Charles grew up among those masses, coming of age in the Sixties in a giant Coney Island housing project built by Donald Trump’s father. When he went off to college at Rutgers in the early Seventies, a professor told him that if he wanted to be a writer, he should drop out of school and hit the open road. “Look at me,” Charles recalls the professor telling him. “I could have tenure next year. Instead I’m going to quit and finish my novel.”
Charles took the advice, and he and a buddy began touring hotel lounges and seedy bars as the opening comedy act for a Top 40 cover band. When they were fired over payment disputes, Charles found himself back in New York, where he bumped into his old professor.
“I’ve been traveling the country being a writer,” he told his teacher. “How’s your novel?” Charles recalls him responding, “I took tenure.”
Charles ended up back in Brooklyn, crashing with friends. One had an extensive porn magazine collection, which inspired Charles to write his own humorous, bawdy tales; when he and his friends got high, he would read the stories out loud for their amusement. This prompted him to send a humor piece to a local porn mag, Screw, which published it. “My grandmother in Florida was so proud,” he says. “She’d go to card games and say, ‘Look, my grandson is published.’”
His Screw pieces led to a brief gig writing porno novels in what Charles describes as a sweatshop with typewriters. Later, he took a job as a bellhop at a Catskills resort, and by 1976 he had saved enough to move to Los Angeles. For a year he parked cars and, in between shifts, loitered outside a stand-up club trying to sell jokes to comics. In 1980 one of his customers was hired onto a late-night comedy show called Fridays and recommended Charles for a job.
On his first day in the writers’ room, he met David, a Brooklynite from nearby Sheepshead Bay. “I heard his accent; he heard mine,” David says. “And we were best friends immediately. It was like we had known each other for 10 years.”
Fridays was canceled after three seasons, and it was years before Charles could get another steady TV job. In 1988 he began writing for The Arsenio Hall Show. For six months, not one of his jokes made it on air. Standing outside the show’s offices smoking a cigarette one day, Charles—who by this point had gotten married, acquired a mortgage and had his first child—knew he was about to be fired.
“I was looking up, going, ‘What should I do? Give me a sign,’” he says. Just then, he saw a Mercedes convertible driving toward him. Jack Nicholson was at the wheel. The movie star slowly passed the soon-to-be-unemployed gag writer. “He looks at me,” says Charles, “and I look at him. And for whatever reason, we both just burst out laughing. And he says to me, ‘Yeah, it’s funny,’ and just keeps on going.”