We’re riding along with Kanye West in his Escalade. West is playing a barely fictional version of himself. Comedians sit next to him and behind him in the SUV limo, including Kym Whitley, Wyatt Cenac and JB Smoove, playing members of West’s entourage in a 2007 TV pilot for HBO designed with aims of becoming not just West’s Entourage, but also his Curb Your Enthusiasm and his Sex and the City.
If it sounds like the start of an ambitious failure, then you guessed right.
Some footage from the half-hour pilot bounced around the Internet last week. Last night, Cenac surprised audience members at his weekly Night Train comedy showcase in Brooklyn with a screening of the entire half-hour.
The pilot episode, submitted Aug. 9, 2007, and titled “A Little Inappropriate,” imagines West and his entourage attending a signing event, then visiting a Make-A-Wish boy in a hotel room — all along the way, West meets unruly fans and strangers, from an ignorant young racist of a limo driver, to a would-be rapper, to the Make-A-Wish coordinator who insists on mispronouncing Kanye as Kenny. There’s plenty of awkward moments played for pauses by West and executive producer Larry Charles. There also are several genuine laughs.
Cenac played K.C., as in Kanye’s Cousin. “It was a partially scripted show,” he explained. “I guess they were like, ‘Fuck it.’ Partially scripted means the names, too.”
“He kept talking about Curb Your Enthusiasm,” during shooting of the pilot, Cenac said of West, “but he was also like, ‘This is also like my version of Entourage. This is my Entourage.’ So it was his Curb, it was his Entourage, and then, he was like, ‘I want this show to be for fashion, what Sex and the City is, for like women’s clothing, I want this show to be the men’s version of Sex and the City. So in a way he was trying to capture every HBO show.”
Cenac said West focused attention on the details of what everyone in the cast was wearing — for Cenac’s character, West figured his fictional cousin would be wearing the rapper’s hand-me-downs. Kanye also brushed up on his comedy skills.
“To get ready for the show he took improv classes,” Cenac said.
“Where?” asked Questlove from The Roots, whom Cenac had invited onstage to deconstruct Kanye’s HBO pilot screening with him.
“Matt Besser from Upright Citizens Brigade would come to Kanye’s house…
“So Kanye didn’t go to UCB. UCB came to him.” Questlove said. “Was Amy (Poehler) with him?”
“No. It was just Matt. And then Matt brought me. That’s how I got the part, was because Matt brought me. And then, Kanye cast two of his real-life friends in it. His road manager, Don, and his former bodyguard, who’s also a rapper, named GLC. And so, I would go. And GLC was never there. But it was me, Kanye and Don, all doing improv together. With no audience and feedback, and they never wanted to get off of the couch. So imagine Whose Line Is It Anyway? but in a car.”
“The other thing I will say in Kanye’s defense,” Cenac added. “He knew he was not a good improviser…He read something that Seinfeld said about surrounding himself with better talent. And that he would rise to the occasion. So that was his hope, that he would surround himself with a lot of really talented people, and that he would eventually, he would have to work to match that. But prior to that, what he did when we were shooting. There were would be a lot of scenes that had important story details that needed to get out, and he didn’t trust that he could do it, so he’d be like, ‘Have them do it.’ And so they would pass off a lot of stuff. That’s another reason it was an hour long. There wasn’t a lot of Kanye in it. There was a lot of everybody else. And HBO was like, ‘Yeah, we didn’t pay for a show with these no-name motherfuckers. Find a way to put some Kanye in this.'”
Kanye also wanted to put some Tom Cruise in his pilot episode, but had to settle for a body double in a flashback scene.
West and Charles initially submitted an hourlong cut with segments of an altogether different nature, with people like Nelson George, Boyce Watkins and Cornel West. “They weren’t part of the story. They were just interviews, to talk about music,” Cenac said. To Questlove, he added: “If the show were still on, they’d probably just have you read a chapter from your book.”
Larry Charles would go on to use JB Smoove that fall in the sixth season of Curb. Cenac went on to become a correspondent on Comedy Central’s The Daily Show with Jon Stewart. And Kanye West went on to make more records, and this year make a baby with Kim Kardashian.
Questlove, wearing a T-shirt with the iconic movie image from Titanic repurposed to show Kanye and Kim Kardashian at the front of the ship, jokingly wondered if the Kardashians would have crashed on over to Kanye’s HBO show at some point, too.
But that’s an alternate reality that never happened.
As for the pilot Kanye West did complete? “It’s not the best thing HBO made. But it’s not the worst,” Cenac said. “It’s hard to top John From Cincinnati.”
Considering John From Cincinnati was on HBO’s airwaves that same summer West submitted his pilot, it’s amazing the cable network didn’t green-light a career in TV comedy for the self-proclaimed “black Larry David.”