The 20 Saddest Rap Songs of all time

Over the years, hip-hop has birthed numerous tracks delving into emotional darkness and depression. Originating from the struggles of urban life, it’s no surprise that some lyrics mirror these hardships and their impact on mental well-being. Just like anyone else, today’s rappers and hip-hop artists navigate their own personal challenges. What better outlet to channel these emotions than through the mic, allowing them to vent and express themselves freely? Here’s our compilation of 20 of the saddest rap songs of all time.

1. Life Goes On – 2Pac

In the words of 2Pac, ‘It’d be a lie if I told you that I never thought of death, my nigga, we the last ones left.’ ‘Life Goes On’ earns its spot as one of the saddest rap songs ever. 2Pac transcended being just a rapper; he was a voice for grappling with real-life challenges and adversity. So, chin up, my friend, because 2Pac crafted this song just for you.

2. Lucid dreams – Juice Wrld

It’s quite impossible to ignore Juice Wrld‘s laments in one of his most successful songs ever ‘Lucid dreams’. The Chicago rapper processed a nasty breakup by plunging into the depths of his grief and regret. Since its release, it has garnered over 2 billion streams on Spotify, showcasing the song’s immense impact on listeners. Throughout history, “Lucid Dreams” will forever be recognized as one of the 20 saddest rap songs ever created.

3. What are you so afraid of – XXX Tentacion

XXXTentacion’s ‘What are you so afraid of’ is the track that hits you right in the feels from the get-go. X had a way of reaching deep into his psyche and translating it into music that resonated with millions. This sad song, slow and melodic, likely describes a specific chapter of the rapper’s life. Let’s face it, X had a repertoire of over 5 sad songs that could easily make the cut, but for now, let’s spotlight this song. Long Live  X.

4. The Abyss – Dax

Dax’s ‘The Abyss’ offers a vivid and detailed account of his origin story, albeit one tinted with darkness and sadness. “All of this pain, I just wanna be happy,” Dax passionately delivers over a minimalist beat, reflecting on his childhood struggles with psychosis. However, amidst the darkness, the track takes on a glimmer of hope as Dax explores ways to channel his pain into art.

5. Beautiful – Eminem

Eminem‘s track “Beautiful” from the album Relapse showcases his storytelling skills. With raw honesty, he croons, “I’m just so fucking depressed, I just can’t seem to get out this slump.” This song is considered by both fans and critics as the strongest song on Relapse. At its core, this is a song about sadness and depression, but by the end of the track, Eminem expresses optimism and hope for the future. 

6. Suicidal – ynw melly

In “Suicidal,” YNW Melly explains the profound anguish and bitterness stemming from a tumultuous breakup with his significant other. He vividly articulates the pain by likening it to the act of consuming drugs and Hennessy, a French cognac, as a means to numb the memories of their relationship. This too, is undoubtedly one of the 20 saddest rap songs ever made!

7. Red Moon – Lil Uzi Vert

“Red Moon” finds Lil Uzi Vert contemplating a shifting relationship, stirring emotions akin to those in “Patience” from his third studio album, Pink Tape. This introspective track aligns with Uzi’s mindset during the recording of his fourth album, Luv Is Rage 3, a project rumored to mark his retirement from music.

8. Broken Smile (My All) – Lil Peep

“Broken Smile (My All)” serves as the opening track on Lil Peep’s posthumous album, Come Over When You’re Sober, Pt. 2. The song’s introduction features a snippet from Lil Peep’s verse on Craig Xen’s track, “UNBREAKABLE,” released in November 2015. Thematically, “Broken Smile (My All)” sets the tone for the album, exploring themes of loss, sadness, and longing. The title suggests the subject of the song, presumably Lil Peep’s lover, bears a smile marred by brokenness, evoking imagery of a face consumed by painful hopelessness, mirroring the emotions of the other person involved.

9. If you want love – Nf

In “If You Want Love,” NF talks about the core components of love, emphasizing the necessity of enduring life’s challenges and being open to growth and change in order to experience genuine love both for oneself and from others.

NF has previously explored themes surrounding love, echoing sentiments reminiscent of his earlier track, “Thing Called Love.” The laid-back atmosphere of the song, characterized by slow-paced balladry, gentle guitar chords, and harmonizing background vocals, creates a tranquil ambiance.

10. Marvins Room – Drake

The song portrays Drake in a state of tipsiness as he reaches out to a former lover, expressing his deep sense of solitude. He reflects on the shared memories they once cherished together while attempting to persuade her to reconsider her current relationship and return to him.

11. Left For Dead – Trippie Redd

In “Left 4 Dead,” the third commercial single from A Love Letter To You 5, Trippie Redd confronts the betrayal of his former lover who abandoned him in a critical moment.

The song bears a subtle resemblance to “Leray,” a track dedicated to fellow artist Coi Leray, whom Trippie dated from 2018 until late 2019. “Leray” delves into Trippie’s realization of his own emotional journey following their breakup, expressing: “I wasn’t necessarily seeking happiness, just aiming to alleviate the pain.”

12. Moment – Ivan B

Ivan B’s track “Moment” features slow, intense beats, with verses that unveil numerous truths, resonating with a weary mind that feels introspective and detached. The phrase “I just need a moment of my own” encapsulates the essence of the song, without requiring any additional explanation from an outside source.

13. Hello There – Lyrical lemonade, Lil Tracy, Corbin & Black Kray

“Hello There” is the third single off Lyrical Lemonade’s compilation album, All Is Yellow, serving as an homage to Blink 182’s “I Miss You.” This iconic track from Blink-182 vividly portrays the toll depression can take on a relationship, leading to its eventual dissolution.

“I Miss You” delves into the haunting essence of yearning and grief, exploring themes of nostalgia, emotional upheaval, and the enduring presence of a past love that lingers like a ghostly specter in the mind. It poignantly captures the struggle of coping with the absence of a significant other and the pervasive sadness that accompanies memories of a once-intimate connection.

14. Depression – Quado Rondo

In his track “Depression,” Quando Rondo croons, “Bank account on overload, but I’m still broke in spirit. ‘Depression’ what he suffers from, same words from Doctor Henry. It ain’t no love inside the slums, know if they could, they’d kill me.” These lyrics paint a vivid picture of an artist grappling with inner turmoil and profound pain. It`s only right that it is ranked amongst the 20 saddest rap songs of all time. 

15. 1-800-273-8255 – Logic, Alessia Cara, Khalid

In “1-800-273-8255,” Logic emphasizes that suicide is not a solution to life’s challenges. He aims to raise awareness about the support available to those struggling, including the National Suicide Prevention Lifeline, whose phone number serves as the title of the song. Despite the introduction of the new phone number 9-8-8 for the lifeline since 2022, the original number remains operational. In fact, the song was released in collaboration with the NSPL as part of efforts to promote mental health awareness and suicide prevention.

16. Count me out – Kendrick Lamar

“Count Me Out” kicks off the second disc and marks the 10th track overall on Mr. Morale & The Big Steppers. The song revolves around Kendrick confronting a significant individual from his past whom he strives to prove wrong, despite still harboring love for them.

Throughout the track, Kendrick undergoes a personal transformation, feeling compelled to become more open in his relationship. By the song’s conclusion, he comes to the realization that he deserves better than this person, and expressing his truth and exiting the relationship ultimately leads to a sense of contentment and happiness. This stands in contrast to the negative and miserable emotions he previously experienced while attempting to mend a situation he found himself entangled in.

17. Welcome to heartbreak – Kanye West, Kid Cudi

In “Welcome to Heartbreak,” Kanye West shares his introspections on how, despite his wealth and fame accrued from his career, he feels ensnared and distant from what he deems as the ideal way to live – the “good life.” He experiences estrangement from loved ones who are embarking on milestones like starting families and getting married, as his demanding work schedule leaves him with little time for personal connections. Consequently, he compensates for this absence by resorting to material possessions.

18. Rodwave – Boyz don’t cry

“Boyz Don’t Cry” is a single from Rod Wave’s album ‘Nostalgia.’ The soulful Florida rapper lays bare his emotions in this track, which can be described as a fusion of country melodies with twinkling guitars and trap-infused drums. Structurally, the song consists of one continuous verse followed by a single chorus. As the track unfolds, listeners are introduced to a visibly distraught Rod Wave, who finds himself on the road grappling with the aftermath of a recent breakup.

19. Mirror – Lil wayne, Bruno Mars

Featuring a sung portion by Bruno Mars, who himself has sparked various opinions, this song delves into Weezy’s past entanglement with drugs and contemplates the trajectory it might set for his future.

Significantly, the entirety of the track portrays Wayne engaging in a conversation with his reflection in a mirror, engaging in introspection to gain a deeper understanding of himself as “Wayne.”

20. Through Da Storm – Polo G

“In ‘Through da Storm,’ the third track of Polo G’s debut album ‘Die A Legend,’ Polo G delves into themes of religious faith and familial dedication. He candidly shares his experiences of pain and adversity, offering words of encouragement to persevere. Additionally, Polo G doesn’t shy away from flaunting his wealth throughout the track.”

To spare you the hassle of searching for them one by one, here’s a playlist featuring all 20 of the saddest rap songs. Take a moment to meditate and recharge while listening.

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