"Heartless" was written by West, No I.D., Kid Cudi and Malik Yusef, while being produced by the former two. It was passed on to West during recording sessions, after originally being intended for inclusion on Jay-Z's eleventh studio album, The Blueprint 3 (2009). Following the song's debut at the 2008 Democratic National Convention (DNC), West shared an unmastered version via his blog on October 15, 2008. The song was later serviced to US rhythmic contemporary radio stations as the second single from 808s & Heartbreak on October 28, through Roc-A-Fella and Def Jam. A pop ballad with influences of hip hop and R&B, it features synthesizers. In the lyrics of the song, West reflects on his break-up with Alexis Phifer. "Heartless" received generally positive reviews from music critics, who mostly complimented West's performance. Some placed emphasis on the song's subject matter, while other critics praised the composition. At the 2010 BMI Pop Awards, it stood among the Award Winning Songs. The song reached number two on the US Billboard Hot 100. It further attained top 10 positions in Canada, New Zealand, Turkey, and the United Kingdom. Eventually being certified septuple platinum in the United States by the Recording Industry Association of America (RIAA), the song became one of the highest certified digital singles in the US. It has also received a quadruple platinum certification from the Australian Recording Industry Association (ARIA) in Australia and double platinum certifications in both Denmark and the UK by IFPI Danmark and the British Phonographic Industry (BPI), respectively. - Wikipedia