15 Best Sad Rap Songs That Will Leave You in Tears

Are you wondering what the Best Sad Rap Songs are?

Rap music has always been a powerful medium of self-expression, with artists pouring their hearts and souls into their lyrics. While rap is commonly associated with braggadocio and confidence, a whole other side to the genre produces some of the most heart-wrenching and poignant songs out there. 

In this post, we’ll be deeply diving into the 15 best sad rap songs guaranteed to hit you right in the feels.

Best Sad Rap Songs

1. “Yesterday” by Atmosphere:

This classic track by Minneapolis-based duo Atmosphere is a haunting meditation on regret and self-loathing. MC Slug’s introspective lyrics over Ant’s melancholy production make this song a must-listen for anyone feeling the blues.

2. “Love” by Kendrick Lamar:

One of the standout tracks from Kendrick Lamar’s critically acclaimed second album, To Pimp A Butterfly, “Love,” is a painful reflection on the difficulties of maintaining a healthy relationship. Featuring guest vocals from singer-songwriter Zacari, this song is a raw and emotional portrait of love’s highs and lows.

3. “Stan” by Eminem:

This iconic song by Eminem is a masterful examination of obsession and estrangement. Told from the perspective of a deranged fan named Stan, the song builds to a stunning, tragic, and cathartic climax.

4. “Sad!” by XXXTENTACION:

One of the most controversial and influential figures in modern rap, XXXTENTACION’s music was often characterized by his vulnerability and raw emotion. “Sad!” is a prime example, with XXXTENTACION laying bare his deepest regrets and fears over haunting guitar arpeggios.

5. “Summertime Sadness” (Remix) by Lana Del Rey ft. ASAP Rocky:

While the original version of this song by Lana Del Rey is already a masterpiece of melancholy, the remix featuring ASAP Rocky adds a whole new layer of sadness to the proceedings. ASAP’s verses paint a vivid picture of heartbreak and loss, making this remix an essential listen for any fan of sad rap.

6. “All of the Lights” by Kanye West ft. Rihanna and Kid Cudi:

While not strictly a sad song, “All of the Lights” still conveys a sense of existential despair through its bombastic production and haunting chorus. Featuring guest vocals from Rihanna and Kid Cudi, this song is a tour-de-force of emotion and sound.

7. “Dance With the Devil” by Immortal Technique:

One of rap’s most visceral and disturbing songs, “Dance With the Devil,” tells the story of a young man’s descent into depravity and violence. With its graphic depictions of rape and murder, this song is not for the faint of heart, but its message about the cyclical nature of violence is an important one to hear.

8. “The Message” by Nas:

While not specifically a sad song, “The Message” still conveys a sense of disillusionment and despair through its vivid depiction of life in the ghetto. Nas’s sharp lyrics and D.J. Premier’s haunting production make this song an unforgettable portrait of urban decay.

“How to Love” by Lil Wayne:

One of the most unexpected songs in Lil Wayne’s catalog, “How to Love,” is a heartbreaking rumination on regret and lost love. With its acoustic guitar-driven production and Lil Wayne’s introspective lyrics, this song is a departure from the rapper’s usual braggadocio but no less affecting for it.

9. “Sing About Me; I’m Dying of Thirst” by Kendrick Lamar:

Another standout track from To Pimp A Butterfly, “Sing About Me,” is a sprawling epic about the struggles of life in Compton. Featuring a haunting hook by vocalist Anna Wise, this song is a masterclass in storytelling and emotion.

10. “Suicidal Thoughts” by The Notorious B.I.G.:

The final track on The Notorious B.I.G.’s classic debut album Ready to Die, “Suicidal Thoughts,” is a heartbreaking meditation on the rapper’s mortality. It’s a chilling reminder that even the most seemingly invincible artists can be vulnerable and fragile.

11. “Mockingbird” by Eminem:

Another standout track from Eminem’s oeuvre, “Mockingbird,” is a touching tribute to his daughter Hailie. With its tender production and heartfelt lyrics, this song is a reminder that under the guise of the “angry rapper,” Eminem is capable of genuine vulnerability and emotion.

12. “The Book of Soul” by Ab-Soul:

This song by T.D.E. rapper Ab-Soul is a poignant portrait of grief and loss. Dedicated to his late girlfriend, Alori Joh, the piece deftly weaves memories and emotions into a powerful tribute to a life lost too soon.

13. “Nate” by Vince Staples:

One of the standout tracks from Vince Staples’ great debut album Summertime ’06, “Nate,” is a harrowing depiction of gang violence and its repercussions. With its sparse production and Vince’s intelligent lyrics, the song is a sobering reminder of the human cost of street life.

14. “Self Control” by Frank Ocean:

One of the most heartbreaking songs in recent memory, “Self Control” by Frank Ocean, is a devastating portrait of unrequited love. With its sparse, haunting production and Frank’s yearning vocals, the song perfectly captures the feeling of wanting someone who doesn’t want you back.

Conclusion: Best Sad Rap Songs

It’s easy to dismiss rap as a genre of aggression and bravado, but as we’ve seen in this list, there’s a whole other side to rap music that is just as powerful and affecting. 

From heartbreak to loss to regret, these 15 sad rap songs are a testament to the genre’s ability to tap into the full range of human emotions. So whether you’re feeling down or just in the mood for some raw and honest music, we highly recommend listening to these songs.

Frequently Ask Questions

Who is the saddest rapper?

The saddest rapper is generally regarded as being Eminem. His songs often delve into his depression, loneliness, and struggle with addiction. Other rappers who make sad music include Lil Wayne, The Notorious B.I.G., Kendrick Lamar, and Vince Staples.

What is the saddest rap song ever?

The saddest rap song ever is a subjective matter. Still, some contenders include “Sing About Me, I’m Dying of Thirst” by Kendrick Lamar, “Suicidal Thoughts” by The Notorious B.I.G., and “Mockingbird” by Eminem.

What rap songs make you cry?

Any number of rap songs can evoke an emotional response in listeners, but some of the saddest include “How to Love” by Lil Wayne, “Book of Soul” by Ab-Soul, and “Self Control” by Frank Ocean. These songs are all powerful portraits of loss, grief, and regret that can bring even the most stoic listeners to tears.

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