Chappelle moves to New York City and is immediately booed off the stage during the Apollo Theater's famous "Amateur Night" showcase. "That night was liberating," he would later tell Inside the Actors' Studio host James Lipton, "because I failed so far beyond my wildest nightmares of failing, that it was like, Hey, they're all booing. My friends are here watching, my mom, and this is not that bad. After that, I was fearless." He learns to work crowds at comedy clubs at night, and plays to strangers in Washington Square Park on weekends. He signs his first TV development deal at age 19.