The 50 Best Kanye West Songs Ever

9. Heartless

Release Date: Novermber 5, 2008

Album: 808s & Heartbreak

Writer(s): Kanye West, Ernest Wilson, Scott Mescudi, Malik Jones

Producer(s): West, No I.D.

Notable Lyric:

“You run and tell your friends that you’re leaving me

They say that they don’t see what you see in me

You wait a couple of months, then you gonna see

You’ll never find nobody better than me”

There’s probably no wider gulf in Kanye’s output than the one between Graduation and 808s & Heartbreak, both from an aesthetic and thematic standpoint.

While Graduation’s big sound was whittled down considerably for the follow up record, Kanye himself seems to have been (temporarily) humbled as well.

“Heartless” stands out as the best example of that contrast on 808s. It’s no surprise that it was by most measures the most well-received track on the album.

Like every other song on that album, it’s stripped down sound compliments Kanye’s self-pity and victimization. While he’s never had much of a problem with being honest, here Kanye actually sounds exposed and vulnerable.

One of the peculiar things about the song, and really any other time that Kanye has openly dealt with his own psyche, is that by casting himself as the victim he’s actually doing more to show off his own insecurities. It’s as if Kanye creates a character to belt out these bars, someone who is too dense to appreciate how much he is complicit in whatever heartlessness resulted in his pain.

Next: 8. Stronger