Songfacts®:

• West explained to MTV News why he chose this record as the follow-up to "Love Lockdown." Said West: "Listen to it. That hook is, like, [really] good. I also thought it was good because, first of all, 'Love Lockdown' - if I had rapped on it [it] would've just been a rap song and it wouldn't have sounded quite as different to people as it sounds for some reason. But any rapper would've loved to rap on 'Heartless,' from a Wu-Tang to a West Coast rapper to a down-South rapper. 'Heartless' is a perfect rap beat, and the hook is like straight Broadway melody. The message is just incredible: 'In the night I hear them talk/ The coldest story ever told/ And far along this road he lost his soul.' It could be an opera."
• This samples the title track of The Alan Parsons Project's 1984 album Ammonia Avenue.
• The single's cover art is virtually the same as for "Love Lockdown," but is missing the red heart balloon and is therefore "heartless."
• Kanye West teamed up with the director Hype Williams to create an animated video for this song. Williams previously won the 2006 BET Award for Best Director for West's "Gold Digger."
• In a similar way to "Love Lockdown," West sings on this track using the Autotune software for Pro Tools rather than rapping. In a interview during a press day for 808's & Heartbreak, the Chicago artist described his latest sound as no longer Hip Hop, but "Pop Art."
• In an interview on Big Boy's Radio Show West explained the reasoning behind the Auto-Tune and melody-heavy 808's & Heartbreak. Said West: "I wanted people to take my words into their soul, and have it embedded it their life, spirit and energy. When I was a shorty, they taught us stuff with a melody, like the ABC's. So I'm about to express my stuff with melody. It's a fine line, where you don't know if it's rapping or what it is. It's just what's necessary at the time - what it feels like [and] what the beat makes me do."
• Kanye West told The Observer November 30, 2008 that the song's chorus, which alludes to his feelings regarding the ending of his 18-month engagement to the designer Alexis Phifer and the recent tragic death of his mother has a classic message. He explained: "The Shakespearian tragedy. That's what this is - it's a modern-day tragedy. Devastation. Multiple losses in my life."
• Never one to hold back from blowing his own trumpet, West bragged - sorry, blogged - concerning this song's success: "It doesn't sound like anything else ever made in history! This is a song nobody can front on!!! The beat is on some RZA sh--, and every line could make the ultimate rap hook!"
• An acoustic interpretation of this song that was done on the Live Lounge by The Fray debuted at #79 in the Hot 100 in May 2009. Its chart entry was prompted by American Idol winner Kris Allen's own organic performance of this song as his personal pick for the Top 3 night of the show's eighth season. Once it became available for download the following week, Allen's version entered at #16 in the Hot 100.
• A version by Dia Frampton debuted at #78 on the Hot 100 in June 2011 after she performed the song during the First Live Show of the reality TV series.
• Kanye West performed "Heartless" with altered lyrics at a youth ball for Barack Obama's first inauguration.