“Heartless” by Kanye West

"Heartless" was the second single pulled off 808s & Heartbreak, Kanye West's fourth album, and it very nearly belonged to somebody else: the track was first meant for Jay-Z's The Blueprint 3 before it was handed to West during the sessions. He wrote it with Kid Cudi, Malik Yusef and No I.D. and co-produced it with No I.D., with Jeff Bhasker on keyboards and Manny Marroquin on the mix.

It's a pop ballad dressed in synthesizers, with hip-hop and R&B bleeding in around the edges, and the heartbreak is his own: West picks over his split with Alexis Phifer. The animated video, a tribute to Ralph Bakshi's American Pop, plays the same breakup as cartoon melancholy. It went to number two on the Hot 100 and seven times platinum in the US.

Written with AI assistance from RockLists chart data, MusicBrainz and Wikipedia.