Year: 2009

Unlike most of the people on this list, Kid Cudi's breakthrough at SXSW didn't come from a solo showcase. During Kanye West's show at the Fader Fort, Ye opened the stage to his G.O.O.D. Music family including Common, Consequence, and Erykah Badu. The standout from the show, however, was the Kid from Cleveland with vocals featured on Kanye's most recent album at the time, 808s & Heartbreak. Kid Cudi performed "Day 'N' Nite," "Welcome To Heartbreak" alongside Kanye, and "Buggin' Out (2009)" with Consequence. He also made a surprise appearance at the Fool's Gold After Dark party that week and the rest was history.

That fall, Cudi was featured on Jay Z's Blueprint 3, he landed a Complex cover, he was honored by BAPE with his very own t-shirt, and his debut album Man On The Moon: The End Of Day was released. Five years later, Cudi's got five albums and he's currently starring in a new movie alongside Aaron Paul.