, has been working nonstop as a comedian for 15 years. She made her mark in television, churning out political satire for topical late-night shows, writing for “The Marvelous Mrs. Maisel” and punching up jokes for the comedy series “Broad City.” But the medium where she feels the most like herself is stand-up.
“She’s a beast, she could just write joke after joke after joke,” said the comedian Ilana Glazer, who recalled seeing Leiby onstage and being blown away by her caustic bit about a women’s magazine article that recommended drinking a glass of water — as a snack.
“She’s always looking out for: What are the most absurd things about walking around as a woman in this world that is systematically traumatizing us daily?” Glazer said, noting that Leiby makes the trauma funny. “And it’s a relief.”
A lot of Leiby’s comedy career has involved figuring out how to be funny when it’s hard to be funny. In 2022, she performed an acclaimed one-woman show about a decidedly unfunny subject: having an abortion at a moment when women across the country were losing access to it.
The show was a high-wire act of poking fun at a sensitive, even painful topic. But abortion isn’t the most divisive issue Leiby broaches.
At a time when comedy has become more welcoming to women than it was when Leiby started out, it’s her material about vehemently not wanting kids that can still feel like something of a no-fly zone. Women in comedy have broken taboos when it comes to talking about drugs, sex and their bodies. Prominent female comics, including Ali Wong and Whitney Cummings, have done screamingly funny standup about the indignities of pregnancy and child-rearing. But a woman proudly proclaiming that she doesn’t want children still manages to rankle.
“It just shocks me how it’s arguably a more prickly subject than abortion,” Leiby told me.
With “I’m a Lot,” Leiby wades into the subject in a more sustained and serious way, though she still jokes about the absurd expectations women face, as they’re pressured to either be hot, skinny and single or become mothers (and then, ideally hot, skinny mothers).
In a chapter titled, “I’m Child-Free,” she describes how women without children are often objects of disdain or envy, or sometimes misplaced pity from people who view life without children as the greatest tragedy to befall a woman.
Leiby has experienced the full suite of reactions, from strangers and even acquaintances. “While I fully expect the culture to label me as someone to pity or envy or hate (or all at once!), it’s not something I expected real people in my life to do,” she writes. “Yet it happens all the time.” She finds the infighting among women particularly depressing.
“We’ve got to stop pitting mothers and nonmothers against each other,” she said. “The enemy is men.”
I met Leiby on a sweltering summer day at her apartment in the Gowanus section of Brooklyn, where she’s lived for eight years. As we chatted over cans of mini Diet Coke, we were occasionally interrupted by her 18-pound tuxedo cat, Rizz, who rolled around on the carpet, flailing on his back like a beached whale and meowing insistently.
“Meow meow meow,” Leiby replied to Rizz’s theatrics, a phrase she also uses in standup as filler, like “yadda yadda.”
“Want to go do your screams?” she asked him. Rizz sometimes stares at himself in the bathroom mirror and screams, a habit he picked up from her, she joked.
Leiby started doing stand-up at 26, when she took a comedy class at the Peoples Improv Theater. She was in agony from a herniated disk and sometimes deliriously high on painkillers, but was instantly hooked on the adrenaline jolt she got from trying to make an audience laugh.
While still recovering from her third back surgery, she started going to open mics every night. Over time, Leiby’s sets got sharper. She appeared on lineups with comedians like Zach Galifianakis and Janeane Garofalo, and ran successful shows at Upright Citizens Brigade, a Manhattan comedy mecca. She was often broke, stealing toilet paper from bars, bumming tampons off friends with office jobs and living on hummus, but she’d never been happier.
After years of trying and failing to get hired writing for late night, Leiby finally landed her first TV job in 2016. It was a dream gig: writing edgy jokes for Triumph the Insult Comic Dog, a foul-mouthed hand puppet voiced by the comedian Robert Smigel, who frequently showed up on “Late Night With Conan O’Brien” and other late-night shows.
“I was like, I found my voice,” Leiby said. “It’s a mean dog who smokes a cigar.”
In her mid 30s, Leiby had a stable job, with a steady paycheck and health insurance, writing for “The Marvelous Mrs. Maisel,” a hit show about a New York woman trying to make it in comedy. But she felt oddly unfulfilled. Her most high-profile work, the jokes that commanded the biggest audiences, had all involved writing for other characters.
In standup, Leiby had always talked about her life. So after she had an abortion at age 35, she started telling jokes about it.
A staunch liberal and supporter of reproductive rights, Leiby was not ambivalent about ending an unwanted pregnancy. She believed women should be able to think and talk about abortion not as a life-defining tragedy or an invitation to judgment, but as something “annoying and tedious.”
She turned that material into “Oh God, A Show About Abortion,” which opened Off Broadway in May 2022, just days after news broke about the Supreme Court’s leaked opinion overturning Roe v. Wade. There would no longer be a constitutional right to abortion, and every night Leiby was asking people to laugh with her about hers.
The response was overwhelmingly positive, but Leiby was also distraught that the buzz over how necessary the show felt was tied to the end of Roe v. Wade.
“I had waited so long in my career to have something that was mine,” she said. “And then I did, and it’s attached to this really dark thing.”
To Leiby, the show was both a career-defining moment, and a bitter disappointment. When the show wasn’t picked up as a comedy special by any streaming platforms, Leiby was devastated it wouldn’t reach a bigger audience.
“It was a huge success, and it ended in failure,” she said.
After the show closed, Leiby struggled to figure out what she wanted to say and how to say it. She liked the freedom of long-form narrative, and wanted a project she could control. So she started writing essays about parts of her life that didn’t fit neatly into a setup-punchline format.
The night of her book party, Leiby huddled in the dressing room of the Bell House with four comedian friends — Josh Gondelman, Liza Treyger, Claire Parker and Ashley Hamilton — who had joined the evening’s lineup to kick off her reading and book signing. Leiby sipped a beer and looked at her phone and went over her set list, a seemingly incoherent string of words in a small Moleskin notebook: “books for women & men.” “42 mammograms.” “almost died.” “child free.”
Leiby’s friends congratulated her on having her book plugged on a sidewalk chalk board in front of Canal Bar, her favorite Gowanus dive bar.
“The marquee!” Hamilton said.
“I’m literally a celebrity,” Leiby replied.
Onstage later, Leiby, who had projected confidence all night, admitted she felt nervous about people reading parts of the book that expose her complicated, broken friendships and failed relationships.
Then again, her exes would likely never pick up the book, she reasoned, delivering a final, irresistible jab.
“There’s a whole chapter about men,” she said. “But none of them read.”
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