Kanye West
The concept of being an underdog is one the Chicago rapper knows all to well. From ghost producing to get a foot in the game to literally standing on tables to get his rhymes heard, West easily deserves a spot on this list. He arrived during a time when gritty, street rap was the preferred sound. No, he wasn’t signed to an indie label; he was with Roc-A-Fella, and literally thought to be an experimental signing.
Even after attaining success, Yeezy’s infamous comments about George Bush and the Taylor Swift fiasco should have bodied him.