When a heartrending melody grips you like a vice, it’s truly magical. The late XXXTentacion was a master at channeling raw emotion and vulnerability into his work, often leaving listeners captivated and exposed.
With a unique ability to fuse genres and narrate the deepest complexities of human emotion, his music continues to leave an indelible mark on fans’ hearts.
As you delve into our carefully selected list of the saddest XXXTentacion songs, join us in celebrating an artist who continues to transcend musical boundaries through his poignant storytelling.
1. “I spoke to the devil in miami, he said everything would be fine” – (2022)
🎵 Song Name: I spoke to the devil in miami, he said everything would be fine
🧑 Artist: XXXTENTACION
💿 Album: LOOK AT ME: THE ALBUM
📅 Release Date: 2022
🕒 Song Duration: 2 minutes 59 seconds
The song “I spoke to the devil in miami, he said everything would be fine” by XXXTENTACION, from the album LOOK AT ME: THE ALBUM, captivates listeners with its haunting tale of a conversation between the artist and the devil. The somber lyrics provide insight into the dark depths of the singer’s mind, discussing feelings of hopelessness and heartbreak.
This song stands out as one of XXXTentacion’s saddest tracks, largely due to its chilling atmosphere and lyrics that allude to embracing darkness. The mysterious outro adds an unsettling twist to the song, underlining its eerie impact on listeners.
2. “ALONE, PART 3” (2018)
🎵 Song Name: ALONE, PART 3
🧑 Artist: XXXTENTACION
💿 Album: ?
📅 Release Date: 2018
🕒 Song Duration: 1 minutes 50 seconds
“ALONE, PART 3” by XXXTENTACION, from the 2018 album ?, is a raw emotional track that showcases the late artist’s vulnerability. Revolving around themes of love, self-worth, and heartbreak, it manages to strike a chord with listeners who can relate to feelings of loneliness and despair.
One of the song’s most poignant moments is when he sings about digging his nails into his arms after being rejected by a love interest. This sadness and vulnerability make “ALONE, PART 3” one of the most touching and mournful songs in XXXTENTACION’s discography, and a testament to his immense songwriting talent.
3. “Orlando” (2017)
🎵 Song Name: Orlando
🧑 Artist: XXXTENTACION
💿 Album: 17
📅 Release Date: 2017
🕒 Song Duration: 2 minutes 44 seconds
“Orlando” from XXXTENTACION’s 2017 album 17 delves deep into themes of emotional pain, mental health struggles, and self-reflection. Sad and introspective, this song captures the artist’s inner turmoil as he vividly describes his experiences with loneliness, depression, and the desire for an escape.
The lyrics are raw and honest, making it one of the saddest XXXTENTACION songs. Listeners who can relate to these emotions may find solace in the authenticity of the track.
Ultimately, despite its dark themes, “Orlando” stands out as a powerful representation of vulnerability in a world where many artists shy away from exposing their inner pain.
4. “NUMB” (2018)
🎵 Song Name: NUMB
🧑 Artist: XXXTENTACION
💿 Album: ?
📅 Release Date: 2018
🕒 Song Duration: 3 minutes 6 seconds
“NUMB” from the album ? is a heartrending track by XXXTENTACION released in 2018. This melancholic song depicts emotional pain and the struggle of coping with it every passing year.
The repetitive lyrics emphasize that the singer feels trapped in a seemingly never-ending cycle of drowning in their tears. The song has resonated with many listeners due to its raw honesty and vulnerability, making it one of the saddest XXXTentacion songs.
The haunting melody and poignant lyrics, where the singer asks for relief, display the turmoil experienced by the artist, which leaves a lasting impact on the audience.
5. “Ecstasy” Feat. Noah Cyrus (2019)
🎵 Song Name: Ecstasy
🧑 Artist: XXXTENTACION
🧑 Featured Artist(s): Noah Cyrus
💿 Album: Bad Vibes Forever
📅 Release Date: 2019
🕒 Song Duration: 4 minutes 0 seconds
“Ecstasy” by XXXTENTACION featuring Noah Cyrus is a standout track from the posthumous album Bad Vibes Forever. This heart-wrenching song explores themes of love, loss, and self-discovery.
The lyrics, “I thought you got all you came for, lover… All or nothing aren’t the same score,” showcase the emotional turmoil experienced in relationships.
XXXTENTACION’s verse discusses his struggles with mental health and self-identity, while Noah Cyrus provides a haunting and mesmerizing accompaniment. With its raw and visceral emotions, “Ecstasy” is undeniably one of the saddest songs from XXXTentacion, leaving a lasting impact on listeners.
6. “I Don’t Wanna Do This Anymore” (2017)
🎵 Song Name: I Don’t Wanna Do This Anymore
🧑 Artist: XXXTENTACION
💿 Album: Revenge
📅 Release Date: 2017
🕒 Song Duration: 1 minutes 28 seconds
The song “I Don’t Wanna Do This Anymore” from the album Revenge by XXXTENTACION captures the raw and unfiltered emotions of heartache and longing. The lyrics express the artist’s struggle with feelings of worthlessness and yearning for love while grappling with understanding his self-worth.
The chorus emphasizes this internal battle as he sings “you’re my only one,” highlighting the emotional dependence he feels on his lover. This introspective track leaves a profound impact on listeners, who may relate to these vulnerable emotions, making it one of the saddest XXXTentacion songs in his catalogue.
7. “WingRiddenAngel” (2022)
🎵 Song Name: WingRiddenAngel
🧑 Artist: XXXTENTACION
💿 Album: LOOK AT ME: THE ALBUM
📅 Release Date: 2022
🕒 Song Duration: 2 minutes 47 seconds
“Riddled with emotion and haunting imagery, “WingRiddenAngel” from XXXTENTACION’s album LOOK AT ME: THE ALBUM takes the listener on a sorrowful journey. The lyrics explore themes of loss, depression, and heartache, making it one of XXXTentacion’s saddest songs.
The poignant line, “I shot an angel with my father’s rifle,” embodies the internal struggle of guilt and forgiveness, while the refrain, “Grow your wings, fly away,” signifies the desire to release loved ones trapped in pain. Touching the hearts of fans worldwide, this track unapologetically reveals the depths of human despair and vulnerability.
8. “Save Me” (2017)
🎵 Song Name: Save Me
🧑 Artist: XXXTENTACION
💿 Album: 17
📅 Release Date: 2017
🕒 Song Duration: 2 minutes 43 seconds
“Save Me” by XXXTENTACION from the 2017 album 17 is a raw, emotional expression of the late rapper’s battle with depression and loneliness. The introspective lyrics depict his personal struggle, asking for someone to save him from the darkness he’s experiencing.
A powerful aspect of the song is its honest vulnerability, with lines like “Heaven and hell, my friend / I won’t shed a tear / Let them see me in pain again.” The somber tone and haunting melody create an atmosphere that resonates with listeners struggling with similar emotions, making it one of the saddest songs in XXXTentacion’s repertoire.
9. “KILL ME (Pain From The Jail Phone)” – (2022)
🎵 Song Name: KILL ME (Pain From The Jail Phone)
🧑 Artist: XXXTENTACION
💿 Album: LOOK AT ME: THE ALBUM
📅 Release Date: 2022
🕒 Song Duration: 2 minutes 19 seconds
“KILL ME (Pain From The Jail Phone)” by XXXTENTACION, from the album LOOK AT ME: THE ALBUM (2022) dives into the raw emotions of a broken heart, making it one of his saddest songs. The lyrics, “How’s it feel with your broken heart?” and “Heart broken, no one can feel me,” emphasize the sense of isolation and despair.
The repetition of “Kill me now, numb the pain,” highlights the desperation to escape the emotional turmoil. Impacting listeners by its honest portrayal of heartache, the song powerfully showcases XXXTENTACION’s vulnerability and emotions.
Pain and heartbreak take center stage in this heartfelt track.
10. “let’s pretend we’re numb” – (2015)
🎵 Song Name: let’s pretend we’re numb
🧑 Artist: XXXTENTACION
💿 Album: let’s pretend we’re numb
📅 Release Date: 2015
🕒 Song Duration: 1 minutes 20 seconds
In “Let’s Pretend We’re Numb” from the album Let’s Pretend We’re Numb, XXXTENTACION touches on some of his deepest emotions. The song starts with a powerful intro urging listeners not to hide their feelings, and throughout the verse, he vividly conveys feelings of jealousy, love, and loss.
This heartfelt approach makes it one of the saddest songs in his discography. One key line, “Think I ripped the wings off of my fuckin’ angel,” signifies regret and despair.
His vulnerability in “Let’s Pretend We’re Numb” has a profound impact on listeners, reminding them of the importance of communication and emotional honesty.
11. “changes” (2018)
🎵 Song Name: changes
🧑 Artist: XXXTENTACION
💿 Album: ?
📅 Release Date: 2018
🕒 Song Duration: 2 minutes 2 seconds
“Changes” by XXXTENTACION, from the 2018 album ?, is a heart-wrenching ode to a crumbling relationship. Featuring vulnerable lyrics and a tender melody, this melancholic track strikes a powerful chord with listeners.
The song’s raw emotion is evident in lines like “My heart can’t take this damage, And the way I feel, can’t stand it.” Showcasing the transformative power of love, “Changes” highlights the pain that arises when everything seems to fall apart. The collaboration between XXXTENTACION and PnB Rock adds depth to the song’s overall impact, making it one of the saddest XXXTentacion songs to date.
12. “Carry On” (2017)
🎵 Song Name: Carry On
🧑 Artist: XXXTENTACION
💿 Album: 17
📅 Release Date: 2017
🕒 Song Duration: 2 minutes 10 seconds
“Carry On” by XXXTENTACION is one of the heart-wrenching tracks from his 2017 album 17. The song allows us to witness the vulnerability of the late artist as he navigates through feelings of betrayal, heartbreak, and loss.
With deeply personal lyrics, listeners can’t help but feel a connection, as he bravely confronts his pain with raw emotion. Notable for its simplicity, the track features the haunting vocals of Shiloh Dynasty on the intro and outro. This sets the perfect tone for XXXTENTACION’s confession of lingering love despite resentment and inner turmoil.
The impactful chorus urges listeners to “carry on” through life’s struggles, just as he does while grappling with “this pain inside of my chest.” Drawing from his own struggles and experiences, XXXTENTACION manages to evoke a sense of camaraderie and hope, making “Carry On” one of the standout, melancholic songs of his prolific career.
Music has always been a big part of my life. Now I want to share my passion for music with the world. Some of my favorite genres of music include pop, rap, dance, and electronic. Let’s make the world a better place with music!
