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Billboard’s Greatest Pop Stars: In 2009, Kid Cudi and Drake Welcomed Hip-Hop to Heartbreak

This Greatest Pop Stars Sidebar looks at singing rappers Drake and Kid Cudi and how they transformed the sound of hip-hop in 2009.

Reeling from his mother’s death, Kanye’s embrace of Auto-Tune and anguish across 2008’s 808s and Heartbreak is frequently credited for the rapper-singer sea change, though he wasn’t without his forerunners — there was Nelly, there was T-Pain, there was “Lollipop,” there were countless others. Cudi’s debut single “Day ‘n’ Nite,” inspired by the death of his uncle, unrequited love, and his nocturnal weed habit medicating it all, went top-five in May 2009. The Toronto native — just two years removed from Degrassi — sparked a major label bidding war behind his 2009 mixtape So Far Gone, eventually won by Lil Wayne’s Young Money empire that June.

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