100 Sad Rap Songs

Ray has been an online music writer for over four years. Having sung in multiple competitions as a youth, he has a passion for the art.

Sad rap songs contain lyrics that express emotion and confession, and they frequently blend hip-hop and rock music. Rappers, just like anyone else, suffer from sadness and sorrow. Some of them choose to express their feelings through music. Here are the 100 best sad rap songs about love and life to help you deal with your downcast mood and lift your spirits.

1. “U”

Artist: Kendrick Lamar

Album: To Pimp a Butterfly

Year Released: 2015

Facts About “U”

• Kendrick Lamar is undoubtedly one of the best rappers, creating the most powerful sad rap songs (2015) in history.
• During Kanye’s Yeezus tour, Kendrick encountered an event that led to the inspiration for the song.
• As Lamar himself revealed, “U” was one of the most challenging songs for him to compose. There are a lot of thorny issues in there, including his insecurities, selfishness, and letdowns.
• A sad rap song about life, this song is considered one of the best.

2. “Dance With the Devil”

Artist: Immortal Technique

Album: Revolutionary Vol. 1

Year Released: 2001

Facts About “Dance With the Devil”

• It is a song about a guy who decides to join a gang where he has to attack and rape a woman for initiation, only to realize it’s his mother when he looks into her face.
• Furthermore, the song emphasizes how crimes within your community can result in your demise and hurt your family members.
• As a result of the sampled piano beat from the 1970 track “Theme from Love Story,” the track has a dark, sinister, and menacing feel.

3. “4 Your Eyez Only”

Artist: J Cole

Album: 4 Your Eyez Only

Year Released: 2016

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Facts About “4 Your Eyez Only”

• Cole’s song, “4 Your Eyez Only,” is about his childhood friend James McMillan Jr., who died at the young age of 22.
• The song conveys love to his friend’s little girl and his little boy, as Cole repeatedly repeats “for your eyes” throughout the song.

4. “Keisha's Song”

Artist: Kendrick Lamar

Album: Section 80

Year Released: 2011

Facts About “Keisha’s Song”

• Kendrick tries to teach his little sister not to become a prostitute in this song, using a narrative tragedy as his example.
• “Keisha’s Song” is one of Kendrick Lamar’s favorite tracks from the album. Kendrick Lamar uses graphic language and profane lyrics to convey his message.
• In recognition of Kendrick Lamar’s status as king of rap, this song is one of the best sad rap songs that teach life lessons through music.

5. “Brenda’s Got a Baby”

Artist: 2Pac

Album: 2Pacalypse Now

Year Released: 1991

Facts About “Brenda’s Got a Baby”

• TwoPac’s song “Brenda’s Got a Baby” appears on his debut album 2Pacalypse Now.
• It tells the story of a 12-year-old named Brenda, who lives in a ghetto and cannot afford to raise a baby.
• Teen pregnancy and how it affects women and their families is the theme of the song.
• The song peaked at #7 on the US Billboard Hot Rap Songs and #23 on the US Billboard Hot R&B/Hip-Hop Songs in 1991.
• Due to its powerful message about life, the song became one of the most influential sad rap songs in history.

6. “Jocelyn Flores”

Artist: XXXTENTACION

Album: 17

Year Released: 2017

Facts About “Jocelyn Flores”

• American rapper XXXTentacion wrote and performed “Jocelyn Flores.”
• The song commemorates Jocelyn Amparo Flores, a 16-year-old girl from The Bronx and Cleveland, Ohio. While on vacation in Florida, she met XXXTentacion and later committed suicide.
• “Jocelyn Flores” entered the US Billboard Hot 100 at #31 and reached #19 just after the artist’s death.
• Producer Potsu created the song based on his song “I’m Closing My Eyes,” which features vocals by Shiloh Dynasty.

7. “Sing About Me, Dying of Thirst”

Artist: Kendrick Lamar

Album: Good Kid, MAAD. City

Year Released: 2012

Facts About “Sing About Me, Dying of Thirst”

• Kendrick Lamar’s song “Sing About Me, I’m Dying of Thirst” appears on his major-label debut studio album Good Kid, MAAD City.
• The song has an emotional lyricism and an innovative approach to rapping; the song became one of Lamar’s most famous sad rap songs to listen to and play.
• The song has two parts. First, it tells the story of Kendrick’s (Dave) friend who died from gun violence, as his brother is only interested in getting revenge. The second part tells about the struggles of a young girl who turns to prostitution to survive.
• An episode of Grey’s Anatomy with the title “Man on the Moon” featured the song.

8. “You Never Know”

Artist: Immortal Technique

Album: Revolutionary Vo. 2

Year Released: 2003

Facts About “You Never Know”

• The technique features a much more emotional and personal rap song on Revolutionary Vol. 2 than on other releases, detailing an accurate account of his experiences with love and relationships.
• The song is a torrid love story, viewing the ‘urban’ or ‘inner-city’ world.
• Critics claim that this could be one of the saddest rap songs they’ve heard in ages.

9. “All That I Got Is You”

Artist: Ghostface Killah ft. Mary J. Blige

Album: Ironman

Year Released: 1996

Facts About “All That I Got Is You”

• Ghostface Killah released “All That I Got Is You” as the lead single from his solo debut album Ironman.
• “All That I Got Is You” is one of the sad rap songs about love for mothers. Ghostface wrote the song as a tribute to his mother, with lyrics that depict both the harsh life the two lived during Ghostface’s childhood and praise his mother’s ability to teach him even in their difficult circumstances.
• A survey by About.com ranked the song at 87th on its Top 100 Rap Songs list.

10. “Beautiful”

Artist: Eminem

Album: Relapse

Year Released: 2009

Facts About “Beautiful”

• In August 2009, Eminem released the fourth and final single “Beautiful” from his sixth studio album, Relapse.
• He started writing the song in rehab in 2005, but he would not finish it until he got clean in 2010, when he added a third verse and released the track on the album.
• “Beautiful” is one of the heartfelt slow, sad rap songs that talks about how Eminem feels about how his life has been going.
• The song debuted at #17 on the Billboard Hot 100 in the US and made it to BBC Radio 1’s A-List.

11. “When I’m Gone”

Artist: Eminem

Album: Curtain Call: The Hits

Year Released: 2005

Facts About “When I’m Gone”

• “When I’m Gone” is part of Eminem’s most fantastic hit album, Curtain Call: The Hits (2005).
• Music critics gave the song mixed to negative reviews, but it charted at #8 on the Billboard Hot 100.
• It’s one of the saddest rap songs about a celebrity father constantly neglecting his family to be famous.
• Eminem uses this song to tell his fans that he fears losing his daughter Hailie and wants to have an everyday life with her and his wife.

12. “Suicidal Thoughts”

Artist: The Notorious B.I.G.

Album: Ready to Die

Year Released: 1984

Facts About “Suicidal Thoughts”

• In collaboration with the producer Lord Finesse, a rapper better known to old school audiences as the Notorious BIG, BIG wrote this song.
• Suicidal Thoughts is the title track from The Notorious BIG’s first studio album, Ready to Die.
• It is one of the most depressing rap songs that separates Biggie from other gangsta rappers today.
• In this song, The Notorious BIG contemplates and eventually commits suicide.

13. “Six Feet Deep”

Artist: Geto Boys

Album: Till Death Do Us Part

Year Released: 1993

Facts About “Six Feet Deep”

• Geto Boys perform “Six Feet Deep” from their album Greatest Hits, released in 2013.
• There is a lot of emotion in this song, reflecting how it feels to see one’s friends get shot.

14. “Slippin”

Artist: DMX

Album: Flesh of My Flesh, Blood of My Blood

Year Released: 1998

Facts About “Slippin”

• DMX released “Slippin’” as the first single from his second studio album, Flesh of My Flesh, Blood of My Blood.
• The music video provides a glimpse into DMX’s youth.
• DMX wrote this song to express what life is like on the streets and how you can overcome life with drugs if you give it all.
• As the song begins, the speaker describes his problems with his mother, which is why he runs away from home.

15. “Song Cry”

Artist: Jay-Z

Album: The Blueprint

Year Released: 2002

Facts About “Song Cry”

• “Song Cry” is an emotional ballad in which Jay describes the pain of his long-term relationship ending due to his philandering and busy schedule.
• “Song Cry” won the Grammy for best male rap solo performance, losing to Nelly’s “Hot in Here.”
• It is one of the slow, sad rap songs from Jay-Z where he laments the break-up of an earlier relationship due to his infidelity and neglect.

16. “The Last Emperor and Too Poetic”

Artist: One Life

Album: Music, Magic, Myth

Year Released: 2003

Facts About “The Last Emperor and Too Poetic”

• At the beginning of the verse, Jamal Gray, the Last Emperor, expresses his shock at learning that Derek has passed away.
• The singer refers to Poetic, also known as Grim Reaper, and died from colon cancer shortly after making this song.

17. “Stan”

Artist: Eminem

Album: The Marshall Mathers LP

Year Released: 2000

Facts About “Stan”

• Eminem’s song “Stan” features vocal samples from Dido’s “Thank You,” written by the British singer.
• It tells the story of an obsessed fan whose hero-worship and probable mental illness caused him to die young.
• Everyone considers “Stan” one of his signature songs and one of Eminem’s best sad rap songs.

18. “Life’s a Mess”

Artist: Juice Wrld and Halsey

Album: Legends Never Die

Year Released: 2020

Facts About “Life’s a Mess”

• Juice Wrld and Halsey collaborated on the song “Life’s a Mess.” Previously, the two artists collaborated on Halsey’s chart-topping single “Without Me.”
• Clever released what would be the original version of the song featuring Juice Wrld on March 5, 2021 (before Halsey released her album version in July 2020), titled “Life’s a Mess II.”
• Juice and Halsey convey their life’s struggles on the track while expressing appreciation to their desired partners.

19. “Robbery”

Artist: Juice Wrld

Album: Death Race for Love

Year Released: 2019

Facts About “Robbery”

• On February 13, 2019, Juice Wrld released the song “Robbery” as the second single from his sophomore album Death Race for Love via Grade A Productions.
• Described as a sad rap song about a woman stealing Juice’s heart, “Robbery” is an emotional song about separation.
• One of Juice Wrld’s somber “let go” sad rap songs, “Robbery,” tells the story of a broken heart through the frequent themes of love and heartbreak showcased in the rapper’s music.

20. “Kim”

Artist: Eminem

Album: The Marshall Mathers LP

Year Released: 2000

Facts About “Kim”

• “Kim” is one of the sad rap songs about a life full of hatred popularized by Eminem.
• Throughout the song, Eminem imitates Kim Mathers’ voice and describes his anger and hatred toward her, ending by explaining how he killed Kim before putting her in the trunk of his car.
• In late 1998, after completing The Slim Shady LP, Eminem began working on the new album’s first track, “Kim.”

21. “Calling My Phone”

Artist: Lil Tjay, 6lack

Album: Destined 2 Win

Year Released: 2021

Facts About “Calling My Phone”

• Lil Tjay and 6lack released “Calling My Phone” on February 12, 2021, through Columbia and Sony.
• Generally, the lovelorn song refers to the desire to escape the grip of an ex-lover.
• According to Billboard, “Calling My Phone” debuted at #3 on the Hot 100 chart, making Lil Tjay and 6lack’s highest-charting single.

22. “I Fall Apart”

Artist: Post Malone

Album: Stoney

Year Released: 2016

Facts About “I Fall Apart”

• Post Malone wrote this song as a response to a break-up. In this break-up, it is evident that Austin is very close to his ex-partner, as obvious in the lyrics.
• In the track, Post Malone comes off as a hurting man hurt by someone he truly loved unconditionally.
• “I Fall Apart” is one of the most depressing and sad rap songs about love.

23. "Colored Dreams"

Artist: Reason

Album: There You Have It

Year Released: 2018

Facts About “Colored Dreams”

• The record “Colored Dreams” is written from the perspective of a prisoner serving a murder sentence.
• The album is a cold-eyed examination of street life, cementing Reason’s place on one of the best rap rosters.
• I found “Colored Dreams” strikingly similar to HBO’s Barry, which looks at how a murder affects the entire ecosystems of those around and behind victimized people.

24. "Hellboy"

Artist: Lil Peep

Album: Hellboy

Year Released: 2016

Facts About “Hellboy”

• The Hellboy mixtape expresses numerous suicidal declarations, drug usage, and moments of enjoyment and delight.
• Hellboy is Lil Peep’s fifth and final mixtape, released on September 25, 2016.

25. “I’ll Be Missing You”

Artist: Puff Daddy and Faith Evans featuring 112

Album: No Way Out

Year Released:1997

Facts About “I’ll Be Missing You”

• Faith Evans and Puff Daddy perform the song “I’ll Be Missing You” in memory of Christopher “The Notorious BIG” Wallace, a fellow Bad Boy Records artist.
• This song won the Grammy Award for Best Rap Performance by a Duo or Group at the 40th Annual Grammy Awards.
• With an interpolated chorus sung by Evans and an improvised rhythm, “I’ll Be Missing You” samples the Police’s 1983 hit song “Every Breath You Take.”

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This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2021 Ray