‘This Is Pre-Kardashians.’ Seinfeld Writer Recalls What It Was Like Working With Kanye West, And Weighs In On His Recent Controversies
What was it like working with Ye nearly two decades ago?

Kanye West has become a polarizing figure, with some of his fans avidly following the work he does and others taking issue with his controversial actions and statements. Years ago, though, West was arguably known more for his music as well as his tendency to pop up in TV shows and movies. The hip hop icon even worked with veteran Seinfeld writer Larry Charles on a project that was set up at HBO. Now, Charles is reflecting on what it was like working with West before his romantic involvement with (and divorce from) Kim Kardashian.
Larry Charles’ list of credits is vast, as he’s written and/or directed for shows like Mad About You, New Girl and Curb Your Enthusiasm (an HBO show people still buzz about). It was in 2008, during Charles’ stint as a scribe on Entourage, that he met Ye. Charles told Page Six that the rapper, who referred to himself as the “Black Larry David” when they first met, was lighthearted at the time and had a solid sense of humor as well:
He was like a sweet, funny, self-aware guy. He was very loose — this is pre-Kardashians. [West] was constantly telling me funny stories about putting his foot in his mouth and having to apologize.
Over the years, especially during the earlier part of his career, Kanye West made several movie and TV appearances (and, with the latter, I’m not just talking about his musical guest appearances on SNL). West cameoed as himself on Entourage and voiced a somewhat fictional version of himself named Kenny West on multiple episodes of The Cleveland Show. The “Jesus Walks” performer also played himself or a character in the films State Property 2, The Love Guru and Anchorman 2: The Legend Continues.
Given how Ye gravitated towards comedy at the time, it makes sense that he would’ve wanted to team up with Larry Charles for a project. Charles explained that he and the Grammy winner were working on a half-hour improvisational show, which would’ve been based on the latter’s life. JB Smoove, whom Charles worked with on Curb, was also set to star in the show. Charles went on to recall the tone of the production and how the dynamic amongst the creative team, ahead of HBO making the decision to scrap the project:
That show was kind of like him. His life as a comical horror story. Everybody got along great. and [West] was wonderful to work with actually. And I even considered him a friend at that point.
Kanye West has lost a few friends (and various business deals) over the years, as he’s come under fire for making antisemitic statements and sharing other inflammatory thoughts. In terms of some of his famous buddies, fellow rapper Pusha-T didn’t mourn the loss of their friendship and, after West made inappropriate remarks about Jay-Z’s kids, that bond seems to be broken as well. Larry Charles – who recently discussed cocaine use in the ‘80s – weighed in on West’s personal problems as well and expressed empathy for him:
There’s all these little things, these little changes in life that sort of have these gigantic consequences. And so, again, he’s somebody who has veered off into this direction and clearly there are mental health issues. He’s a golden goose and golden gooses in Hollywood are exploited. Nobody steps up to help them and take them out of the limelight for a while and get them the help they need. Instead, they continue to exploit them because they can make so much money.
It’s intriguing to think about what Ye’s life and career might’ve been like had certain choices not been made. Admittedly, the show he and Larry Charles were working on also sounds interesting. While it goes without saying that Ye’s public image is very specific today, Charles’ sentiments paint a picture of a young man who was a fan of comedy and a solid collaborator.
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Erik Swann is a Senior Content Producer at CinemaBlend. He began working with the publication in 2020 when he was hired as Weekend Editor. Today, he continues to write, edit and handle social media responsibilities over the weekend. On weekdays, he also writes TV and movie-related news and helps out with editing and social media as needed. He graduated from the University of Maryland, where he received a degree in Broadcast Journalism. After shifting into multi-platform journalism, he started working as a freelance writer and editor before joining CB. Covers superheroes, sci-fi, comedy, and almost anything else in film and TV. He eats more pizza than the Teenage Mutant Ninja Turtles.
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