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    The Ultimate Prison ‘n’ Jail Rap Playlist

    Every state and demographic is represented. Welcome to the “land of the free”. The home of hip-hop artists who are brave enough to spit the truth!

    Northeastern Tri-State

    What Up, Kid?

    Nas is a fabulous truth-teller thanks to his natural writing-talent and musical upbringing. “To all my n***** locked up/From Queensbridge and all over!” Nas was inspired after he noticed that there was a repeating phrase at the end of all of his letters from incarcerated friends, “one love”. Nas continues to be one of the best hip-hop lyricists of all time, this is epistolary writing!

    I Hear Ya Prayers!

    “Convicts think they alone but if they listen close/They can hear me groan touch the wall feel my pulse!” Nas skillfully conveys the terror of prison by bringing a cell to life. He paints a picture of imprisonment being almost worse than death as imprisonment becomes personified by Nas’ portrait.

    You Can Hear The Roar!

    New York City imagery abounds as Kool G Rap appeals to the hearts and minds of the city’s youth. “Don’t ever get caught in a crime my friend! ‘Cause this bus trip is not to Adventure’s Inn!” Kool G Rap speaks truth to power. 

    Without No Bail!

    “I fell asleep with my face in my plate/And the next thing you know, I was headed upstate!” Catching a bid over being overweight is rotten luck, but it is an amusing topic to write a song about! According to, “Ego Trip Magazine listed this track as one of the greatest singles of 1984.”  

    Holdin’ It Down!

    There’s never a reason to not be on the grind. “I hit the law library, hope to come home soon!/I just finished up the album, fin’ ta drop in June!” No matter where you do it from, work is work! Capone n Noreaga hype each other up because life ain’t easy.

    Real Rock From The Rock!

    Chuck D. refuses to join the military because he’s a Black man. “I could never be a veteran!” To make matters worse, the now-criminal also refuses to stay put in prison.

    Whole Feelin’ Was Foul!

    According to, “the low level of swearing suggests that he wanted this song to be taken seriously”. “I’m a warrior! I got my ground to hold!” This is a relatable point of view tale.

    The Line To Walk

    According to, “The title is a reference to the legal concept of Habeas Corpus, which is the right to be informed of the reason for detention”. The hook is brutal! “I found love on a prison ship!”


    “My spirit start to deflate, ‘gotta live with this one mistake!” Casanova battles dark thoughts on this somber track. He also battles with the cyclical nature of generational trauma. It’s heavy stuff.

    No Longer A Rebel

    According to, the leader of the rap group is Maxwell Melvins. His prison number was 66064. Another rap attempt to intimidate the next generation into being good citizens.

     Payback’s A ************

    This song paints a vivid picture. Inmates must do things they don’t want to do in order to survive. “Gotta sh*t in your palm”. It all sounds so unpleasant!

    Why You Cryin’?

    “Life is so unfair!” Sometimes expressing a harsh reality makes it easier to cope with that reality. This explains why the same prison themes continue to recur throughout the decades. The reality never changes, but the inmates do.

    A Little Tale About This Jail Stuff

    “This type of sh*t happens every day!” According to, “This song contains vocal samples from three songs; Living for the City by Stevie Wonder, ‘Top Billin’’ by Audio Two, and ‘La Di Da Di’  by Slick Rick & Doug E Fresh.” Maybe that’s why this jam is iconic.

    They Won’t Let Me Out

    “I’m locked up!” What else is there to say? reports, “countless thousands of convicts have declared that this song gave them peace, solace and a sense of kinship while they were serving time in prison”.

    I Used To Be A Lonely Man

    “They don’t know what the f*ck it’s like to be so fed up! And fed so many uppers”. Sometimes prison is a metaphor. Rappers can sometimes feel “imprisoned” by shoddy management or a predatory contract.

    West Coast

     My Eyes Are Closed

    “It’s gonna take a miracle they say!” Snoop Dogg must have gotten his miracle. The legend is still sippin’ and smokin’ on the outside to this day.

    Dear Mama

    According to, “[2Pac] was a mirror of [street] society, and was able to put it into words like no other”. They got you trapped, you’re better off gettin shot/I’m convinced self-defense is the way!” 2Pac was writing with the collective in mind, but his own negative thought-patterns ultimately contributed to his untimely death. 


    “Nowadays snitches run the penitentiary!” This song is chilling to the bone. Then again, it might be comforting when forced to endure the torture of solitary confinement!

    Prison Of Seclusion

    The music video for this 1991 song was released at around the same time as when 2Pac was assaulted by the police. Talk about life imitating art! “They got me trapped!”

    The South

    Inmate, Lost From The Shell Shock

    What do civil rights mean when so many American citizens have been stripped of them? Ludacris isn’t afraid to call out false promises. “I’d dream that I could tell Martin Luther we made it/But half of my black brothers are still incarcerated!” 

    I Wish That I Could Rewind

    “Years that I won’t get back!” It’s terrible hearing young rappers regretting life choices. Kodak Black highlights a universal truth. Life is too short, that’s real. 

    I Farted In The Cell

    “Just got out of jail. Just went back to jail!” The Gucci Mane-centric lyrics explain the cyclical nature of prison bids. says the song, however, is a “parody”.

     Tell Ya Old Man

    “I ain’t goin’ back to jail and that’s what these suckers fear!” Will-power at its finest! These bars go hard. 

    Like Livestock

    This song is from 2015, but it has lyrics as thoughtful as any old-school jam. “I ain’t got a lawyer, I don’t need one!”

     Great Health, Cheers To That

    “You motherf*ckas better get free!” Everyone makes mistakes. Life is all about accepting them and moving on.

    I Questioned Devils

    This new-school rapper heeds the advice of elder rappers. Despite his current circumstances, NoCap is choosing to carry himself with pride. “My head high doing jail time!”

    Bread That Is Stale

    It is unclear if Shaggy is discussing a prisoner in his homeland of Jamaica or in his adopted state of Florida. That is because the treatment of prisoners around the world is unfortunately atrocious. “Man them beat him with the baton, read him personal mail!”

    The Midwest

    Priors, Priors

    According to, this track “serves as the beginning of DONDA’s narrative structure. We find Kanye in the midst of a crisis, spiraling out of control as his marriage falls apart and his public image falls apart once again.” Jay-Z’s verses illustrate the behind-the-scenes friendship reunion. “Told him, ‘Stop all of that red cap, we goin’ home!’ Not me with all of these sins, casting stones!’” 

    Heroic Songs Unsung

    “Since slave days separating fathers from children!” According to, Common won his first Emmy Award for this song. He “dedicated his award to all incarcerated people in the prison system and justice.”

    This Guy Who Slashed Me

    This rap song describes being the victim of a crime. “He then slashed me in the face, and then in the back!” Justice is actually served in this track at least. 

    Do you associate rap music with prison? What can rappers do to advocate for prisoners and prison reform? Let us know by leaving a comment!


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