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Top 10 Hip Hop Heartbreak Anthems

Submitted by on February 14, 2010 – 7:19 pm8 Comments

When we think of hip hop, we generally think of pimps, players, and smooth operators. Of course, those illusions are a far cry from actual life and the emotions that we all go through from time to time. For all those who are single on Valentine’s Day (like me), here’s a list of songs inspired by unrequited love and/or breakups (in chronological order).

“Roxanne, Roxanne”


This one is for the guys whose lines just weren’t good enough. All three rappers – Kangol Kid, Educated Rapper, and Doctor Ice – tried to get at Ms. Roxanne, but she just didn’t want to hear it. The guys seem a little bitter in the song, as they portray Roxanne as stuck up, cruel, and insensitive. Of course, the bitterness had just begun as the song spawned countless response records. The original as well as the responses are collectively known as the Roxanne Wars. It would seem, then, that Roxanne is hip hop’s very own Helen of Troy. Take out your frustrations on the one who got away with UTFO‘s “Roxanne, Roxanne.”

“Teenage Love”

Slick Rick

As we think about our first experiences in relationships, we undoubtedly have flashbacks about our Wonder Years, school dances, catching movies, buying gifts, etc. Slick Rick masterfully captures the nostalgia of the unbelievable highs and the inevitably crushing lows which come with teen relationships via this classic record. What truly separates him, though, is that he does so in a way that both sexes can understand. This Valentine’s Day, let Slick Rick take you back to the good ol’ days with “Teenage Love.”

“Just A Friend”

Biz Markie

Talented beatboxer and rapper Biz Markie wound up hurting so bad at the hands of his girl that he chose to sing. Decades later, we still love him for it. You know how the story goes: Boy meets girl, boy likes girl, boy gets cheated on by girl with a guy she says is “just a friend.” I’m not exactly sure how sorry we should feel for ol’ Biz though. He can’t even remember her name and refers to her as “blah-blah-blah” the whole song. “Just A Friend” by Biz Markie definitely makes this list because while it’s a heart-breaker, it’s done humorously. After all, even the smoothest fellas get cheated on every once in a while. Here’s to laughin’ it off and keepin’ it movin’.

“Bonita Applebum”

A Tribe Called Quest

Of course, this classic record by A Tribe Called Quest chronicles a man’s attempts to pick up the object of his affection. While the conclusion of the song doesn’t offer many clues as to whether or not Q-Tip was successful, the music video makes it pretty obvious. I blame the ‘crazy prophylactics’ line for keeping Ms. Applebum from putting the young MC on. Fellas, we’ve got to do better. In the meantime, travel down memory lane with the humorous and timeless “Bonita Applebum.”

“Da Art of Storytellin’” ft. Slick Rick


One of the greatest duos in hip hop hands down, Big Boi and Andre 3000 have a great deal of stories to tell about hustlers, players, Cadillacs, and the like. It came as quite a surprise when the duo joined with Rick the Ruler to tell about loves they had lost. 3000′s verse was by far the most memorable, as he tells of a girl he had feelings for growing up. He hoped to see her as his popularity increased, but her hard life got the best of her before he ever got the chance. Sad times, great song.

“Song Cry”


Even the man many consider the King of New York has had his share of heartbreak.  What makes Jay-Z‘s take on the subject so unique, though, is his willingness to admit that losing his love was mostly his fault. That plus the creative spin that he put on the bravado and stoicism that keep masculine men (like a certain well-spoken Genius) from crying during his chorus make the song nearly unforgettable. “I can’t see ‘em comin’ down my eyes, so I gotta make this song cry.” Let Mr. Knowles-Carter’s “Song Cry” shed your tears if you’re too hard to let ‘em go.

“I Need A Girl (Pt. 1)”  ft. Usher and Loon


Shortly following his high-publicity romance with Jennifer Lopez (which nearly ended in a blaze of glory), a newly-acquitted Diddy was back in the studio and ready to reflect on lessons he had learned by his failed relationship. With a mid-tempo beat designed for us to grind, and Usher on the hook, the stage was set for all to hear about Mrs. Marc Anthony, who Diddy describes in the song as “the one that I will always miss.” I will certainly have Diddy’s “I Need A Girl” on repeat tonight. I can relate.


Outkast returns with a more humorous take on unrequited love with “Roses.” Largely dominated by Andre 3000 (who, of course, was more of a pop/soul singer at this point than a rapper) the song ends with a verse by Daddy Fat Sacks as well. This one’s all about Caroline, a pretentious and shallow beauty who can’t see past a man’s bank account to his true worth. She’s so cruel that Andre ends up famously hoping she crashes into a ditch (just playing, of course). If you’re bitter in an upbeat kind of way about a gold-digger who’s done you wrong, Outkast’s “Roses” is your song.


Kanye West

Honestly, I could’ve listed the entire 808s and Heartbreak album here. However, because I’m all about consistency, I’ll stick to one song. On “Heartless,” Kanye West comes closer to actual rapping than on any other record on the album. This one’s a breakup album about a woman who is cold, cruel, and… well, heartless. Martin Louis The King, Jr. does a pretty good job of summing up the deterioration of a relationship. “You run and tell your friends that you’re lea-vin’ me, they say that they don’t see what you see in me…” Of course, Mr. West gets the last laugh with the lines that follow. If your ex is cold enough to put the recent snowstorms across America to shame, this is your jam.

“Say Something”  ft. Drake


SideNote: This is supposed to be a Timbaland record, but let’s be honest. Timbo has, of late, made a living out of producing songs where other artists do most of the vocal work and proceeding to call them his own. Can’t hustle The Genius, just sayin’…

Say what you will, but I think Drake may be at his best when he’s having his emo moments.  Drizzy recently revealed to Complex Magazine that most of his freakishly successful mixtape, So Far Gone, was inspired by his experiences with his ex. One listen to this record will most likely bring one to a conclusion similar to the one I drew: he’s not done venting yet. The man talks about his pain, anguish, and the fact that he still wants her attention and to know that he matters to her. If you’re in a similar situation, allow Drake to “Say Something” to you.

Your thoughts?

Main Image: Ms. Notoriously Addictive

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