Welcome to Heartbreak

The song features a guest appearance from Kid Cudi on his debut collaboration with West, as well as background vocals by Jeff Bhasker.

[5] West further pens about how he wishes to get married and have a family, but numerous reasons in his life have kept him from doing so; he classifies the song as "the first time a rap artist spoke condescendingly about property, possessions like a sports car".

[5] In an interview for American singer Pharrell Williams' OTHERtone show on July 10, 2016, Kid Cudi revealed the song's hook originated from a melody he wrote for fellow rapper Jay-Z's eleventh studio album The Blueprint 3 (2009).

[4][11] The song's intro utilizes a cello that was played by James J. Cooper, III alongside Jennie Lorenzo, and was described by The Washington Post as reminiscent of an organ.

[4] In the lyrics of "Welcome to Heartbreak", West addresses attempting to fill his life's lack of substance with lavish materialistic items, expressing a struggle to relate to a normal lifestyle as a result of his fame.

[9][14] West echoes the rapper by singing the line "I can't stop having these visions" towards the end of the song, alluding to the death of his own mother.

Writing for Urb, Brandon Perkins commented that the song is where West sets "his prized possessions against the simplicity of 'real life'", noting he uses a "disconnected yearning" to mark his juxtapositions.

[22] Adam Conner-Simons from musicOMH observed how West does not "hold back" on the song, using the lyrics for "reflecting on his party-heavy lifestyle and envying his friends' picket-fence existences".

[23] Reviewing for IGN, Alfred H. Leonard, III stated that West is assisted by Kid Cudi in struggling "to relate to the fruits of living a normal life" due to having a celebrity lifestyle.

[24] The staff of NME pointed to the song's "tortured opening cello groans" as providing clearness that West still possessed "his marbles" in 2008, following on from disappointing events in the artist's career throughout the year.

[25] They further noticed how "a cold, metallic bleakness" is present on the song, which invokes "cinematic flashes" in the manner of the 1987 film The Running Man that stars Arnold Schwarzenegger, as well as empowering "the woe-is-me slush".

[25] Voicing a less positive response, Wilson McBee from Slant Magazine was thankful for Kid Cudi's "anxious cooing" on the song, which serves as "a perfect counter" to what he dubbed "West's attenuated sketches about fame and self-loathing".

[26] In a mixed review of "Welcome to Heartbreak" for Digital Spy, Mayer Nissim called the song an "introspective slice of hip-pop" mostly performed via Auto-Tune and said that despite there being nothing wrong "with West using the available technology to transform his voice", it has become "horribly ubiquitous" in the years leading up to 2009.

[12] He elaborated, glorifying the "beautifully understated" beat and labeling the song's lyrics "fine", but pushed for it being hard not to worry that the Auto-Tune "give[s] the track a 'Made In 2008' stamp that could make it close to unlistenable in a few years' time".

[35] The music video for "Welcome to Heartbreak" was released on February 18, 2009, via West's blog, and was directed by Nabil Elderkin, who received credit mononymously under his forename.

[20] West was referring to the video for American synth-pop band Chairlift's "Evident Utensil", directed by Ray Tintori; Nabil dubbed it as "data moshing" in an MTV News interview on February 18, 2009.

He elaborated, recalling shooting certain scenes "in super-slow-motion" with the Phantom merely for "transitional movement and textures", going on to state he was certain the song needed a music video.

Of creating the video, Nabil recounted West taking a liking to his initially presented idea, before he "nagged" the artist slightly about it.

[37] Filming Personnel While showcasing artists signed onto his GOOD Music imprint for South by Southwest (SXSW) at the Levi's/Fader Fort on March 21, 2009, West brought out Kid Cudi.

[43] For West's two night concert of 808s & Heartbreak in its entirety at the 2015 Hollywood Bowl in September, he and Kid Cudi performed the song as the set's second track.