then travelled to Hawaii to work with rapper Jay-Z on his eleventh studio album The Blueprint 3 (2009), before West decided on transferring to recording for 808s & Heartbreak in the state once "Heartless" had been made.

[2] The two of them co-wrote it with Malik Yusef and fellow rapper Kid Cudi, the latter of which was revealed to have penned the chorus in his documentary film A Man Named Scott (2021).

[4] West premiered "Heartless" with a performance at the 2008 Democratic National Convention (DNC) in August, before he confirmed its release as the album's second single at a concert of rapper T.I.

[30] On October 28, 2008, the song was released to US rhythmic contemporary radio stations as the album's second single by West's record labels Roc-A-Fella and Def Jam.

[18] Balls elaborated by writing that even though creating the album "seems to have served as an alternative form of therapy" for West, the "terrific" song demonstrates how "the soul-bearing has propelled him to new creative peaks".

[18] Alex Macpherson from The Guardian pointed out how the song includes a "solipsistic and clumsy" take on "the solitude of the superstar", noticing West provides a "testament to his talent" by ultimately executing it.

[33] Reviewing the album for Entertainment Weekly, Leah Greenblatt commented that the "stuttering" song is among its understandably dominant "mournful tales of heartbreak", noting a confession from West.

[34] The staff of NME viewed the song as fulfilling the promise of West "leading the assault" on the planet undertaken by "scowling hip-hop androids", which he makes on the previous track "Welcome to Heartbreak".

[12] They explained, citing how the former is the only track to include rapping from him and saying the "cathedral organs and lava-lamp rhythmic thuds underscore a dancehall-style tormented chorus that impacts with flooring intensity".

[35] USA Today's Steve Jones picked the song as one of tracks from 808s & Heartbreak to download, an opinion that was shared by the staff of The Observer and Alfred H. Leonard, III of IGN.

[39] In a lukewarm review at Pitchfork, Scott Plagenhoef characterized "Heartless" as a "very good" song that is a surprisingly appropriate fit for "the car radio" while naming it merely a "second-tier" single from West.

[13] Wilson McBee from Slant Magazine described the song as having all the qualities "of a classic, minor-key club anthem, darkly swaggering and indulgent of love's travails", though wished that it was performed by Usher instead.

[24] That same year, the track was ranked by Teen Vogue as the 47th best breakup song for the newly single, with Kristi Kellogg estimating that it will be played repeatedly "when you're in the post-breakup anger phase".

He emphasized the challenge as "a daunting task" that over 3,000 frames of hand-drawn animation and backgrounds were utilized for, though said that they managed "to pull it off in a record of 10 days working around the clock" with assistance from "a very talented team".

Williams expressed his position for the video, asserting that he and West desired "to do something ... that was unexpected" and said they "needed a visual effects team that would deliver in terms of style, quality, and timing".

[56] Cesar Cueva of Art of the Cartoon felt both surprised and pleasured about the music video being animated, revealing himself to have instantly found the rotoscope style impressive.

[51] Cueva further wrote that after sensing a homage "to something I had seen before" with the video and having this confirmed by West citing inspiration from American Pop, he appreciated it more, and praised the sitcom portraits.

[88] The song further reached the top 40 in Ireland,[89] Sweden,[90] Denmark,[91] the Netherlands,[92] and Germany,[93] with it receiving a double platinum certification by IFPI Danmark for 180,000 shipments in the third of the five countries on April 3, 2024.

's Myspace sponsored concert at the Key Club, Los Angeles, in October 2008, West announced that 808s & Heartbreak had been finished in Hawaii and the song would be released as a single.

West also said that his grandfather "drove the first car in the marches out of Oklahoma" to see the ball, before he sang an altered version of the song's chorus in tribute to both the civil rights struggle and Obama: "In the night I hear them talk/ The greatest story ever told, [...] Somewhere far along this road, a new soul: Obama ..."[102] West performed a medley of "Heartless" and "Pinocchio Story" as the eighth number of his February 2009 VH1 show, which was later issued as his second live album VH1 Storytellers in January 2010.

[103] He responded to rapper 50 Cent's comments about him being dressed differently in a Paris picture and addressed people who disputed his sexuality during the performance, remarking "look at me now, singing on the ground with my pink shirt on" and questioning, "Does this look gay to you?

[107] West performed the song during his headlining set at the 2011 Coachella Festival, during which the pitch shifting was handled by the concert's programmer Laura Escudé for enabling him to be heard as the Auto-Tune was turned on and off.

[109] On February 25, 2014, West performed a five-minute medley of his greatest hits in chronological order by album on Late Night with Seth Meyers, which included "Heartless".

He finalized by opining that West "almost mak[es] light of the fact that there was real heartbreak there", considering it like "the teacher that whispers instead of yelling" due to converying a point "with more reservedness than straightforwardness".

[130] Singer Dia Frampton covered the song for the first live show of American competition The Voice on June 7, 2011, and played piano lightly alongside rephrasing the lyrics.

[135][136] On November 19, 2015, rapper Post Malone performed a cover of "Heartless" on acoustic guitar for Trevor Nelson in BBC Radio 1's Live Lounge.

[141][142] On September 18, 2018, violinist Brian King Joseph performed a cover of the song for the finale of America's Got Talent's 13th season, utilizing different methods of playing his violin.

[178][184] A writer for BBC Radio 1 saw "Heartless" as great, while MTV's Colin Schoenberger chronicled how the "aching, earnest pop-rock ballad" adopts "a sold life of its own" and believed the Live Lounge performance "begat other fantastic covers".

[183] In a negative review for MusicRadar, Ben Rogerson pinpointed the strangeness of the cover lacking the original's "Auto-Tuned vocal" and sounding "more human" as a whole, yet "com[ing] off significantly less powerful and soulful".

[198] In a phone call with Vulture, Allen cast light on a "small discussion" he had about the cover being removed from the album following West's incident at the 2009 MTV Video Music Awards.