"Heartless" is a song by American hip hop artist Kanye West, released on November 4, 2008 digitally as the second single for his fourth studio album, 808s & Heartbreak. It debuted at the number four spot on the Billboard Hot 100 where it eventually peaked at number two and reached number-one on the Billboard Hot Rap Tracks and U.S. Hot 100 Airplay chart.

The song came to be covered by numerous artists, most notably by Denver-based piano rock band the Fray, American Idol season 8 winner Kris Allen, and singer-songwriter Dia Frampton (runner-up of season 1 of The Voice), with all three versions managing to enter charts in the absence of a physical single release. "Heartless" is one of the best selling singles of all time, selling 5.5 million digital copies in 2009.

On his fourth studio album 808's & Heartbreak and in the pop song "Heartless", Kanye West utilized the voice audio processor device known as Auto-Tune. West had previously experimented with the technology on his debut album, The College Dropout, for the background vocals of "Jesus Walks" and "Never Let Me Down." The voice altering device created a unique sound helping West express his then feelings of his break up with fiancée Alexis Phifer months after the untimely passing of his mother. The pipe-organ sound was sampled from The Alan Parsons Project song Ammonia Avenue.

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