The Best 250 Sad Rap Songs | Our Playlist of Depressing Rap Songs

Welcome to our review of the best 250 sad rap songs.

This collection pays homage to the late rappers who played an instrumental role in shaping and popularizing the sub-genre of sad rap. Artists like Juice WRLD, XXXTENTACION, Lil Peep, and Mac Miller used their personal experiences to create emotionally-charged music that resonated deeply with fans.

In this blog post, we'll take you on a journey through the most heart-wrenching and soulful songs in the genre, exploring the raw emotions, and poetic lyricism that has made sad rap a beloved staple of the hip-hop world.

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To listen to the full list of the 250 best sad rap songs, click here.

Or, read on to learn more about some of the most depressing rap songs around!

45 of the Saddest Rap Songs

Now, let's provide further analysis for some of the best depressing rap songs.

1. the remedy for a broken heart (why am I so in love) by XXXTENTACION

"the remedy for a broken heart (why am I so in love)" by XXXTENTACION is a melancholic ballad that captures the singer's emotions of heartbreak and betrayal.

The song features a simple guitar melody and the raw, vulnerable vocals of XXXTENTACION. The lyrics are introspective, with XXXTENTACION questioning why he's so in love with someone who has hurt him.

2. Welcome To Heartbreak by Kanye West & Kid Cudi

"Welcome To Heartbreak" by Kanye West & Kid Cudi is a reflective track that touches on the isolating nature of fame and success. The song features heavily auto-tuned vocals and a somber beat, with Kanye West and Kid Cudi trading verses about the pitfalls of fame and their personal struggles.

The chorus, which features a sample from a song by Coldplay, emphasizes the emotional turmoil that comes with being in the public eye.

3. Lucid Dreams by Juice WRLD

"Lucid Dreams" by Juice WRLD is a haunting track that explores themes of heartbreak, addiction, and depression. Lucid Dreams is one of the most popular sad hip hop songs, with the Lyrical Lemonade Music Video sitting with over 1 billion views.

The song features a melancholic piano melody and Juice WRLD's emotive vocals, with lyrics that express his desire to escape his pain through his dreams. The chorus, which features a sample from Sting's "Shape of My Heart," is a poignant reflection on the nature of love and loss.

4. Mirror by Lil Wayne & Bruno Mars

"Mirror" by Lil Wayne & Bruno Mars is a reflective track that touches on themes of self-doubt and insecurity. The song features Lil Wayne's introspective verses and Bruno Mars' soaring chorus, with lyrics that emphasize the need to find inner strength and self-acceptance. The music video, which features Lil Wayne and Bruno Mars looking at themselves in the mirror, adds to the song's introspective nature.

5. Teenage Fever by Drake

"Teenage Fever" by Drake is a wistful track that touches on themes of lost love and nostalgia. The song features a sample from Jennifer Lopez's "If You Had My Love" and Drake's emotive vocals, with lyrics that reflect on a past relationship and the memories that still linger.

The song's dreamy production and Drake's introspective verses create a melancholic atmosphere that perfectly captures the song's themes.

6. Falling Down by Lil Peep & XXXTENTACION

This song was released posthumously by Lil Peep and XXXTENTACION, two young and talented artists who passed away before their time. The lyrics are introspective and discuss their struggles with mental health, drug addiction, and fame.

The haunting melody and emotive lyrics make this song a poignant tribute to these artists, and is certainly one of the saddest hip hop songs to date.

7. Apologize by Timbaland & OneRepublic

This song explores the theme of regret and the desire to make amends. The lyrics express the pain and sadness of a failed relationship and the hope that a heartfelt apology might bring closure. The chorus is particularly powerful, with the repetition of "it's too late to apologize" emphasizing the finality of the situation.

8. Highs and Lows by Lil Skies

In this sad rap song, Lil Skies reflects on the ups and downs of his life, from his struggles with addiction and relationships to his newfound success in the music industry. The lyrics are honest and raw, and Lil Skies' delivery is emotionally charged, conveying the highs and lows of his experiences. See what I did there?

9. Conversations by Juice WRLD

This song is a deeply introspective exploration of Juice WRLD's thoughts and feelings, delving into his struggles with mental health and addiction. The lyrics are candid and honest, and Juice WRLD's unique flow and delivery make this song stand out.

The haunting melody adds to the overall mood of melancholy and introspection, and is in my opinion one of his best sad rap songs.

10. Marvins Room by Drake

This song is a heart-wrenching depiction of a man's drunken late-night phone call to an ex-lover. The lyrics are brutally honest and emotionally raw, and Drake's delivery is powerful, conveying the desperation and regret of the protagonist.

The use of a sample from the song "I'll Take Care of You" by Gil Scott-Heron and Jamie xx adds to the overall mood of sadness and longing.

11. Stan by Eminem

"Stan" by Eminem is a haunting portrayal of an obsessed fan and his unhealthy attachment to Eminem. The song features a sample from Dido's "Thank You" which adds to the melancholic vibe of the track.

Eminem's lyrics depict the fan's descent into madness and ultimately his tragic end, making it one of the most emotional and powerful songs in rap history.

12. Molly by Lil Dicky (feat. Brendon Urie)

One of the most depressing rap songs, Molly, is a deeply introspective track that explores Lil Dicky's struggles with anxiety and depression. The song features an emotional chorus from Brendon Urie of Panic! at the Disco, who adds to the overall mood of the song. Lil Dicky's lyrics are honest and raw, and the vulnerability he shows is both relatable and heart-wrenching.

13. Autumn Leaves by Chris Brown & Kendrick Lamar

"Autumn Leaves" by Chris Brown & Kendrick Lamar is a melancholic and introspective song that explores the themes of loss and regret. The song features an atmospheric beat and a beautiful piano melody, which sets the tone for the introspective lyrics.

Kendrick Lamar's verse is particularly poignant, as he reflects on the pain of losing loved ones and the importance of cherishing the moments we have with them.

14. Coming Home by Diddy & Skylar Grey

"Coming Home" by Diddy & Skylar Grey is an emotional ballad that explores the feeling of longing for a loved one. The song features a soaring chorus from Skylar Grey and heartfelt verses from Diddy, which add to the overall emotional impact of the track.

The lyrics are relatable and universal, and the song's message of love and longing has resonated with audiences around the world.

15. Rich & Sad by Post Malone

"Rich & Sad" by Post Malone is a somber track that explores the struggles of fame and fortune. The song features a slow, brooding beat and Post Malone's signature autotuned vocals, which give the song a melancholic vibe. The lyrics depict the emptiness and loneliness that can come with wealth and success, making it a powerful and emotional track.

16. All Girls Are The Same by Juice WRLD

In this song, Juice WRLD talks about heartbreak and his inability to find a girl who truly understands him. He explains how he's been hurt by different girls in the past and how he's come to the conclusion that all girls are the same. The lyrics are emotional and relatable, which is why this song has resonated with so many fans. This is one of those sad rap songs that will continue to stand the test of time.

17. changes by XXXTENTACION

In "changes," XXXTENTACION reflects on his past mistakes and how he's changed as a person. He talks about the difficulties of growing up and the struggles he's faced along the way.

This is one of those depressing hip hop tracks that has a melancholic tone and a powerful message about the importance of personal growth and reflection.

18. Never Forget You by Lupe Fiasco & John Legend

This song is a beautiful tribute to loved ones who have passed away. Lupe Fiasco and John Legend's vocals complement each other perfectly, creating a powerful and emotional song. The lyrics are touching and heartfelt, reminding us to cherish the memories of those who are no longer with us.

19. Heartbeat by Childish Gambino

In "Heartbeat," Childish Gambino talks about the ups and downs of a romantic relationship. He reflects on the moments of love and the moments of heartbreak, all while showcasing his signature clever wordplay and metaphors. The song is both relatable and catchy, making it a fan favorite.

20. I Fall Apart by Post Malone

In this song, Post Malone talks about the pain of heartbreak and how it affects him.

He discusses his inability to move on from a past relationship and how he's struggling to deal with the emotional turmoil. The song's powerful chorus and raw emotion have made it a hit among fans, who relate to its themes of heartbreak and vulnerability.

21. I'm Sorry by Joyner Lucas

Joyner Lucas’ “I’m Sorry” is a gut-wrenching apology to a friend who committed suicide. The track delves deep into themes of guilt, loss, and self-reflection as Lucas tries to come to terms with his role in his friend’s death. The song's haunting lyrics, combined with Lucas' emotional delivery, make it a powerful tribute to the pain and complexity of loss.

22. 1-800-273-8255 by Logic, Alessia Cara & Khalid

“1-800-273-8255” is one of the most emotional rap songs, touching on the heavy topic suicide prevention, named after the US National Suicide Prevention Lifeline number.

The track's lyrics speak directly to those who may be struggling with suicidal thoughts, offering them hope and a way out. The inclusion of Alessia Cara and Khalid on the track adds to the song's emotional impact, creating a powerful anthem for anyone who's ever felt alone.

23. See You Again by Wiz Khalifa (feat. Charlie Puth)

“See You Again” is a moving tribute to Paul Walker, the late actor who starred in the "Fast and Furious" film franchise. Wiz Khalifa's lyrics celebrate the life of his friend, while Charlie Puth's soulful chorus offers a message of hope for those left behind.

The song's stirring melody and heartfelt lyrics have made it a classic, resonating with audiences around the world.

24. If You Want Love by NF

NF’s “If You Want Love” is a touching song that explores the complexities of love and relationships. The track's deep lyrics, coupled with NF's emotive delivery, paint a picture of the artist's struggles with intimacy and trust. The song's message is ultimately one of hope, reminding listeners that love is possible, even in the face of pain and disappointment.

25. How To Love by Lil Wayne

“How to Love” by Lil Wayne is a poignant and reflective track that delves deep into the complexities of love and relationships. The song's mellow melody and Lil Wayne's soulful delivery make it a standout in his repertoire, as the rapper eschews his usual bravado for a more introspective approach.

The lyrics explore the complexities of love, offering insight and understanding to anyone who's ever struggled to navigate the treacherous waters of the heart.

26. Me, Myself & I by G-Eazy & Bebe Rexha

This song is an upbeat, catchy tune that tackles the topic of independence and self-empowerment. The lyrics speak to the idea that it's okay to be alone and that finding happiness within oneself is key to a fulfilling life. The chorus, sung by Rexha, is particularly memorable, with her powerful voice urging listeners to focus on themselves and their own well-being.

27. Dark Queen by Lil Uzi Vert

"Dark Queen" by Lil Uzi Vert is a melancholic yet introspective track that explores the aftermath of a failed relationship. The song's lyrics describe the rapper's feelings of loss and loneliness, as he struggles to move on from a past love.

The track's production is haunting and moody, with eerie synths and hard-hitting drums adding to the song's overall sense of melancholy.

28. Broken by Lund

"Broken" by Lund is a slow-burning, emotional ballad that speaks to the pain and heartbreak of a failed relationship. The song's sparse production, consisting of little more than a guitar and Lund's raw vocals, allows the lyrics to take center stage.

Lund's lyrics are poignant and introspective, with his words painting a vivid picture of a broken heart struggling to heal.

29. Taking A Walk by Trippie Redd

"Taking A Walk" by Trippie Redd is a reflective sad rap song that explores the rapper's journey through life and the lessons he's learned along the way.

The song's lyrics are introspective and thoughtful, with Trippie Redd reflecting on his past mistakes and vowing to learn from them. The hip hop track's production is atmospheric and moody, with dreamy synths and a laid-back beat adding to its introspective vibe.

30. Scared of Love by Juice WRLD

"Scared of Love" by Juice WRLD is a poignant track that delves into the artist's fears and insecurities around love and relationships. The song's lyrics speak to the rapper's anxieties around opening up to others and being vulnerable, with Juice WRLD's words painting a vivid picture of a young man grappling with his emotions.

The track's production is minimal and understated, with a simple piano melody and atmospheric synths adding to its emotional impact.

31. Scared by Russ

In "Scared," Russ discusses his insecurities and fears of failure, reflecting on the pressure he feels as an artist. The sad rap song explores themes of anxiety and self-doubt and the struggles that come with pursuing your dreams.

Through introspective lyrics and a heartfelt delivery, Russ reminds us that it's okay to feel scared sometimes and that perseverance and self-belief are essential to overcoming our fears.

32. emotions by iann dior

"emotions" by iann dior is a sad rap song that explores the emotional turmoil that can come with love and heartbreak. The song captures the feeling of being overwhelmed by emotions and the confusion that can arise when trying to navigate relationships.

With raw lyrics and a soulful delivery, iann dior shows the vulnerability and complexity that comes with being in love.

33. Through Da Storm by Polo G

In "Through Da Storm," Polo G reflects on his struggles and the obstacles he has overcome to achieve success. The song captures the resilience and determination that has allowed him to persevere through tough times.

With lyrics that are both personal and relatable, Polo G reminds us of the importance of never giving up, even when things seem impossible.

34. Falling by Trevor Daniel

"Falling" is a melancholic love song that explores the pain and heartbreak that can come with a failing relationship. Through emotional lyrics and a haunting melody, Trevor Daniel captures the feeling of falling out of love and the heartache that comes with letting go. The song is a reminder that love can be both beautiful and painful, and that sometimes the hardest thing to do is to move on.

35. Walls Taking by Kevin Gates

"Walls Taking" by Kevin Gates is a reflective track that explores the consequences of his past decisions and the struggles he has faced. Through introspective lyrics and a soulful delivery, Gates shows the vulnerability and complexity of his journey.

The song reminds us that even when we make mistakes, there is always a chance for redemption and growth, and that sometimes the greatest lessons come from our personal struggles.

36. me & ur ghost by blackbear

"Me & ur ghost" by blackbear is a song about the lingering memories of a past lover that haunt the artist, even though they've moved on. The lyrics express feelings of loneliness and heartbreak as the artist struggles to let go of the past.

The melancholic melody and somber tone of the song perfectly capture the emotions of a person struggling to move on.

37. Emotionally Scarred by Lil Baby

"Emotionally Scarred" by Lil Baby is a powerful and introspective song about the emotional scars left by past relationships. The lyrics are raw and honest, with Lil Baby admitting to feeling hurt and betrayed by those closest to him.

The song's somber melody and Lil Baby's vulnerable delivery create a deeply emotional experience for the listener.

38. Dance With The Devil by Immortal Technique

"Dance With The Devil" by Immortal Technique takes a harrowing journey into the depths of despair and desperation. The sad rap song tells the tragic tale of a young man who falls victim to the lure of street life, only to be consumed by violence and betrayal.

Immortal Technique's gritty storytelling and vivid imagery paint a chilling portrait of the destructive consequences of greed and ambition. The haunting instrumental sets the tone for this cautionary tale, leaving listeners haunted by its powerful message long after the song ends.

39. MAYBE by The Kid LAROI

"MAYBE" by The Kid LAROI is a heart-wrenching track about the pain of unrequited love. The lyrics express the artist's desperation for the attention and affection of someone who doesn't feel the same way. The song's melody is haunting and emotive, perfectly capturing the feeling of heartbreak and longing.

40. Forever Never by PnB Rock (feat. Swae Lee & Pink Sweat$)

"Forever Never" by PnB Rock (feat. Swae Lee & Pink Sweat$) is a mournful song about lost love. The lyrics describe the aftermath of a painful breakup, with the artist lamenting the fact that the relationship is over. The song's melody is melancholic and dreamy, creating a sense of nostalgia and longing that makes it a powerful reflection on lost love.

41. scars by Baby Keem

"Scars" by Baby Keem is a haunting track where the rapper reflects on his inner demons and emotional scars. Keem’s delivery is emotional and raw as he lays out his thoughts and feelings over a simple and moody beat. The lyrics are introspective and speak to the personal struggles of navigating life while dealing with mental health issues and personal trauma.

42. Song Cry by Jay-Z

"Song Cry" by Jay-Z is a soulful reflection on the pain and heartache that accompanies lost love. Jay-Z uses an emotive delivery paint a vivid picture of vulnerability and regret as he grapples with the aftermath of a failed relationship.

The somber piano melody underscores the raw emotion in his voice, creating a haunting atmosphere that resonates with listeners who have experienced similar heartbreak.

43. I Don't Wanna Do This Anymore by XXXTENTACION

"I Don't Wanna Do This Anymore" by XXXTENTACION is a sad rap song where the late rapper opens up about his struggles with depression and suicidal thoughts.

X pours his heart out, conveying his feelings of hopelessness and despair, and the pain that comes with fighting inner demons.

44. Not Enough by Juice WRLD

"Not Enough" by Juice WRLD is a deeply personal and emotional song where the late rapper reflects on his inner struggles and insecurities. The song features a simple and melancholic beat, allowing Juice's lyrics and delivery to take center stage.

He speaks candidly about his struggles with addiction, depression, and anxiety, and the difficulties of finding happiness and fulfillment in life.

45. complicate it by iann dior

"Complicate It" by iann dior is a moody and introspective track where the rapper reflects on the complexities of love and relationships. The song features a mellow and atmospheric beat that sets the tone for iann's introspective lyrics. He touches on the ups and downs of love and how sometimes it can be difficult to navigate the complexities of relationships.

In Conclusion

In conclusion, the sub-genre of sad rap has gained immense popularity over the years due to its relatable themes of heartbreak, addiction, and depression.

Our playlist of the 250 best sad rap songs pays homage to the late rappers who have shaped and popularized the genre, such as Juice WRLD, XXXTENTACION, Lil Peep, and Mac Miller.

To listen to our playlist of sad rap songs, click here.

These songs serve as a reminder that even in the midst of darkness, there is beauty in vulnerability and self-expression.

We hope you enjoy our collection of sad rap songs! Until next time!