Hip-Hop's Seven Best Breakup Songs

Jay Z
Jay Z
Photo by Mark C. Austin

Hip-hop gets a bad rap for being overly macho. That's true in large part, but that doesn't mean plenty of rappers aren't intensely sensitive. Putting aside how easily they get their feelings hurt and jump into beefs, there's the socially conscious crowd, the baby-making-music crowd, and even a whole heap of breakup songs recorded by famous rappers.

Unsurprisingly, when rappers are willing to drop their defenses and be vulnerable for a moment, it can yield some pretty awesome results. The emotional weight in words like Ghostface Killah's famous "Jamie verse" on Wu-Tang Clan's "Impossible" is incredible, carried even further by the verbal workout of his flow.

Hip-hop actually contains some of the best kiss-offs and breakup songs ever recorded, despite how incongruous it might seem for our macho rap stars to admit they're heartbroken. These are my picks for the best of the bunch.

7. OutKast, "Roses" An album called The Love Below was almost guaranteed to explore the darker side of these things as well, and our generation's Prince put forth his own "When Doves Cry" with this heartbroken hit.

6. Kanye West, "See You In My Nightmares" Almost any track from Kanye West's last three albums could make this list, but this one is perhaps his best kiss-off, complete with an utterly ridiculous Lil Wayne verse that still stands as one of the best he's ever laid to wax.

5. Ghostface Killah, "Back Like That" With a Jay Z quote and sample, even Ghost got emotional on 2006's Fishscale, complete with Ne-Yo on the chorus. Of course, he still talks about cutting off ring fingers in the lyrics. He took a much more humorous approach to these things a few years later with Fabolous on the excellent "Guest House."

4. Why?, "Good Friday"

Okay, these other dudes got emotional, but none of them can even approach the raw honesty of Yoni Wolf's epic exploration of the broken remains of a man after a breakup in Why?'s "Good Friday."

List continues on the next page.


3. Astronautalis, "Gaston Ave" As he often says at his shows, Astronautalis wrote this track immediately after simultaneously experiencing his first major heartbreak and discovering whiskey.

2. Jay Z, "Song Cry" With Kanye West doing your beats it's almost an inevitability that you're going to delve into something sensitive, and for one very brief, awesome moment even Hova let his guard down for a breakup anthem.

1. El-P, "The Overly Dramatic Truth" Known already for his stark lyrics, El-P lays out the truth of his own role in a bad breakup with his signature honesty.


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