How Louis C.K. Became the Darkest, Funniest Comedian in America

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A few days later, C.K. opens the door to his Manhattan apartment and, padding around in black athletic socks, leads me to his living room. The vibe is cozily cluttered. Antique rugs cover wood floors. There's a fireplace with an amp and a karaoke machine nestled into it. A portrait of Miles Davis hangs on one wall, and there's a trumpet on the mantle – C.K. loves jazz – beside several pictures. In one, he and his girls, Mary Lou, six, and Kitty, nine, mug goofily. (C.K. and his ex-wife, a painter he doesn't care to discuss, share custody.) In person, C.K. is friendly without being particularly warm: happy to answer questions lengthily, uninterested in small talk. He sits down behind a massive wooden desk with a vintage typewriter on it, gesturing for me to sit on a nearby couch.

He doesn't want me to identify his neighborhood. Boundaries are important to him. When he receives gifts from fans at shows he doesn't open them. If they salute him on the street, he politely keeps moving. When you tell jokes as soul-scouring as his, people can mistake that onstage candor for real-world intimacy. "I've had people bump into me outside my building, accidentally-on-purpose," he says. "I don't want some guy to John Lennon me."

C.K. tries not to be rude, because he knows what comedy fandom feels like firsthand. As a kid he'd play and replay stand-up LPs by Bill Cosby and Steve Martin, feeling a connection to them, loving the casually gripping way they spoke. "I remember watching this Robin Williams special in the Seventies," C.K. recalls. "He poured insane energy into the show, and at the end, the camera followed him backstage, and he sat down on a couch looking deeply distressed. Reeling. He wasn't like, 'I did it!' It was him, alone. I thought about it a lot. I was like, 'A really tired guy who's working hard? I could be that.'"

He was raised in Mexico City, where he lived until he was seven, at which point his family moved to Massachusetts. C.K. was a depressive kid. In junior high he took to drugs, "closing myself off from feelings," he says. "Eighth and ninth grade were two solid years of dropping acid, snorting coke when somebody had it, Quaaludes, an alarming amount of pot, mescaline, drinking. By the time I got to high school, I was a recovered drug addict." C.K. ran for a time with a bad crowd, breaking into cars and snatching valuables within. (These days he drinks minimally, and the only time he gets high, he likes to joke, is when he hurts his back and gets to take Percocet.)

Money was tight. His dad, a Hungarian-Mexican economist, moved out when C.K. was 10. His mother raised him and his three sisters herself with a paycheck she earned as a computer programmer. (When I ask C.K. if his dad is part of his life today, he replies, "Not so much," and changes the subject.) Living "near the highway" in the Boston suburb of Newton, C.K. cleaned pools, fixed cars and spent a year as a Kentucky Fried Chicken cook; he brought home KFC turkey dinners two Thanksgivings in a row. After that, he clerked at a video store, where he discovered hardcore porn. "I remember one called Personal Touch III," he says. "It was a subjective-camera porn, where they talk to the camera as if it was you. At the start, each cast member introduced themselves, so it's this girl: 'Hey, I can't wait to have this time with you.' Then another girl. Then this fucking guy goes, 'Hey, I'm Steve Powers, and I'm going to be getting all this pussy while you're playing with your little fucking dick, you loser!'" In C.K.'s comedy, lust and self-laceration are intertwined, and no wonder: Even his porn called him a loser.

Despite a C average in high school, C.K. impressed an NYU-admissions interviewer, who told him the film school would accept him if he applied. C.K. blew it off. "I just couldn't fill out the paperwork. Getting my old transcripts and putting a stamp on an envelope? It made me want to vomit," he says. "I'm still like that. That's why I have an assistant."

One night, he heard a radio ad promoting an open-mic night at the Boston comedy club Stitches. "I was electrified," he says. Amateurs were offered five minutes; C.K. prepared in earnest – and bombed. "I did less than two minutes and walked off to pure silence," he recalls. "It was a total failure. It was terrifying and uncomfortable."

He was hooked. Working hard, he built a reputation, his sense of humor tending toward the absurd – you can watch him on YouTube telling a joke in 1987 in high-pitched dolphin-speak. "He was admired and respected early on," recalls the comedian Greg Fitzsimmons, who came up in Boston around the same time. "His material was conceptual, and he was loud. Boston crowds had this aggressive attitude. The way Louis dealt with it was by taking them off-kilter and jarring the audience."

When C.K. moved to New York around 1989, a stand-up hotshot on the make, he'd race his Honda Super Sport 750 motorcycle up and down the FDR Drive, doing 100 mph between gigs, his pockets bulging with cash from promoters. "I had the world by the fucking balls," he recalls. Then things came toppling down: He crashed the motorcycle, banging up his body. The Eighties comedy bubble burst, clubs closed and ticket sales waned citywide. Stand-up gigs were increasingly hard to come by. He once drove all the way to Norton, Virginia, and Chillicothe, Ohio, "holding down the fort at a Holiday Inn lounge for these drunks and making, like, $150." A New York-area promoter shorted him brazenly. "What are you going to do about it?" the guy asked; hard up, C.K. worked with him several times afterward.

In 1993, he got a call he describes as life-saving from a former SNL writer named Robert Smigel: Would he like a job on a new show called Late Night With Conan O'Brien? "Louis' stand-up was too interesting to ignore," says Smigel. C.K. joined the writing staff, earning $2,500 a week and opening his first-ever bank account.

C.K. was a major force behind Late Night's early, unhinged laughs: He'd dress up as an ant and interrupt Conan's interviews, or re-enact Apocalypse Now with pieces of fruit. As a stand-up with a strong independent streak, C.K. enjoyed the collaborative energy of a writers' room, but made sure to carve out his own autonomous turf. "Robert let me do anything I wanted," he recalls. "I got to shoot some elaborate, crazy shit there." Smigel says that C.K. would bridle at the job every now and then, but the rebellions took mirthful form. "In the writers' room, Louis found the most creative ways to waste time. Once, he started throwing money out the window with notes attached to it, like, 'You pathetic pig.' People on Sixth Avenue would pick up the money and read these vile notes, and he'd be looking down, laughing."

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