On "Heartless", Kanye West exemplifies his will to both write great pop harmonies and hip-hop that manages to still be successful and poignant.
Wait a second. So Kanye West can sing, too?
Well, not really. Though on “Heartless", the most commercially successful track to appear on 808s & Heartbreak, the Louis Vuitton Don has a go at some good old-fashion pop R&B crooning, and the result is surprisingly victorious. With the imperative assist from Auto-Tune notwithstanding, West's voice slips back and forth between a seemingly apathetic prose within each verse and the soulful, aching drone of a beautiful chorus in a way that reminds us that the artist still knows how to rap and write a pretty catchy hook at the same time.
That he was able to produce such a track with a minimalist approach to songwriting is astounding. Much like most of the other tracks that appear on 808s, this is a song that beholds an appeal rooted directly in candor. “In the night / I hear them talk / The coldest story ever told / Somewhere far along this road / He lost his soul / To a woman so heartless", the more-infectious-than-the-common-cold chorus announces. But that's not what makes the lyricism great. Instead, the question of “How could you be so heartless?" repeating twice before the hook closes is what differentiates this from being a simple pop refrain and the actual powerful declaration oozing with anger and posterity that it is. Its defiance and frankness translates so well, in fact, it even allowed a band that has made a career out of writing simple pop refrains to sound fresh.
Or, well, kind of fresh at least. Anyways, what makes this track particularly special is something most casual listeners may not recognize at first (or 15th) glance, and that's the frame of percussion the song is fundamentally built around. While “Heartless" is widely regarded as the most accessible (i.e. likable) song that appears on the record, it should be noted that the reasons behind this being the one track those who hate 808s can still stomach has more to do with the song's 4/4 time signature and accented keyboard notes buried within the verses. These aspects were at the forefront whenever West performed the song live around the time the album was released and even more so during his VH1 Storytellers performance.
And finally, there's the remix. The only “official" remixed take on the song was a version that featured a verse from Rick Ross. The result? Failure. Why? Because much like everything else that appears on 808s & Heartbreak, Kanye made it practically impossible to one-up anything about the original versions of the songs that appear here. One listen to Ross' addition, and that's enough to prove how useless anything extra could be when it comes to not only “Heartless", but ultimately the rest of the songs that paint the album.
West broke genre barriers with this record. Yes, this was the hit single. Yes, it sold 5.5 million copies in 2009, making it one of the best-selling releases of the rapper's career. And yes, it reminded everybody that Kanye West still likes to rap, even though those moments appear few and far between on this particular album. But more than anything, “Heartless" was--and still is--a brilliant piece of art that blends pop and hip-hop in a way most other stars could never even dream of. Its willingness to step outside the box of common thinking and formulaic song writing is precisely why this track isn't just a great pop hit, but also a great pop song.