By Nash Jenkins
November 25, 2015

It was the Saturday after Memorial Day, and the comedian John Mulaney—perhaps the funniest man to ever spend a night with Bill Clinton—had come home to Chicago to reminisce about it with a few thousand of his former neighbors.

“I’d learned to play his campaign song on the piano. It was ‘Don’t Stop’ by Fleetwood Mac, from Rumours—an album written by and for people cheating on each other,” he said. “He let us know who he was right away.”

Never mind that there were those in his audience at the Chicago Theatre who were maybe too young to listen to Fleetwood Mac, or to remember Clinton’s first presidential campaign, or to get Mulaney’s digressions into the plot of The Fugitive. Mulaney, 33, was only ten on Election Day ’92 (and, as he’ll be the first to remind you, he looks like he still might be), but he has a knack for bringing the crowd in on the joke. His 2012 standup special New in Town, which brought him to the vanguard of a new generation of comedic talent when Netflix began streaming it early last year, showcased his schtick: astute riffs on the quiet, usually dark absurdities that lie within everyday things—Law and Order: SVU, commercial airplane travel, the New York Post—delivered with a self-conscious boyishness.

These days, though, the joke is often himself. His newest special, which was filmed during his Chicago Theatre performance and went live exclusively on Netflix this month, is an hour-long symphony of chipper self-scrutiny: “the adventures of this one idiot,” as he describes it to me, “who has high self-esteem for some reason—despite a lot of missteps.” Even the Clinton story is as much about Mulaney and his family as it is about the Clinton himself (Mulaney’s parents, Chip and Ellen, overlapped with the 42nd president at Georgetown and then Yale Law School).

“No one had your specific family, and your specific life. You can always draw from that,” he says of his shift to the personal. “Because no one’s gonna go, ‘Hey, I have a story about your dad.’”

He tells me this from his home in California, where he lives with his wife, Annamarie, whom he married last July, and Petunia, their French bulldog, who sleeps in a patch of sunlight on the floor while we talk. (“She likes California,” he says. “She likes windows.”) This is the fodder of much of his new routine, which mostly materialized within the last year. He’s been touring endlessly—usually selling out auditoriums—which he describes as a long trial-and-error session for the standup special.

“Most of the things that stayed are stories that for some reason I genuinely feel passionately about every time I’m standing up onstage,” Mulaney says. “Even the most trivial, stupid things—like, for months, I’ve looked in the mirror and said ‘I still feel this way about HGTV.’”

The Comeback Kid, the title of Mulaney’s new special, refers to Clinton’s self-appointed media nickname from the 1992 campaign; it does not, Mulaney says, refer to himself, though those acquainted with the last thirteen months of his life may be tempted to infer otherwise. After seizing popular attention with his standup, Mulaney created, co-wrote and starred in an underwhelming eponymous sitcom, which premiered last October to a deluge of unflattering Seinfeld comparisons. It was canceled within half a year.

But to call Mulaney a comeback kid logically implies that he went somewhere, probably somewhere pretty lousy, before coming back. But that sitcom is just one entry on a precociously long résumé. He’s first and foremost a standup comic who came of age on the eastern seaboard: first at Georgetown University, where he did improv with comedians Mike Birbiglia and future collaborator Nick Kroll, of Kroll Show; then in New York, where at twenty he spent a summer doing open mic shows at night, interning at Comedy Central by day (“copying tapes and delivering envelopes,” as he remembers it, fondly), and sleeping on Kroll’s couch.

Even if you’re unacquainted with Mulaney’s standup, there’s a good chance that he’s made you laugh before. The Saturday Night Live character Stefon, Bill Hader’s strung-out Weekend Update city correspondent, was created by Hader and Mulaney together; his Weekend Update debut in November 2008 came less than three months into Mulaney’s tenure on the SNL writing team.

You’ll see one facet of Mulaney’s comedic worldview in Stefon, who calls to mind the campy, ketamine-fueled club kids of Reagan-era Manhattan nightlife. Nostalgia inflects some of Mulaney’s strongest material; he’s good at locating the minor stereotypes that color a certain ethos. Mulaney and Kroll are currently getting ready for an off-Broadway stint as their Kroll Show characters George St. Geegland and Gil Faizon, two aging Upper West Side nudniks whom it’s easy to imagine hanging out at the YMCA while copies of the New Yorker from 1991 yellow on their coffee tables.

And yet there’s something modern about his schtick, too. Mulaney douses the grim with prepubescent charm, distorting the lines between the ironic and the sincere; in turn, he proves that maybe that line never really existed. His self-effacement persists offstage too. When asked to put into words the philosophy that runs through his comedy, his answer is straightforward.

“Oh, aren’t terrible things great?” he says. “And isn’t it funny when things go wrong?”

Contact us at editors@time.com.

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