One of hip-hop's most popular artists today, Kid Cudi has gone from a buzzworthy blogger's darling to mainstream pop sensation in just five years. Debuting in 2008 with his mixtape A Kid Named Cudi, he was mentored by Kanye West and Jay-Z, who used him extensively on their smash albums 808s and Heartbreak and The Blueprint 3. If you're already down with Cudi's ultra-weird style, you're gonna love this.