Inside the Kanye West HBO Comedy That Almost Was
by Michael Schneider
Kanye West, HBO sitcom star? It almost happened. Long before the notorious moment he grabbed the microphone from Taylor Swift at the MTV Video Music Awards or celebrated the birth of his daughter with reality-TV scion Kim Kardashian the hip-hop icon headlined a comedy pilot from Curb Your Enthusiasm executive producer Larry Charles.
The sitcom was shot in 2007 but quickly fell by the wayside after an executive shuffle at HBO. Later that year, West’s mother, Donda, died, and the superstar departed on a global concert tour, leaving the TV project behind. It was all a distant memory until this summer, when clips from the pilot started popping up — first on YouTube, and then at a comedy show in Brooklyn, where a bootleg copy of the entire episode was screened.
In the untitled Kanye West comedy project, West played a version of himself, surrounded by a chaotic team of handlers and hangers-on. Patterned after his real posse, the ensemble included Kym Whitley as Kanye’s mom; J.B. Smoove as Kanye’s manager, based on West’s real life manager, G Roberson; Wyatt Cenac as K.C. — which stood for “Kanye’s Cousin”; and rapper GLC as his bodyguard. West’s real-life assistant, Don C., played himself.
Charles — whose credits also include Seinfeld, Mad About You and Entourage — sat down with TV Guide Magazine to recount the West pilot. Whitley, Smoove, HBO programming president Michael Lombardo and Curb‘s Jeff Garlin, who made a cameo in the half-hour, helped fill out a brief history of the path almost taken by music’s most controversial star.
West harbored TV dreams for years, meeting with NBC executives in the mid-2000s, just as he was breaking as an artist. But things didn’t pan out at the Peacock network. West, a huge Curb fan, next sought out Charles.
Larry Charles: They got in touch with me and said, “Kanye would like to meet you.” I couldn’t imagine what we had in common at all. The first thing he said to me was, “I’m the black Larry David.” He started telling me these stories about how often he puts his foot in his mouth, how often he’s apologizing like the way Larry does on the show for saying the wrong thing or being inappropriate. How he doesn’t really want to be that way, he just sort of is that way.
I proceeded to hang out with him. We would go out to get a bite, and sure enough, he would say the wrong thing to the waiter, inadvertently insulting them and having to apologize, and then it would escalate. I started to see a show here.
J.B. Smoove: I met Kanye at the Improv in LA. He was at one of my comedy shows. Before he became the Kanye he is now. He told me he was a fan of my comedy. And since then we became friends. We ran into each other at Saturday Night Live, and then they called me for the pilot.
Kym Whitley: I got close to his mother. I met her to see how to portray her. We went on a cruise. I got to know Kanye and all his friends too. His girlfriend was on set. I think people get him wrong. Everyone is a little cuckoo when it comes to genius.
HBO gave Charles $400,000 and five days to shoot the pilot. Charles saw an opportunity to hire a diverse crew behind the camera as well.
Charles: HBO, it wasn’t like they were super excited. They gave us very little money. But I will embrace that. If I think we can do something great and this is the only was we can do it, let’s try.
Kanye was very open to it. And in the way Seinfeld was smart about this and Jack Benny was smart about this, he was not afraid to have the people around him be really funny and be a straight man for them.
I didn’t want it to be the black Curb. I wanted to give it a structure and a vibe that was more true to Kanye and his world than the Curb style. We wrote an outline, and except for certain lines that needed to be said, improvised a lot of it. But you’re improvising with 10 people, which was a great challenge. I like getting into this Altman-esque thing where there are a lot of people going around talking and overlapping. Because that’s Kanye’s world, that kind of barely contained chaos.
The show starts off with Kanye and his entourage crammed into a van. As Smoove improvises about trying to find Kanye some food and breath mints, the rapper looks overwhelmed. Later, they wind up at an autograph signing, populated by rabid fans.
Charles: I think the pain is where the humor comes in. He is funny. He’s not funny in the same way that Larry David’s funny or JB Smoove is funny. But he’s a great foil.
Smoove: I remember one moment in the van, I went on a 20-minute rant about nothingness. And we did one long take, and everyone was trying to hold it in and we were just laughing as a group.
Whitley: Kanye was on his mark. He listened. And he had some acting chops. I want to see it again now.
Charles: It was a lot of wide-angle stuff, the sense of what it’s like to be in Kanye’s world and just have people coming at you all the time. We did that autograph signing; those are real people, for the most part.
The pilot includes multiple flashbacks — such as West recounting the time he refused to give Tom Cruise a song for Mission: Impossible, until he met the actor (played by a lookalike). In another scene, Kanye is adamant that he’s never been to a certain hotel — but in a flashback, we see him in one of the rooms, having just been robbed by a woman whom he’d brought upstairs.
Charles: True story.
Jeff Garlin: I did a couple of little scenes where I played a white guy walking around. I spent the day with Kanye. I do watch what he does and wonder sometimes, “What are you thinking?” But in terms of my actual interactions with him, he was very pleasant. I sat with him at dinner one night with Tom Cruise and J.J. Abrams.
At the end of the pilot, Kanye makes an awkward visit to a Make-A-Wish Foundation kid, where he’s asked to tape a video greeting for the organization. It’s perhaps West’s best line of the pilot: “Yo, whattup to all the dying kids. I know y’all my dawgs. And you know, all dogs go to heaven!”
Charles: It’s interesting in light of where his life and career and public persona have gone since. I think he was interested at that time in trying to reconcile the private and public version of himself. We had a great shoot and in the end, HBO didn’t pick it up.
Michael Lombardo: We probably gave them a little money to shoot something. But I don’t remember it. He’s pitching something to me right now. I didn’t think I’d ever been in business with him before.
Charles laments what could have been: One episode might have addressed the Taylor Swift debacle.
Charles: The hope was we’d follow him around, be able to shoot a lot of verite stuff like at awards shows, and pick that up and then draw stories from around that. Blur that line between the fiction and reality. Things would be very different today — I can’t say better or worse, I don’t know, but certainly different. I can see he abandoned that course of exposing himself and instead retreated behind the Kanye image. [The pilot] immediately unraveled once it was over. He’s in a very different place now.
Whitley: Imagine if we did that pilot now. First of all, we would get picked up. And it would be a hit show. It would have explained a lot. But the sad part of it is I would not be on it. Because I played his mother.
Smoove: I love his honesty. I think the pilot would give a good interpretation of who Kanye is.
Charles ran into West on a flight last year.
Charles: I hadn’t seen him in quite a few years. We hugged and hung out and talked on the plane. This was before the election, and he was talking about being for Romney and all this crazy stuff. In his Kanye way of being provocative. And then he started to talk to me about this new company he wanted to start, Donda Communications, named after his mother. He wants to be Kanye, media mogul. He wanted to show me his website — he was proud of it. It’s incredibly elaborate. But communications was spelled wrong. No one in his world had told him. That’s Kanye. Very ambitious, very smart, but somewhat insulated from the world.