Heartless

Where they were

Released on November 5, 2008, 'Heartless' came during Kanye West's transition from a commercial powerhouse to a more introspective artist. This track was part of his fifth studio album, '808s & Heartbreak', which followed the critically acclaimed 'Graduation'. At this point in his career, West was grappling with personal loss and artistic reinvention, moving towards a more electronic and emotionally charged sound.

Why it matters

'Heartless' received significant acclaim, peaking at number 19 on the Billboard Hot 100 and earning a Grammy nomination for Best Rap Solo Performance. The song's innovative use of auto-tune and its exploration of heartbreak influenced a wave of artists in hip-hop and pop, marking a pivotal moment in the evolution of contemporary R&B and pop music.

Essential tracks

• "Heartless" — As the lead single, 'Heartless' encapsulates the album's themes of loneliness and heartbreak while showcasing West's signature use of auto-tune.