He was the kid in pink polos and backpacks, the one who deviated from the ubiquitous “gangster” persona. He was kind of a goofball. He possessed a real underdog story—when he rapped about “Big Brother,” those of us stuck in the shadows could immediately relate. He made crowd-pleasers: College Dropout and Late Registration is full of party staples, and, when his string of hits peaked with Graduation and the mega-successful Glow in the Dark arena tour, you can easily make the case that Kanye was the most loved rapper in the country. He had taken conscious rap to the mainstream, but he wasn't afraid to couple the introspection with a hit. He had opened up rap for middle-class kids like Drake and Kid Cudi, who were similarly unafraid to make songs without traditional hip-hop braggadocio. Hurricane Katrina controversy aside, Kanye was peerless.
Which brings us to 2008, and this HBO pilot. The idea of a Larry David-esque show starring a self-aware Kanye would be absolutely unthinkable now. But back then? West essentially acted in this early Def Poetry performance, and it's spellbinding. He was also amazingly popular. Maybe he could pull it off.
He couldn't! At all! The clip is brutal, the sitcom setup painful. This is early, indisputable proof that Kanye always finds trouble when he reaches into the worst of his bag of tricks: His humor.