We have put together this list of the saddest rap songs for your reading and listening pleasure. All the track on this list of sad rap songs has a touchy story subject to it.
Saddest Rap Songs and our take on them

Most rap songs are about the bling, the good life, women, and fame but some rap songs touch on subjects that put them in the category of the saddest songs ever.
In this article, we have chosen to write and explore those sad rap songs that delve into a theme of hurt, loss, failure, depression, hate, and death. So, the following rap songs are the saddest rap songs that feature one or more of the subjects above.
Like anyone else, these rap artists go through their own daily struggles too just like anybody else. When they do, they get on the mic to vent about it by performing a sad rap song. Here are the saddest rap songs according to our play count and request for these types of songs over the last nineteen years.
All That I Got Is You – Ghostface Killah featuring Mary J. Blige
“All That I Got Is You" is a poignant hip-hop song by Ghostface Killah featuring Mary J. Blige. Ghostface Killah is a member of the W-Tang Clan however this song is from his debut solo album, "Ironman," released in 1996. The song reflects on Ghostface's upbringing in a poverty-stricken neighborhood and the challenges he faced growing up.
Ghostface Killah narrates his personal story of struggle while growing up with his mother and sisters when his daddy left them at 6 years of age. Mary J. Blige's soulful vocals complement the introspective nature of the song, adding depth and emotion to the narrative. This song made our list of saddest rap songs because of Ghostface Killah’s sad narrative of struggle.
Ballad of Worms – Cage
"Ballad of Worms" is a dark and introspective hip-hop track by Cage, released in 2005 as part of his album "Hell's Winter." The song delves into the artist's personal struggles in rap music industry. He used an ill and dying girlfriend as a metaphor for his struggles with addiction, mental health, and the pressures of the music industry. With gritty and haunting lyrics, Cage paints a vivid picture of his inner demons and the self-destructive patterns he grapples with. "Ballad of Worms" showcases Cage's raw and emotive storytelling, providing a glimpse into the depths of his troubled psyche and the battle for redemption.
Hold Ya Head - The Notorious B.I.G featuring Bob Marley
We have gone for “Hold Ya Head” instead of “Suicidal Thoughts” simply because this features the iconic Bob Marley vocals. It is a story told by Notorious B.I.G. about where he wants to go when he dies.
The track delves into the darkest corner mind of a person who is fed up and contemplating suicide. He explores many ways to kill himself and is aware that there is no coming back from that. It shows a person that is wrestling with inner demons and needs help.
This song is a remake of his 1994 song “Suicidal Thoughts” as part of his album "Ready to Die." Notorious B.I.G leaves a lasting impact on listeners with its stark honesty and emotional depth.
Crossing Over – Prozak
"Crossing Over" is from Prozak’s album called "Tales from the Sick." The song starts with the Lord’s prayer and the sound of labored breathing. It’s a story of an individual who is laying in a hospital bed in a state of comatose. He was just being kept alive by a respirator.
Prozak paints a vivid picture of the spiritual being circulating at the bedside of the individual waiting for him to take his last breath. The Strangeland Music artist nailed this song with his rap style and lyrics.
Beautiful – Eminem
"Beautiful" is an introspective and vulnerable sad rap song by Eminem, released in 2009 as part of his album "Relapse." The track reflects on Eminem's personal struggles with fame, addiction, and self-doubt. He delves into his darkest moments and expresses the desire to find peace and regain control of his life making it one of the saddest rap songs.
Eminem told Vibe Magazine that he wrote a verse and a half of this sad rap song while he was in rehab. Throughout the song, Eminem confronted his inner demons with heartfelt lyrics and introspective verses. He offered a glimpse into his emotional journey towards self-acceptance addressing his own vulnerabilities.
Brenda's Got A Baby – 2Pac
"Brenda's Got a Baby" is a powerful and socially conscious hip-hop song by 2Pac, released in 1991. The track tells the tragic story of a 12-year-old girl named Brenda. She became pregnant but didn’t get the support of her family or the baby daddy.
In the harsh reality of poverty, neglect, and despair, Brenda had the baby in the toilet, didn’t have money to fend for the child, got herself into more woes, and ended up getting killed. In this song, 2Pac addressed the themes of teenage pregnancy, poverty, and social injustice in marginalized communities. Although this song is 31 years old, some of the issues in this sad rap song are still challenges faced by young women in disadvantaged environments.
Acid Rain – Chance the Rapper
"Acid Rain" is an introspective sad rap song by Chance the Rapper, released in 2013 as part of his mixtape "Acid Rap." The track explores Chance's personal journey and the challenges he faces as an artist and individual.
This is Chance the Rapper’s most introspective song to date. He reflects on the impact of fame, the struggles of self-discovery, and the harsh realities of the world.
Through his lyrics, Chance delivers a candid and thought-provoking examination of his own psyche and the search for meaning in a chaotic world. His delivery of this song and the deep meaning of the lyrics make it one of our saddest rap songs
Anxiety Attacks – Wrekonize
"Anxiety Attack" is a gripping relatable sad rap song by Wrekonize, released in 2011. The song delves into the personal struggles of dealing with anxiety and its debilitating effects. Wrekonize opens up about his overwhelming emotions, racing thoughts, and the constant battle with his inner demons. In the video, he can be seen visiting a psychiatrist to pour out his thoughts and get help.
Colored Dreams – Reason
"Colored Dreams" is a sad rap song by Reason, released in 2018 as part of his album "There You Have It." The song delves into the realities of a convicted murderer’s life imprisonment.
He struggles with the reality of his actions and the pain he had caused the family of the deceased. The circumstances of his violent act were that of gang violence.
This action broke his mother, and he knew it. As he sat in his jail cell, he wrote a letter to her before hanging himself. This is one of the saddest rap songs as Reason's evocative lyrics paint a vivid picture of the harsh realities faced by individuals trapped in cycles of poverty and violence.
D Rugs – Cam'ron featuring Brotha
"D Rugs" is a gritty and vivid hip-hop track by Cam'ron, released in 2002 as part of his album "Come Home with Me." The song provides a raw portrayal of the drug game and its impact on the community. Cam'ron rapped about a boy whose mum was a drug user while she was pregnant with him.
At the time of the pregnancy, she was dating a foreign drug pusher. 10 years later the boy was introduced to the drug game by the same man. It didn’t end well for the boy or the mother.
Cam'ron narrates the story of street life, survival, and the consequences of getting caught up in the world of drugs. "D Rugs" is a sad rap song that serves as a stark reflection of the unforgiving streets and the choices individuals face within that environment.
Dance With The Devil – Immortal Technique
"Dance with the Devil" is a haunting and sad rap song by Immortal Technique, released in 2001 as part of his album "Revolutionary Vol. 1." The track delves into a dark and disturbing narrative of crime, betrayal, death, and the consequences of one's choices.
Immortal Technique's raw and intense lyrics on this four-verse sad rap song paint a vivid picture of a young man's descent into a world of violence and moral decay. "Dance with the Devil" tells a story of a young man who wanted street creds but ended up doing something he could never be able to live with. Listen to this sad rap song to find out more.
Dead Homiez – Ice Cube
Church bells tolling, the Hurst, and black and white music video. "Dead Homiez" is a somber ode rap song by Ice Cube, released in 1991 as part of his album "Death Certificate." In the song, Ice Cube reflects on the harsh realities of life in the inner city. This song is about a friend whom Ice Cube lost to gang violence.
He used this track to vent his loss and mourn the death of his friend. The rap artist’s fervent lyrics delve into themes of grief, and the cyclical nature of gang violence.
The rap video collaborates with the lyrics. The black and white music video features church bells tolling, black limos, and a hearse carrying his dead homie and the family of his dead homie. The visuals of this rap song show sadness and it makes our cut for the saddest rap songs.
I Never Seen a Man Cry – Scarface
"I Never Seen a Man Cry" is an emotionally charged sad rap song by Scarface, as part of his album "The Diary" (1994). The track explores the struggles and choices of a man who had just finished serving time in prison.
Scarface's introspective lyrics delve into the internal battles faced by an individual who had lost his way after prision. He found himself killing another man due to societal pressures and oppression.
The rap video features sad dark scenes, and this is a common theme with sad rap videos from this era. They are shot in black and white to emphasize the grief. "I Never Seen a Man Cry" reached number 2 on the Hot Rap Songs chart but was prevented from the top step by 69 Boyz’s “Tootsee Roll.”
Death Enclaimed – YoungBoy Never Broke Again
"Death Enclaimed" by NBA YoungBoy is a sad hip-hop song that narrates the artist’s paranoia of betrayal from those close to him. Also known as YoungBoy Never Broke Again, NBA YoungBoy’s raw and vulnerable storytelling, allows listeners to connect with his journey and the hardships he has endured in his personal life.
Good Die Young – D12
"Good Die Young" is a sad rap song that paid homage to a friend of D12’s. Released in 2004 as part of their album "D12 World," the rap song was dedicated to their friend Bugz. He died over something the group claimed was insignificant.
The track also pays tribute to other friends and loved ones who had tragically passed away. D12 reflects on the harsh realities of life, the pain of losing loved ones, and the fragility of mortality.
A 5-verse song with heartfelt lyrics and somber tones, "Good Die Young" serves as a touching and emotional tribute, reminding listeners of the preciousness of life and the need to appreciate and cherish every moment.
Happy Birthday – Flipsyde
This is definitely one of the saddest rap songs of all time. It is very touchy, but you won’t know that from the title. "Happy Birthday" by Flipsyde, was released in 2005 as part of their album "We the People."
After regretting an abortion, he takes the listener through a lot of complicated dilemmas and heartbreaking questions that would bring a tear to your eyes.
In Flipsyde’s mind, abortion is on the same level as murder, and he wonders how he could have ever committed murder consciously. He reflects on what the child would have been if only he had kept the pregnancy and not paid for the abortion. When listening to this song, you could understand why abortion is illegal in some States in the US.
I Fall Apart – Post Malone
This soulful and emotional ballad is a song about love and heartbreak. Post Malone recalls a heartbreak he experienced in high school. The song delves into the pain, hurt, and heartbreak felt by a failed relationship.
"I Fall Apart" was a single from his 2016 album “Stoney.” It debuted on the Billboard Hot Rap Songs chart at number 20 and peaked at 8. Post Malone's heartfelt vocals and introspective lyrics capture the vulnerability and despair of a broken heart. He reflects on the crumbling of love, dealing with the aftermath of a breakup, and the struggle to move on.
I Feel Like Dying – Lil Wayne
"I Feel Like Dying" is a haunting and introspective song by Lil Wayne, released in 2007 as part of his mixtape "The Drought Is Over 2." In some of his songs, Lil Wayne usually eulogizes the use of drugs, however, this is the reverse.
The track delves into themes of drug addiction, and the desire to escape from reality. Lil Wayne's lyrics paint a vivid picture of the dark thoughts and emotions that consume him when on drugs.
This tune contains a sample from the song “Once” by the folk singer Karma-Ann Swanepoel (2003). Wayne and his label were sued by the folk singer and her publishing company for financial relief due to infringement of the sample.
I'll Be Missing You – Puff Daddy featuring Faith Evans & 112
"I'll Be Missing You" mourns the loss of a loved one and expresses the pain and longing that follows. Puff Daddy's emotional lyrics combined with Faith Evans' powerful vocals and 112's harmonies create a memorable homage to their friend and lover (In Faith’s case).
"I'll Be Missing You" captures the essence of grief felt by The Notorious B.I.G.'s crew making this one of the saddest rap songs. It left a big hole in the hearts of the members of Bad Boy Entertainment, but the enduring legacy and impact of Big Poppa on the music industry is still felt today.
This song debuted on the Billboard Hot 100 at number 1 three months after the death of The Notorious B.I.G. It spent 11 weeks at the top of the chart making it a hit record for Puff Daddy at the time. It sampled the hit song “Every Breath You Take” by the Police (1983).
Jocelyn Flores – XXXTENTACION
"Jocelyn Flores" is a sad rap song by XXXTENTACION, released in 2017 as part of his album "17." The track pays tribute to Jocelyn Flores, a friend of XXXTENTACION who tragically took her own life.
While staying with X in Florida for a photo shoot, Jocelyn Flores, a friend of X's, suffered depression and committed suicide. This act troubled X and he felt like there was nothing else to live for as he felt responsible for her death.
The lyrics delve into themes of mental health, depression, and the struggles faced by individuals battling inner demons and suicidal thoughts. XXXTENTACION's emotive vocals and introspective storytelling offer a glimpse into the pain and turmoil experienced by both Jocelyn Flores and the X himself.
Kim – Eminem
"Kim" is a raw and intense sad rap song by Eminem, released in 2000 as part of his album "The Marshall Mathers LP." The track takes the form of a disturbing and graphic narrative, exploring the troubled relationship between Eminem and his ex-wife Kim.
Eminem's lyrics depict a violent and chaotic scenario, reflecting his anger and frustration. "Kim" showcases Eminem's ability to create vivid storytelling through his words, but it also serves as a reflection of the turbulent emotions and personal demons that he has battled throughout his life.
When listening to the song, you could hear the hate and anger in his voice. If I was Kim and hear this song by my supposed husband, I would run away and never look back. How can you wish death on your wife? This is one of the saddest rap songs ever.
Last Good Sleep by Company Flow
"Last Good Sleep" is a haunting and introspective hip-hop song by Company Flow, released in 1997 as part of their album "Funcrusher Plus." The track delves into themes of an abusive relationship from the viewpoint of a young boy.
It narrates a story of a young boy who sees his stepdad abuse his mother regularly. The lyrics explore the dark corners of the mind of a young boy, who is haunted by the verbal abuse suffered by his mother at night. This sends him into emotional turmoil and existential contemplation.
This experience traumatized the young boy and even in his adult age, he still hears his stepdad physically abusing his mum. It is sad to imagine what this boy might have gone through. From the viewpoint of a child, this song makes our list of the saddest rap songs.
We'll Always Love Big Poppa – The LOX
There is no doubt that this is one of the most heartfelt tributes to The Notorious BIG, along with "I'll Be Missing You" by Puff Daddy and family. Released in 1997 by the LOX, "We'll Always Love Big Poppa" is a heartfelt and homage-filled sad rap song that paid tribute to the late Notorious B.I.G.
The rapper was caught in the middle of the East and West Coast wars and this song recounts BIG’s legacy and its impact on the music industry.
The LOX's lyrics combine admiration, respect, and fond memories, expressing their love and eternal appreciation for Big Poppa. "We'll Always Love Big Poppa" serves as a testament to the enduring legacy of one of hip-hop's greatest artists.
Long Gone (Save Me From This Hell) by $Uicideboy$
This sad rap song delves into themes of inner mental health struggles, drug addiction, and the desire to escape from it all by ending it. $Uicideboy$, released this track in 2017 as part of their album "Eternal Grey."
$Uicideboy$'s haunting lyrics paint a vivid picture of pain, despair, and a yearning for freedom from personal demons.
With the dark and atmospheric production of this sad rap song, the group showed a blend of introspective lyricism and haunting soundscapes. They rapped about being in a room with the ghost of lost friends and referred to wanting to be laid to rest.
Marvins Room – Drake
"Marvins Room" is a melancholic song by Drake, released in 2011 as part of his album "Take Care." The track explores themes of loneliness, heartbreak, and hate. Drake's lyrics depict an intoxicated man who calls up his ex and expresses his feelings of longing and hate.
Drake's emotive vocals on "Marvins Room" captures the essence of the emotional vulnerability of a man who is reminiscing about an ex he clearly still loves. The song resonates with listeners who have experienced heartbreak and didn’t know how to deal with it.
Millie Pulled A Pistol on Santa – De La Soul
"Millie Pulled A Pistol on Santa" is a sad traumatic experience of a young girl. The track tells a powerful story of a girl named Millie, who grows up in an abusive household. She was getting sexually molested by her own father.
The story is told by a bunch of Millie’s friends whom she went to school with. Because of their own personal experience with Millie’s father, they used to think he was a cool dad and that she was lucky to have him. Unknowingly to them, he was the monster in white clothes.
This sensitive subject matter song was released in 1991 as part of their album "De La Soul Is Dead." It made our list of saddest rap songs because we can’t imagine what a little girl like Millie went through with such a father.
My Life – The Game Featuring Lil Wayne
"My Life" is a reflective song by The Game, featuring Lil Wayne, released in 2008 as part of his album "LAX." The track delves into gang crime that has claimed the lives of so many people in the communities.
The Game seems to have lost so many of his friends to gun violence and wondered why he was still alive. He struggles to understand the meaning of life and why the life of a human being could be cut short due to a meaningless feud. My Life is one of the numerous hit songs produced by Cool & Dre.
One Life – The Last Emperor featuring Poetic
"One Life" serves as a reminder to cherish each moment of life as well as know the fragility of it. With the rain and thunder sound effects, this collaboration between The Last Emperor and Poetic is chilling and dark.
The second verse by Poetic (A member of The Gravediggaz) narrates his personal story. He was diagnosed with cancer and only had a few months to live. Sadly, he succumbed to his illness and died on July 15th, 2001. "One Life" will forever stand as a testament to his courage and bravery and remain one of the saddest rap songs ever.
If I Ever Go – Krizz Kaliko
Krizz Kaliko is a Missouri rapper who helped put Kansas City on the map alongside Tech N9ne and Travis O'Guin who owns the independent label Strangeland Music.
In this song, Krizz Kaliko acknowledges that life doesn’t last forever and he knows one day he would be dead and gone. He urges those who love him to throw a party and celebrate him instead of mourning me.
The lyrics contemplate what would happen after he had taken his last breath, questioning the impact he has made on the lives of others and contemplating the nature of the afterlife, be it heaven or hell. “If I Ever Go” is a song by Krizz Kaliko from his 2019 album called Vitiligo.
Remember – Mac Miller
"Remember" is a poignant tribute song by Mac Miller to a friend called Reuben Eli Mitrani. Mac had dedicated this song to Reuben who sadly died in 2012. In addition to dedicating this song to Reuben, Mac also named his record label after his dear friend.
Years after his friend’s death, Mac still finds it difficult to accept the tragedy. In his lyrics, he seems to be self-denial because he said he would pay anything to find him. This is always the case when we lose someone so dear and close to us.
Renee – Lost Boyz
"Renee" is a song by Lost Boyz, released in 1996 as part of their album "Legal Drug Money" and on the soundtrack “Don't Be a Menace to South Central While Drinking Your Juice in the Hood.”
The track tells a sweet love story that has a tragic ending. It’s a song about a girl called Renee who met her untimely death by getting caught in the middle of a store robbery. In the 90s, store robbery was a common event in the “hood” and had led to many innocent lives lost.
At the time, she was unfortunate to be at the grocery store smelling some flowers when she met her death. Mr Cheeks (A member of the Lost Boyz) tells the story of how they met and connected on the same level. The future was bright for this young lady as she was studying to become a lawyer.
With a reflective tone and captivating storytelling, "Renee" serves as a compelling narrative that sheds light on the complexities and hardships faced by individuals in inner-city communities.
Retrospect for Life – Common Ft. Lauryn Hill
"Retrospect for Life" tells a story about two young people in a relationship. The girl found out she was pregnant and told her boyfriend about it. However, the boyfriend was not ready to take responsibility for the baby and asked her to abort it. The track explores the sensitive topic of abortion and the complex emotions and moral dilemmas that surround it.
Common and Lauryn Hill's lyrics delve into the perspectives of both the man and the woman involved, touching on themes of regret, responsibility, and the consequences of their choices. "Retrospect for Life" prompts listeners to reflect on the weighty issues surrounding reproductive rights and personal accountability.
Roses – Benny Blanco and Juice WRLD
This is another sad rap song that features Juice WRLD. The theme of the song is also about a sad heartbreak that makes the person involved feel betrayed. The breakup leaves him feeling insecure and disconnected from women because he had invested a lot into the relationship only to be broken-hearted.
Released in 2020, Benny Blanco's production creates a dreamy atmosphere with heartfelt and vulnerable verses by both artists. This is a relatable and emotive listening experience for those who have experienced the complexities of love and betrayal.
Runaway Love – Ludacris
"Runaway Love" is a socially conscious sad rap song by Ludacris, featuring Mary J. Blige, released in 2006 as part of his album "Release Therapy."
This song comes with three powerful verses from Ludacris. The verses shed light on the harsh realities faced by young girls who are victims of neglect, domestic abuse, and early pregnancy. The first verse covers the story of a 9-year-old girl whose mother’s boyfriend used to sexually harass her. Lisa told her mother about it, but her mother would not believe her.
The second and third verses are also chilling stories hence we have added this song to our list of saddest rap songs. You should listen to the song to find out the story in the second and third verses. With its impactful message and heartfelt delivery, "Runaway Love" serves as a call to address the societal issues affecting vulnerable youth.
Six Feet Deep – Geto Boys
"Six Feet Deep" is a dark and introspective hip-hop song by Geto Boys, released in 1993 as part of their album "Till Death Do Us Part." The track explores themes of death, gun violence, and the harsh realities of street life. Geto Boys' lyrics delve into living in a dangerous environment, where survival is a constant struggle. This is a society where a mother had to bear the psychological toll of her burying her own child.
With gritty storytelling and raw lyricism, "Six Feet Deep" offers a glimpse into the harsh realities of inner-city neighborhoods, where young males don’t know if they would live to see tomorrow. It depicts the desperate measures people living in the hood take to survive and live to see another day.
I Ain´t Mad At Cha – 2Pac Ft. Danny Boy
“I Ain't Mad At Cha" by 2Pac featuring Danny Boy is a heartfelt and reflective track. The song explores themes of losing a friend to gun violence.
2Pac expresses his forgiveness and understanding towards a friend who beats himself up over the death of his friend. The theme of this song makes it one of the best sad rap songs as it encourages forgiveness from the “victim.”
Slippin – DMX
DMX, released “Slippin” in 1998 as part of his album "Flesh of My Flesh, Blood of My Blood." The track delves into DMX's personal struggles, including addiction, trauma, and the difficulties of fame. DMX is always raw on his verses but this track was on another level.
Through his lyrics, DMX reflects on his past mistakes and the constant battle to overcome his inner demons. Whatever one is slipping into, whether it’s slipping into drug addiction, legal drama, family drama, or gang drama this song is for you. Unfortunately, DMX died struggling with some of these issues he tried so hard to get away from.
Robbery – Juice WRLD
"Robbery" is an emotionally charged and melodic sad rap song by Juice WRLD, released in 2019 as part of his album "Death Race for Love." The track explores themes of heartbreak, betrayal, and the pain of lost love.
Juice WRLD's lyrics depict the aftermath of a failed relationship, expressing feelings of sadness, resentment, and the desire for revenge. He could not love again because of the heartbreak he suffered from a previous relationship.
Smile to Keep From Crying – Boosie Badazz
"Smile to Keep From Crying" is a sad rap song by Boosie Badazz, released in 2016 as part of his album "Out My Feelings (In My Past)." The track delves into Boosie Badazz's struggles with life's challenges, including pain, loss, and the weight of his past experiences which includes the gruesome murder of his friend.
Boosie Badazz explores the concept of putting on a brave face by smiling to cover up his pain and cope with the hardships. With its heartfelt delivery and reflective tone, "Smile to Keep From Crying" offers a glimpse into Boosie Badazz's journey of resilience and finding strength in difficult times.
EF U (Easier For You) – Tech N9ne Ft. Krizz Kaliko & Jelly Roll
Released in 2019 this song has a theme of betrayal, heartbreak, and the emotional consequences. It is also about a toxic relationship that ends the other party in a mental health care home. With intense lyrics, you can hear the frustrations and resentment towards individuals who have caused them pain.
This sad rap song delves into issues that those individuals may face, including depression, anxiety, trauma, and addiction. This track tries to emphasize that it is crucial to promote awareness, provide support, and encourage open dialogue for those navigating mental health difficulties.
Song Cry – Jay-Z
"Song Cry" is the most emotionally vulnerable song Jay-Z has ever released. It was released in 2001 as part of his album "The Blueprint." The track explores the complexities of romantic relationships and the pain of heartbreak.
Jay-Z's lyrics delve into his personal experiences, reflecting on past mistakes, regrets, and the consequences of his actions. He accepts that he was the reason for losing the girl of his dreams.
With raw honesty in the song, Jay-Z conveys raw emotions, revealing a more vulnerable side of his persona. The song serves as a heartfelt reflection on the struggles and emotional turmoil that can come after a breakup.
Stray Bullet – Organized Konfusion
"Stray Bullet" is a socially conscious song about gun violence. Organized Konfusion narrates the story from the weird viewpoint of the bullet. Someone pulls the trigger but it is the “bullet” that does the damage of taking a life. This song is about the journey and impact of the bullet.
Organized Konfusion, released this song in 1994 as part of their album "Stress: The Extinction Agenda." The track attempts to tackle the issue of gun violence and its impact on communities.
It paints a vivid picture of the devastating consequences of stray bullets, highlighting the loss of innocent lives and the cycle of violence experienced in the projects.
Suicidal – YNW Melly
The track delves into the depths of YNW Melly's struggles with mental health and his battle with thoughts of suicide. Through introspective lyrics, YNW Melly shares his raw emotions, expressing feelings of hopelessness, pain, and the desire to escape his inner turmoil.
With its haunting tone and vulnerable lyrics, "Suicidal" sheds light on the internal struggles faced by individuals dealing with mental health issues, aiming to raise awareness and foster empathy for those in similar situations. "Suicidal" is an emotionally charged sad rap song by YNW Melly, released in 2019.
Tearz by Wu-Tang Clan
"Tearz" is a melancholy rap song by Wu-Tang Clan, released in 1993 as part of their album "Enter the Wu-Tang (36 Chambers). A sad rap song reminiscing about the death of a little brother who got shot en route a grocery store. The second verse educates us on practicing safe sex, as it is about a friend who lived a reckless sex life and eventually got HIV.
Wu-Tang Clan's lyrics depict the harsh realities of street life, reflecting on the tragic consequences that arise from senseless acts of violence and recklesness. “Tearz” samples the melancholic melody of "After the Dance" by Marvin Gaye.
Tha Crossroads – Bone Thugs-n-Harmony
"Tha Crossroads" is a heartfelt tribute song by Bone Thugs-n-Harmony, released in 1996 as part of their album "E. 1999 Eternal." The track serves as a tribute to the group's fallen friends and also their mentor Eazy-E. “Tha Crossroads” reflects on mortality, loss, and the search for redemption. Bone Thugs-n-Harmony is known for harmonious melodies and tongue-twisting rap style.
The video depicts scenes of mourning and remembrance and a representation of loss, grief, and spiritual reflection. “Tha Crossroad” is an internationally successful song that debuted at number 2 on The Billboard Hot 100. It got the number one spot the following week and spent 8 weeks on the top of the chart.
The Message – Dr. Dre Ft Mary J. Blige and Rell
"The Message" is a tribute song by Dr. Dre featuring Mary J. Blige and Rell, released in 1999 as part of Dr. Dre's album "2001." This song is dedicated to his brother after his death. Dr. Dre struggles with the loss of his brother and was living in denial. He also reminisced over the death of Eazy-E.
They Reminisce Over You (T.R.O.Y.) – Pete Rock & CL Smooth
"They Reminisce Over You (T.R.O.Y.)" is a tribute song by Pete Rock & CL Smooth, released in 1992. The track pays tribute to their friend, Troy Dixon (Trouble T-Roy), who tragically passed away.
With a soulful sample, the song captures a bittersweet nostalgia as Pete Rock reflects on cherished memories and the impact of loss. CL Smooth's heartfelt lyrics and storytelling paint a vivid picture of their friendship, leaving a lasting impression on listeners with its heartfelt tribute and emotional resonance.
This Can’t Be Life” – Jay Z Ft. Beanie Sigel and Scarface
"This Can't Be Life" is a moving sad rap song by Jay Z released in 2000 as part of Jay Z's album "The Dynasty: Roc La Familia." Jay-Z shares personal stories, reflecting on the harsh realities they've experienced.
Scarface “killed” this song with his chilling lyrics about a friend who had lost his son. Scarface received this news as he was about to enter the studio to lay his verse which made him rap about this instead. Jay-Z rapped about his stillborn child while Beanie Sigel rapped about his childhood and drug addiction.
U – Kendrick Lamar
"U" is a track that explores Kendrick's internal struggles, self-doubt, and battles with depression and guilt. This song is full of negativity and darkness. It is primarily about someone battering himself despite his success, he still thinks he is a failure.
The beat switch on this track is “ill”. Kendrick and Jessica used the word complicated 22 times (You can count them) in this song. "U" serves as a poignant reflection on self-worth, personal growth, and the complexities of our experiences as humans.
Uncommon Valor: A Vietnam Story – Jedi Mind Tricks f/ R.A. the Rugged Man
The track vividly depicts the astonishing and harrowing experiences of the Vietnam War which America was involved in. The war involved guerrilla warfare, airstrikes, and ground combat. It resulted in significant casualties and enduring social and political divisions.
Through intricate storytelling and intense lyricism, the artists paint a haunting and horrific picture of the brutality, sacrifice, and trauma endured by soldiers on the battlefield.
R.A. the Rugged Man’s verse is based on a true story, it is a story about his father Staff Sergeant John A. Thorburn’s experience at the war front. As well as highlighting the psychological effects of combat, it also serves as a testament to the bravery and resilience of those who fought in the war.
We Ball – Meek Mill feat. Young Thug
"We Ball" was released in 2017 as part of Meek Mill's album "Wins & Losses." Meek Mill and Young Thug paid tribute to lost loved ones and reflects on the struggles and pain of growing up in challenging environments. "We Ball" serves as a testament to perseverance and the will to overcome adversity while honoring the memories of those no longer with us.
When I’m Gone – Eminem
This rap song delves into Eminem's struggles with fame, and the toll it takes on his personal relationship with his daughter. “When I’m Gone” conveys a sense of vulnerability, self-reflection, and the desire to be there for his loved ones despite the challenges he faces.
The music video begins with Eminem playing a troubled father who struggles to balance his fame with his responsibilities to his daughter Hallie. Em urges his family not to cry for him when he is dead and gone, rather they should find the courage to move on with their life. "When I'm Gone" was, released in 2005 as part of his album "Curtain Call: The Hits."
Dead Homies – Do or Die
Dead Homies starts as a prayer by the late Johnny P. With his harmonic voice, he pays tribute to lost loved ones and friends who have passed away in various circumstances. The lyrics delve into the pain, grief, and remembrance of those whom the group lost to disease, drug use, car crash, and gun violence. With Do or Die’s emotional storytelling, this song captures the essence of loss and the impact it has on the lives of those left behind to deal with the absence.
Smile – Scarface
This is one of the saddest rap songs due to the timing of its release. Scarface released this song after 2Pac’s death, making it Tupac’s goodbye letter to his fans. The music video shows scenes of a drive-by shooting which is the same way in which Pac’s life was cut short. Scarface ended this song with raw emotions while saying a prayer for Tupac in his afterlife.
Final Thoughts on the Saddest Rap Songs

We hope you have enjoyed reading and listening to these songs. They come from the artist’s point of vulnerability, somber or emotional experiences, and it’s aimed at evoking strong emotions and connecting with listeners on a deep level.
After many years of DJing at events, we have played many of the saddest rap songs on radio and at events. This blog post focuses on the most requested and played of them all.
We hope you have enjoyed these and would come back to listen to the songs and read this write-up. Tell us which of these songs you are hearing for the first time. Also, let us know what you would like to read about next.
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