Mike Sweeney doesn’t do lawyer jokes. Even when he was practicing law by day and doing stand-up by night, he didn’t do lawyer jokes. His reluctance was fueled by a sense of mortification at his chosen profession. “I was kind of ashamed of being a lawyer,” he says.
Not so of being a comedian. Sweeney NCAS’79 is proud to say he’s spent the last three decades making people laugh, first as a stand-up comedian and then as a comedy writer for Bill Maher and Conan O’Brien. Sweeney liberated himself from practicing law in the late 1980s, back in the day when you could afford to live in New York City on $100 a week. He spent nine years making the rounds of New York’s comedy clubs, often doing six shows a night, seven days a week. About a schedule that the less amusing (or energetic) among us might consider grueling, Sweeney says, apparently without irony, “It was fun.”
It was also excellent timing. The city’s comedy scene was catching fire, and it wasn’t unusual for Sweeney to share the bill with up-and-comers like Colin Quinn, Chris Rock, Jon Stewart, Joy Behar, Adam Sandler, and Sarah Silverman. He’d typically rise at 1 p.m., prep for his comedy set around 8, then head out to a diner with his fellow comics at 3 a.m. to rehash the night’s work.
Family life, in the form of a wife and a child (eventually two children), nudged him into the less (but only slightly less) fraught gig of comedy writing. For one season, starting in 1993, he was a writer on Politically Incorrect with Bill Maher. In 1995 he applied for a writing position on Late Night with Conan O’Brien—his third try—and got the job. He kept it for the next quarter century, becoming, in 2000, head writer of the show—and its later incarnations as The Tonight Show and Conan.
“It’s kind of been like getting on a speeding train,” he says. Initially, he was intimidated by the experience of sitting in a room with nine other writers pitching jokes out loud. Once he realized he’d have to sink or pitch, though, he adapted, and, before long, he was loving the job in all its chaotic intensity.
He also loved working with O’Brien, who became a close friend. Sweeney remembers how much his boss loved dropping into the writer’s room, where he’d often launch into an impromptu performance. Like O’Brien, Sweeney now loves an audience of writers. “You wanted the studio audience to like what you’d written,” he says. “But you also wanted Conan and the other writers to like it.”
There were certainly days when that didn’t happen, though they were far outweighed by the good days and his two Emmy wins. That was a good thing because comedy writing for a nightly show incorporating topical humor is very close to all-consuming, with workdays often extending past midnight. After a nine- to 12-week run, he’d get a week off, during which, Sweeney says, “I was a dishrag.”
Sweeney says his experience at Rutgers University–Newark, where he majored in history and minored in English and music, helped prepare him for a life in comedy. “A liberal arts education and having a lot of odd jobs are very helpful,” he says. (Before becoming a lawyer/comic, Sweeney was a lifeguard, a deli guy at the A&P, and a mailman.) Comedy writing, he explains, requires an ability to “pull references out of the air—and if you have a well-rounded education, that helps.”
His time at Rutgers also informed his decision to become involved with Rutgers Future Scholars, which puts first-generation, low-income, academically promising middle school students on a path to higher education. It offers full scholarships to students who complete the program and enroll at Rutgers. Sweeney and his wife, Cynthia D’Aprix Sweeney, are avid backers and in 2020 created the D’Aprix Sweeney Family Rutgers Future Scholars Endowed Fund to support the program.
“I loved going to Rutgers in Newark,” Sweeney says, “and so I was very drawn to a program that seeks out and works with young local students in the hope that they’ll one day attend this great college in their backyard.” Sweeney has also participated in several virtual town halls for the program.
Now, Sweeney is cohosting Inside Conan: An Important Hollywood Podcast with fellow Conan alumnus Jessie Gaskell. It’s a wildly free-form exploration of O’Brien and his shows, past and present. And O’Brien has tapped him to write and produce a new show that’s in the works.
Sweeney’s still feeling the buzz from his long association with the show. “When things went well,” he says, “it was incredibly rewarding—and that feeling never went away. Twenty-five years has literally rocketed by.”