Heartless

Kanye West first played a rough version of "Heartless" at the 2008 Democratic National Convention, then posted an unmastered clip to his blog in October. The song became the second single from 808s & Heartbreak, an album built on grief after his mother's death and his breakup with fiancée Alexis Phifer. West originally wrote the track for Jay-Z's The Blueprint 3 but kept it after a studio session where the melody clicked.

Built on heavy synthesizers and Auto-Tune, "Heartless" is a pop ballad that strips away West's earlier sample-heavy style. The minimalist production lets the lyrics about numbness and betrayal sit front and center. Critics called it bleak and beautiful, with Rolling Stone naming it one of West's best. It peaked at number two on the Billboard Hot 100, kept from the top by T.I.'s "Whatever You Like." The song has sold over seven million copies in the US alone, earning a 7x Platinum certification.

The music video, directed by Hype Williams, uses rotoscoped animation as a tribute to Ralph Bakshi's 1981 film American Pop. It shows West wandering a monochrome city with a cartoon character, haunted by memories. Kid Cudi and Mr. Hudson make cameo appearances. The video was nominated for Video of the Year at the 2009 BET Awards and has amassed over 200 million YouTube views as of early 2025.[edit]