Grace O’Malley thinks the Google algorithm is f*cking with her. Because when you search her name, the person who comes up is not the 26-year-old rising comedian but an Irish pirate queen and celebrated feminist icon from the 1500s. “I usually say I hate that b*tch, but she’s actually very cool,” O’Malley says in a throaty voice that makes her sound like a Dunkin’ Donuts coffee come to life. “I’m trying to, hopefully one day, beat that pirate. But it’s hard to beat a folklore legend.”
In O’Malley’s world, she’s usually the butt of the joke. One of her most viral standup clips involves getting heckled by her own mother. During a recent appearance on Theo Von’s podcast, she described herself as accidentally celibate: “It’s funny not to be a whore but, like, really want to be.” And when we meet at a cafe near her apartment in New York City, a beverage calamity ensues. As we sit down and cheers our drinks, O’Malley’s iced s’mores mocha knocks the lid off my peppermint tea — spilling piping hot water all over me and sending O’Malley into a flurry of colorful apologies. “Am I Lindsay Lohan in Just My Luck all of a sudden?” she asks. “Did I pick up a curse or some sh*t when I was in New Orleans this weekend?”
In person, this all makes O’Malley a riotous hang — the kind of friend whose running commentary keeps you laughing even when everything’s going wrong. But on stage, O’Malley is finding lately that her self-deprecating jokes are no longer landing with her audience. “I noticed that it makes people uncomfortable,” she concedes.
Which, fair — because is there really anything to laugh at about O’Malley’s past few months? After very publicly parting ways with her childhood best friend and former Plan Bri Uncut co-host Brianna “Chickenfry” LaPaglia last fall, O’Malley has decisively won the breakup. First, she embarked on her hot-selling Down for Anything standup tour. Then came the announcement that O’Malley would be releasing her very own podcast, Disgraceful, as part of Alex Cooper’s Unwell network. (The first episode dropped today.) And for her victory lap, O’Malley and Cooper took the NFL by storm: funneling champagne bongs before a playoff game, hanging with Kylie Kelce, and hosting a special Unwell podcast live from the Super Bowl.
For a comedian who has been open about her ups and downs, including a bipolar diagnosis following a hospital stint in 2023, the internet couldn’t be more here for O’Malley’s ascent. (See: comments on her podcast announcement from “you deserve the world” to “Grace is what Unwell needed.”) But O’Malley is still struggling to take herself seriously. “The only thing I’ve ever given myself [credit for], that isn’t self-deprecating, is that I am funny,” says O’Malley, whose watery blue eyes often make it look like she’s on the verge of tears. “What I pride myself on is, in any situation, I can try to get someone to laugh. Like, when I shouldn’t make people laugh is when I really want to, because at least they forget about whatever is going on.”
O’Malley’s gruff Masshole comedic persona suggests she grew up with a pack of rowdy brothers. In reality, she has three younger sisters — Molly, Maggie, and Nora, who range in age from 11 to 23 — and was the natural ringleader. “This is so New England but my mom pinpoints [my comedy career] back to a whale watching trip,” she says. “It was the captain’s birthday and I was like 6, so I got up on a thing of stairs and made the whole boat sing to him.”
She met LaPaglia when they were both 10 years old and, at first, they did not f*ck with each other. To hear them tell it, O’Malley was “top dog” at their suburban public school and had no interest in bringing some new kid into the fold. But after LaPaglia stole away members of O’Malley’s tomboy friend group, they reached a détente on a Fourth of July camping trip and, soon after, became BFFs.
“I don’t know how to not tell the truth. That’s my biggest flaw.”
During her teen years, O’Malley’s family moved towns, forcing her to change high schools. Without LaPaglia and the gang behind her, she leaned on humor to ingratiate herself. “I tried to be the class clown the whole time and graduated with a 1.59 GPA,” she says. “I went into the guidance counselor and I was like, ‘So what colleges can I go to?’ And they were like, ‘You can either learn a trade or join the military. Those are kind of your only options.’”
After a stint in community college, O’Malley landed at the University of Massachusetts Amherst. But once LaPaglia relocated to New York to work for Barstool Sports, O’Malley eventually followed to pursue her own comedy dreams in the city. “I was working an ice cream job [in Massachusetts] and as goofy as it sounds, I had one TikTok that blew up,” she says of what inspired the move. “That gave me the boost to keep going.” (She now has over 981,000 followers on the platform.)
In the city, O’Malley spent her days working as a DoorDasher and her nights hitting open mics. She also began appearing on LaPaglia’s Plan Bri Uncut and eventually became a co-host in 2022, helping turn the podcast into Gen Z’s answer to Call Her Daddy. The pair’s breezy, longtime-bestie rapport made them highly relatable to their ever-expanding 20-something audience. Even as listeners started to suspect a rift in their friendship — around the time LaPaglia started dating country star Zach Bryan, which ended in an acrimonious split — fans still flocked to their hotly anticipated That’s My Best Friend live podcast tour last fall.
“She texted me, ‘It’s Alex Cooper from Call Her Daddy.’ I sent it to my sister. She’s like, ‘No, that’s not real. Someone’s messing with you.’”
But when O’Malley announced she was departing the podcast and “divorcing” LaPaglia last December, their relationship became a Rorschach test for those of us with complicated female friendships everywhere. I couldn’t help but project my own baggage onto O’Malley: Had they outgrown the archetypical dynamic of the conventionally attractive popular girl and her funny, actually cooler sidekick? Was LaPaglia jealous of the growing attention O’Malley was getting? Had they just been playing out the same power struggle since they were 10 years old?
“There’s a part of me that wants to talk about it. There’s a part of me that doesn’t want to talk about it [because] if I tried to keep talking about it, I’m going to put my foot in my mouth,” O’Malley says, mashing her lips together as if willing them to stay shut. “I don’t know how to not tell the truth. It’s hard to find the right words, and I always want them to be the right words. That’s my biggest flaw.”
She flails her hands and fidgets with her beanie. “I just always try to keep doing it the way I have been my whole life,” she says. “Being authentic is a huge part [of it] for me. I’m not a good liar. I did a game show with Barstool, and you can see me trying to lie on the show. I just started singing [‘When You Wish Upon a Star’], I was so nervous.”
One person she did open up to about what was happening was Alex Cooper, who knows a thing or two about public friend breakups of her own. “She texted me, ‘It’s Alex Cooper from Call Her Daddy.’ I sent it to my sister. She’s like, ‘No, that’s not real, dude. Someone’s messing with you,’” says O’Malley. “We had never met before, so it was really nice to hear from her [in that] tumultuous time. She just reached out, as a pal first. Then she asked me what my next steps were, and I wasn’t quite sure yet.” After sleeping on it, O’Malley decided joining Cooper’s network was the move. “I think it’s funny to say I’m a diversity hire because I’m not blond,” she jokes.
O’Malley then came up with Disgraceful, her foul-mouthed reimagining of old-school late-night shows, complete with a swinging ‘70s set — because every podcast now is also a YouTube show — and a slew of comedian guests including Connor Wood and Whitney Cummings, whom O’Malley opened for on tour last year and considers a mentor. “Last year, I did manifestations in my journal. Not my thing, but I heard it works. I wrote down, ‘I would like to have more money than I do in my bank account right now,’” O’Malley says. “At that time, it was a three-digit number. Looking back on just how the year has gone by, it’s just been really cool.”
To keep up with her growing career, she lives with and now employs her sister Nora as a “jack-of-all-trades” on her team. “Whether it’s my family, my friends — all my dogs eat,” O’Malley says of her it-takes-a-village approach. And that village recently turned out for seven sold-out hometown shows at Laugh Boston — a new record for that club. “It was a lot of family and friends, which was an incredible feeling. They took a limo bus and were blasting off. I was like, ‘You guys, you gotta be quiet,’” she says.
It sounds like a setup to a joke the old O’Malley would have told — a would-be triumphant moment undermined by her own rip-roaring crew. But instead, she basks in how far she’s come. “I’m not here for 15 minutes,” O’Malley says. “I’m here for 50 years, hopefully.”
Photographs by Anna Nazarova
Production: Kiara Brown and Danielle Smit
Associate Director, Photo & Bookings: Jackie Ladner
Editor in Chief: Charlotte Owen
SVP Creative: Karen Hibbert
