On his album "808's & Heartbreak" and in the song "Heartless" West used a very popular vocal pitch device called "auto-tune" made popular by singer/rapper T-Pain and has a "reggaeton-ish" feel. The voice altering device created a unique sound helping Kanye West express his then feelings of his break up with fiancée Alexis Phifer months after the timeless passing of his mother. The song was performed for the first time in Denver, Colorado. The song was also performed at a T.I. concert at Key Club in Los Angeles. Kanye made a special guest appearance and confirmed the song's future release as a single at that show. A snippet of the unmastered version of the song was leaked onto the Internet on October 12, 2008. This was followed by a full unmastered version of the song being posted on West's official blog on October 15. The song was released on iTunes on November 4, 2008. On November 8, 2008, Kanye posted a new mastered version of the song on his official blog. A free link to download the song was posted there as well.
In the U.S. on the week of November 13, "Heartless" made a "Hot Shot Debut" at #4 on the Billboard Hot 100, selling 201,000 downloads in the United States alone and making it his second highest debut on the chart. The single fluctuated in and out of the top ten for two months before reaching a new peak at number three in mid-January, and rose to two in mid-February. In early March it also reached number four on the Pop 100 chart. It is West's second consecutive top five hit on the Hot 100, and his second consecutive song to debut in the top five there. This makes 808s & Heartbreak the first West album to contain two Hot 100 top five hits. On Hot R&B/Hip-Hop Songs, it peaked at four. It debuted at number eleven on the Hot Rap Tracks and has managed to reach number-one in late January. As of September 2012, the song has sold over 4 million paid digital downloads in the United States, becoming West's second song to reach that mark, the first being "Stronger".
In Canada it also made a "Hot Shot Debut" at #8 on the Canadian Hot 100, also based on huge amount of downloads in the country. On 1 December 2008, the song debuted at #63 on the Australian ARIA Singles Chart. It reached #6 on the New Zealand RIANZ chart. On the UK Singles Chart, the song debuted at number #45 and reached #10 due to album download sales. The official digital release date for the single was 12 January 2009. On the Irish Singles Chart the song has peaked at #10.
Directed by Hype Williams, the animated music video for "Heartless" pays tribute to Ralph Bakshi's 1981 film American Pop. It features use of rotoscoped animation, in which actual people were filmed and visual effects studio Opticflavor drew over their every movement, and references various scenes and backgrounds from the film. The video portrays West wandering through a city alone at night, with scenes of various women shown throughout the video. The video also takes place in West's actual apartment den, where The Jetsons portraits are located. West stands by the Astro portrait in five scenes of the video. It was the first animated video directed by Williams.
American rock band, The Fray performed a cover of "Heartless" for their Live Lounge performance on February 16, 2009. Following the premiere of their rendition on BBC Radio 1, it began to receive an unprecedented amount of radio airplay. The track was later included on their Live from SoHo album released onto iTunes on April 7, 2009. In absence of a single release, the band's version of "Heartless" managed to enter the BillboardHot 100 at number seventy-nine on May 21 based solely on downloads. The song has since became a staple at The Fray's live shows and sold over 125,000 downloads in the United States alone. Due to overwhelming public demand, it was released as a digital single in the UK on September 14, 2009. The song was also included in the deluxe edition of their sophomore self-titled album, which was released on November 10, 2009.
A music video of The Fray's version of "Heartless" was released on September. The video showed a classroom full of elementary-level students with the video centering around one boy. He keeps glancing at a girl, as drawings appear on a piece of notebook paper in front of him. The band members as well as Kanye West are seen as simple drawn figures performing on the paper. Eventually, the artwork expands out to the classroom, forming a design around the girl. The video implies that the girl was the 'heartless' one who hurt the boy.
An acoustic interpretation of the song was performed by American Idol season 8 winner Kris Allen as his personal pick for the Top 3 night of the show's eighth season. His performance was praised all across the judge's panel and by other critics, who called it "inventive".Randy Jackson stated that he preferred it to West's original and The Fray's cover version while Simon Cowell said, "I had written you out of the competition but that has changed after that performance." A studio version of the cover was temporarily made available on iTunes the following week. The performance helped him move on to the finals and win. His version of the song debuted at #16 on the Billboard Hot 100 chart in May 2009. Allen has also performed the song during the American Idols LIVE! Tour 2009 with a more alternative rock-oriented sound. Allen re-recorded the song for his self-titled debut album. Allen also released the album version of the song as his second single in New Zealand. During tour, Allen also did a mash up of this song and Gangsta's Paradise by Coolio.