Devon Shepard met Jenji Kohan, the creator of “Orange Is the New Black” and “Weeds,” twenty-four years ago, when they were writers for the NBC sitcom “The Fresh Prince of Bel-Air.” Shepard, a former standup comedian, got into the business serendipitously, after he clowned on a square producer at a black barbershop in Los Angeles. Kohan, who had recently graduated from Columbia, was a rung down from Shepard—a “baby writer,” in Hollywood lingo. But “she was fun, a whole lot of energy, a sponge,” he said. Kohan wanted to learn dominoes—the “loud and outrageous” street version—and they began playing bones in an office they shared, trading stories about growing up black in South Central and Jewish in Beverly Hills. “I made the room cool,” Shepard said. “People were, like, ‘What’s going on in there?’ ”
This was in 1993, a year after the L.A. riots, and at “Fresh Prince,” which starred Will Smith as a Philly street kid sent to live with rich relatives, the writers’ room was a toxic mess. The staff—which included Smith’s bodyguard and his cousin—kept crazy hours and fought non-stop. There were cruel pranks: someone peed in a colleague’s bottle of tequila. Kohan was one of two female writers, and the only white woman. Her nickname was White Devil Jew Bitch. Shepard was one of her few allies.
After “Fresh Prince,” they lost touch. In the mid-nineties, he wrote for “MADtv,” and she wrote for “Tracey Takes On . . . ”—wild, subversive sketch shows. Then, in 2004, Shepard’s agent handed him a script for a cable series about a pot-dealing single mother. One character, a black supplier named Conrad Shepard, echoed elements of Devon Shepard’s life story: Devon had dealt weed, even while working on “Fresh Prince.” He loved the script, which had no writer’s name on it, and told his agent, “I gotta be on this show.” The agent asked him if he knew the creator: Jenji Kohan. Shepard said, “Do I fucking know her? If your white ass don’t put me in the room, I’m gonna choke the shit out of you.”
Shepard wrote for “Weeds” for three years. Kohan was a dream boss, he said, because she was just as curious, energetic, and easily bored as she had been on “Fresh Prince.” “Jenji has A.D.D.,” he said. “It was like having a class clown as your boss.” The writers played hours of online poker, and to open things up Kohan issued weird challenges: “She would say, ‘I want you to end each scene with a curse word and then start with a curse word.’ Or ‘Have someone hold a cup, and then have a cup go through the whole episode.’ ” Shepard was used to being pigeonholed; at job interviews, he was told, “If we add a black character, we’ll call you.” Although, to his frustration, many people thought that he was responsible for the black dialogue on “Weeds,” he actually wrote more scenes for the white main character, who was played by Mary-Louise Parker. Kohan wrote for all the characters, including Conrad and Heylia, another African-American supplier. In Shepard’s view, empathy and talent outweighed identity. Outsiders could sometimes take bigger risks, because they were less constrained by the burdens of representation. “The person inside the party is always going to have a different perspective than a person looking in the window,” he said.
To break up the monotony, he and Kohan playacted an imaginary TV show called “Djembe,” about an African man who was married to a white suburban woman. The gag eventually made it into an episode. The premise was that Djembe couldn’t speak, and communicated by banging on a drum. “You would have thought we were all fucking crazy and racist,” Shepard said, cracking up at the memory. “We were just so free.”
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