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10 Saddest Rap Songs About Love of All Time

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Don’t sleep on rappers being in tune with their singing and with their emotions. Like rock, pop, and country, the lyrical poetry of rap has been demonstratively complex and capable of telling stories. 

Eminem’s “Stan” has become as important as a cultural touchpoint, as it was a lesson on intense fandom. So it should be no surprise that a rap song could delve deep into the sadness of love. 

So, let’s delve into the saddest rap songs about love!

1. Marvin’s Room – Drake

Many people can relate to Drake and his song “Marvin’s Room.” Reportedly named after the recording studio once owned by legend Marvin Gaye, “Marvin’s Room” off Drake’s second album Take Care, tells the story of Drake drunk-dialing an ex. 

The music is low-key and matches the lyrical story well. During the call, Drake continues his affection for the woman on the phone, talks about partying too hard, women he’s slept with, and his desire to get her back. 

But, much like the real Gaye’s life story, this one doesn’t end well either.

2. Sunday – Earl Sweatshirt

When you consider this track is from Earl Sweatshirt’s debut album, you almost forget that he was a kid when it was released. Born in 1994, Earl released this album in 2013.

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Filled with a ridiculous group of A-list guest appearances, it’s “Sunday” that feels sad. Featuring an uncharacteristically rapping Frank Ocean, “Sunday” is about both men reflecting on their past (including Ocean referring to his brawl with Chris Brown). 

3. L.E.S. – Childish Gambino

Childish Gambino may not drop the music frequently, but when he does, watch out – he’s coming in hot with a deeply thought-provoking track. 

Childish Gambino dropped his debut album Camp in 2011. Tracks like “Bonfire” and “Heartbeat” were the big hitters, but it was “L.E.S.” that dug into the heartstrings.

Known for mixing pop-culture references within quick lyrical rhymes, Childish Gambino raps about the time with his girl, making out in the bathroom, and self-criticizing the failure of nothing more.

4. Love Me Not – J. Cole

Released in 2010 on J. Cole’s third mixtape, Friday Night Lights, “Love Me Not” takes its cue from the classic pedal-plucking antics of love-lorn individuals. Much like the others on this list, this song sweeps amidst the love that is lost. 

The song goes back and forth between sadness and anger, the feelings all too familiar for those at the end of a relationship. 

5. Doing It Wrong – Drake

If you thought that Drake only waxed poetic on one track, you’re sadly mistaken by any of the saddest rap songs about love. Also off his album Take Care, “Doing It Wrong” may not carry the gravitas of “Marvin’s Room” but it can hold its own in sadness.

Lyrics like “Cause you’ll say you love me, and I’ll end up lying/ And say I love you, too/ But I need someone different” hint at the “it’s not me, it’s you” relationship ender. 

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6. Song Cry – Jay-Z

This song is now old enough to drown itself in a drink. The last single off the landmark The Blueprint, “Song Cry” tells the story of Jay-Z sabotaging a past relationship because of his neglect and infidelity. 

Since Jay-Z is too prideful to show his sadness, he makes “this song cry” to compensate. 

7. Blame Game – Kanye West

Kanye is about as complicated publicly as his very public love life. “Blame Game” off his critically adored My Beautiful Dark Twisted Fantasy, tells the aftermath of a deeply dysfunctional relationship and the anger of knowing the woman is with another man. 

The song ends with Yeezy hearing a conversation between the woman and the new man, cutting Yeezy apart after he laid the tracks physically that this new man is experiencing. 

Hard not to imagine some parallels between this and the new public battles with Kim and Pete. 

8. IFHY – Tyler, The Creator

This one-off Tyler, The Creator’s Wolf, is arguably the angriest sad rap song on this list. Guided by Pharrell, it echoes some classic elements from The Neptunes melodically. Tyler swings hard with a love/ hate balance. 

“Even though I hate you/ I still love you” and “I love you so much that my heart stops beating when you leave” are great examples of the scales imbalanced. 

9. Unconditional Love – 2Pac

This posthumously released song was the lead-off for 2Pac’s Greatest Hits album. 2Pac wrote this song for none other than MC Hammer. 2Pac recorded a demo of the song before handing it over, and this demo is what ended up being released. 

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If you remove the idea of 2Pac singing it and place it in the guise of MC Hammer, it feels like a different song, but when this original demo version is played, it feels like a sad reflection on a life cut short, but remaining hopeful and focused on unconditional love.

10. Nothing Lasts Forever – J. Cole

Repeat artist again, but a worthy last addition to the list. J. Cole is one to share his soul. “Nothing Lasts Forever” is a track not included on his debut album Cole World: The Sideline Story, which was released in 2011. 

Another love song, another reflection on lost love. Lyrics like “We went from friends to somethin’ much more” and “We break each other’s hearts, so maybe it’s for the better” paint the picture, and end with a bit of introspection “and nothin’ lasts forever, least we got these memories.”