The 36-Year-Old Virgin

If you're one of the many who paid to see the $150 million–earning Knocked Up last summer, then Craig Robinson's face should trigger a laugh or three. In his first mainstream film role, he made an impression as a nightclub bouncer denying entry to the pregnant heroine (Katherine Heigl) and her 40-plus-year-old sister (Apatow's wife, Leslie Mann). Largely improvised, the scene is Robinson at his best, equal parts scolding and sweet as he tells Mann, "It's not that you're not hot. I would love to tap that ass. I would tear that ass up. But I can't let you in 'cause you old as fuck—for this club, not, you know, for the Earth.”

Now, a year later, Robinson is starring in Pineapple Express, the latest Apatow outing for which the producer has teamed up with Knocked Up's Seth Rogen. Needless to say, he's thrilled. "It's like being a role-player on a championship team's bench,” he says. "Come in, shoot a three, then go back to flirting with the cheerleaders. But now I'm trying to become a starter.”

His early days are the stuff of Apatow's films, in fact—full of dead-end jobs, rejection and girl trouble. After graduating in 1994 from Illinois State University, the Chicagoan followed in his mother's footsteps, working as an elementary school music teacher by day. But by night, he'd work the mics as a struggling stand-up comic. One particularly unforgiving gig was at a place known as Heckler's Heaven—a Chicago bar that regularly held open-mic nights and was known for its make-or-break audiences. There, if your joke bombed, you'd be assaulted by a cavalcade of rubber chickens, culminating in an offstage yanking à la Sandman Simms. "Man, did I suck the first time I played there,” says Robinson. "With all the boos, you'd have thought it was bin Laden onstage.”

Undeterred, he decided to cull from his own experiences: embarrassing, relatable and hilarious anecdotes from his college days, delivered with a twist. "I figured I'd at least be original,” he says. So he took the stage armed with funny real-life stories and his Roland JV-30 keyboard. "One night when I was in college, I [booty-called some girl and] started singing a Craig Robinson original: ‘Can I Have Some Booty?'” he says. Although amused, shorty wasn't buying it. "She was laughing, but more at me than with me,” he recalls. Still, he thought: What made one girl giggle could surely make a crowd cheer, right?

Robinson took that logic all the way back to Heckler's Heaven. And then one night, sitting behind his instrument, switching from spoken-word to singsong, he suddenly didn't suck. "The crowd was hypnotized,” he says. "I've never done a stand-up set without that keyboard since. It's crazy what not scoring some booty can do for a brother.”

In the realm of up-and-coming black comedians, Robinson is a fresh voice. Rather than shocking and awing like Dave Chappelle, or tapping into our sociopolitical subconscious like Chris Rock, Robinson takes on the everyday—guys-versus-girls issues—with a subdued, sardonic approach. "I sincerely believe in the hope that there's somebody out there for everybody,” he deadpans. "And the more I date, the more I realize that my person died at birth or something.” His punch lines are delivered with the same matter-of-factness as their setups, leaving audiences simultaneously disarmed and intrigued. "He's this big guy with a sweet, teddy-bear quality,” says Judd Apatow. "He can get away with being vicious because you're always sensing the nice sweetheart behind it.”