Derrick “Capone” Lee adopted the Gangster of Comedy moniker when he started doing stand-up. (Apollo Theater)

Sitting in a prison cell at the age of 25, Derrick “Capone” Lee had a lot of time to think.

The man now known as the Gangster of Comedy — who has shared stages with Tracy Morgan and Shaquille O’Neal and hosted weekly shows at the Apollo Theater — had spent the previous eight years selling drugs in the Bronx, where he was born and raised.

But sometime during his nine-month sentence, Lee realized that “three hots and a cot” was not a future he could deal with. Lee’s life needed a rebranding.

“Prison was definitely something that I needed at that time,” Lee says. “Drug dealing was never a thing that I wanted to do — it was almost something I got into because everybody else was doing it. I knew that jail wasn’t the place I wanted to spend the rest of my life, so it was given up right there.”

(Lee’s camp wouldn’t release details of his sentence or his age.)

For his first job out of prison, Lee served as a home attendant for the mentally disabled, trading the street corners where he used to conduct business for living rooms.

He knew he liked helping people, especially through laughter. But it wasn’t until some prodding by the regulars at the barbershop where he also worked that he considered trying comedy for real.

“It definitely wasn’t something where I said, ‘Hey, I’m gonna be a comedian,’ ” Lee says. “Everybody was like, ‘You gotta give that a shot.’ ”

Lee discovered he was a natural with a mic in his hand. In the years since he made his comedy debut in a 1992 amateur contest at Columbia University, he’s made his mark as host of the legendary Amateur Night at Harlem’s famed Apollo and with appearances on HBO’s “Def Comedy Jam.”

Unflinchingly real and unabashedly provocative, Lee is not one to avoid controversial topics onstage. Race, gender, sex, religion — name a touchy subject, Lee is going there. Always the business type, Lee realized early on that he needed a brand to stand out in New York’s hyper-competitive comedy scene. Thus was born Capone, the Gangster of Comedy.

The name Capone was given to him during his days on the street, Lee says, as a nod to the similarities between his demeanor and that of legendary Chicago gangster Al Capone. Both were big personalities who made a living through unsavory means.
“A gangster doesn’t have to be somebody that’s tough,” Lee says. “But you can look at a person and know that that’s not a person you should f— with.”

When Lee entered comedy, he was told the gangster moniker wasn’t a wise career move. People might be uncomfortable with the connotations, he heard.

“If you believe in your brand, you don’t give it up just because some people don’t believe it,” Lee says. “I’ve sold drugs, I’ve sold many different things. Now I’m just selling myself — and I’m not selling myself short.”

Howard Theatre, 620 T St. NW; Fri., 8 p.m., $20-$25.

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