Let’s Get Free: Hip-Hop Prison Breaks

Today is the 20th anniversary of Nelson Mandela’s release from a South African jail, after 27 years in prison. In the spirit of Black History Month, I wanted to highlight that moment in time, but with a hip-hop twist. Rappers are far from political prisoners, but we’ve heard enough “Free RAPPER NAME HERE” T-shirts to know what it’s like to anticipate a jail homecoming. Here are some of the most memorable prison releases (in chronological order) of hip-hop’s incarcerated Scarfaces. —Rondell Conway

10. SLICK RICK – January 1996

The Ruler’s Back!
Serving time for shooting at his cousin during a family dispute, ’80s rapper Slick Rick was transferred from prison into a work release program in 1994 and worked on his third album Behind Bars. Two years later he was out of work release and officially a free man.

9. 2PAC – October 30, 1995

Check Out Time
As the legend goes, ’Pac was free on parole after serving eight months of a four and a half year sentence for sexual assault. The controversial rapper left New York’s Clinton Correctional Facility and headed straight to the studio to record his multi-platinum Death Row debut, All Eyez On Me.

8. T.I. – June 21, 2004

Party Crasher
Fans in attendance at ATL’s Hot 107.9′s Birthday Bash concert got a pleasant surprise when T.I. burst on stage to cheers from his hometown crowd and sparked his much talked about beef with Houston rapper Lil Flip. At the time everyone thought Tip was still in jail for parole violation. Little did they know the King was fresh out the joint when he made his way over to the show to get a few things of his chest.

7. BEANIE SIGEL – August 9, 2005

State Property No More
The Philly MC was released from Federal Correctional Institution of Fairton, New Jersey, after serving a year and a day on gun charges. Beans was welcomed home by a mob of friends and family led by Dame Dash. The then Roc-A-Fella CEO presented Sigel with a State Property gift box, which included a DVD copy of State Property 2 (Sigel starred in the flick, but never saw it), some State Property gear and a pair of sneakers from Sigel’s State Property shoe line. Ha! Oh, the irony in it all is just too much.

6. PIMP C – December 30, 2005

Big Pimpin’
The release of the Houston rapper brought an end to the widespread “Free Pimp C” campaign. Pimp, one half the veteran rap duo UGK, was incarcerated for three years on an assault charge. Wonder what everyone did with their “Free Pimp C” T-shirts?

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  • Slangeditor

    “It’s always sad seeing your favorite raper get locked up…”

    “Raper.” Bwahahahahaha.

  • Southsider


  • Mr. North

    You forgot Project Pat who got locked up around the same time as Pimp C for a parole violation, did 3 years. Mister Don’t Play went platinum while he was in jail like 2Pac did.

  • http://www.bboycult.com The $ykotic Don Mac

    …and now I see what dudes say about the regional bias…Rondell do you actually do research or are you going off the top?

    GHOSTFACE KILLAH (too young to know???)

    OLD DIRTY BASTARD (I’m going off the top, should be #2A)

    co-sign FLESH N BONE

    co-sign PROJECT PAT

    RAS KASS (some people actually like his music)

    TONY YAYO (was a BIG movement)

    DMX (the bloggers couldn’t wait)

    STYLES P (you don’t remember???)

    co-sign LORD INFAMOUS

    The next big one on the come-up:PRODIGY

    C’mon son…

    • AZ40

      i think he did an okay job of pickin’ people from all over, but yeah how could he forget styles p, he actually did a crime not just violate parole

  • HU

    C’mon Man! Co-sign Flesh N Bone.

    On another note:
    How can you blame whites for being racist after looking at that Gucci Mane picture? I hates blacks too now.

  • mat

    GHOSTFACE KILLAH, ODB, Bg knocc out!!

  • TheR

    Free P, Prodigy hold your head

  • daydeezy

    speaking of JAIL whats up with “Brutha Lynch” the nucca that ate his girlfriend “not out” but ate her…lol

    • North

      That was Big Lurch.

      • 619

        Big Lurch is in solitary in prison in Sactown. It wasn’t his girl that he killed, it was his homeboy’s girl.

  • daydeezy

    My bad I mean ” Big Lurch” …

  • http://xxlmag.com Ben

    What about Mac Dre? He stayed going to jail, served a 5 yr bid on some bank robbery shit.

  • Aaron

    how ya’ll forget about c-murder?

  • Dopeman1

    Damn!!! You forgot about John Forte

  • caino

    we didnt forget C-Murder, we just dont talk about his stupid Ass !! lol

    But yeah Big Lurch is a monster, dude had like half her lung in his stomach!! you see rappers today going to jail just dont put in the commitment like they used to ! lol

  • http://www.uctf.com Jamal


  • General

    Agree with a lot on here. I don’t know how the hell you missed Flesh N Bone…Oh well…

    Also I know you tried to backtrack after you said it, but even putting Nelson Mandela’s name in the same sentence with the plight of these idiots that lost untold amounts of money because of their ignorance is probably the most ridiculous thing I have seen on the site in some time…

    I really hope ya’all are doing whatever possible to keep Bol happy with working on this site because if you haven’t noticed a lot of commentors are jumping ship lately…

    Shout out to Grands

    • http://www.bboycult.com The $ykotic Don Mac

      Gen whats good?

      capcobra where you been?

      Grands is doing the damn thing over @ daily-math w/Combat Jack and thetonygrands.wordpress.com

      dallaspenn.com for the homie Billy X

      I’ma start devoting more time to bboycult.com

      You’ll see the homies…

      • NotoriousAGC

        man tony grands got some small ass letters in his page, but liked the john mayer post more than bol’s

  • heartlandG

    Dat ni99a said Brotha Lynch ate somebody!? Im like wtf!? ((coppin dat new album too))…ne who aint herd of “Big Lurch”, Free Boosie Bad Ass!!! …What happin to JT Money (who dat who dat who dat who dat whooo…) AND Drama (left left left left left right left…)

  • capcobra

    what about capone and cormega?

  • Jhon da Analyst

    Ras Kass is the best ever!!! @$yk

  • gzer69

    Big Tray Dee

  • lol

    What about whats his face cassidy did he not go to jail and come out for a shooting or am I wrong?

  • Abdul Sosa

    shyne culda joined the top 10 if he didnt go to jail
    and he deserves to be #1

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