A vaporwave remix of the song featuring American rapper Lil Uzi Vert was released alongside the deluxe edition of its parent album on March 23, 2020.

[11] Then after a period of silence, on November 24 the single "Blinding Lights" was revealed through a Mercedes-Benz television commercial,[12] with reports of "Heartless" surfacing a day later,[13] along with its leaked cover art.

[15] In an interview with CR Men, the Weeknd confirmed that "Heartless" was the first song that he wrote for After Hours after the release of his 2018 EP My Dear Melancholy.

[16] Lyrically, "Heartless" sees the Weeknd returning to his infamous party and playboy lifestyle after his disappointment with previous relationships.

On a statement discussing the single's position on the list, Jessica McKinney complimented the song's production and its unique vibe.

[21] "Heartless" entered the Billboard Hot 100 at number 32 on the issue dated December 7, 2019, becoming the highest-debuting single of the week.

[25] Christmas songs began overtaking the upper half of the chart on the issue dated December 21, 2019, causing "Heartless" to drop sixteen places to number 17.

[37] An official music video for the Lil Uzi Vert remix of the song was released on April 14, 2020, and it featured a montage of warped FHS footage and an anime version of the Weeknd throughout the visual.

The performance saw the Weeknd descend into the backstage corridors of the Ed Sullivan Theater as the walls of the building bend and shift around him.

[41] Complex's Jessica McKinney said of the collaboration, "After dropping two of the biggest albums of the year so far, it's clear both the Weeknd and Lil Uzi Vert are on a winning streak.