95. White Boy f/ Kanye West, John Legend & Belo (of Do or Die) "You Know" (2004)
Album: No Gray Area
Producer: Kanye West
Label: Icee Records
In 2004, a rapper by the name of White Boy from Rockford, IL was one of the luckiest new artists in the industry. He’d competed in and won a rap contest held by Chicago radio station 107.5 WGCI, and the purse was a single produced by and featuring Kanye West. Ye was red hot coming off the heels of College Dropout, and he hand-delivered White Boy a sure-shot single featuring a then-unknown John Legend and Belo from Do or Die.
The contest was run by the largest urban radio station in the market, so is basically guaranteed airplay—and boy, did it get spins. While the record was basically considered a Kanye West song (Ye did the beat, hook and first verse), it did give White Boy the one and only hit of his short career. Unfortunately, the general public never heard from White Boy after the summer of ‘04—but at least he has a cool story to tell his grandkids.