10 Best Rappers To Drop Albums While In Jail – Penitentiary Chances


Pimp C The Sweet James Jones Stories (2005)

While Chad “Pimp C” Butler made his mark as one-half of the beloved rap duo UGK, his solo debut was marred in controversy. In 2002, The Pimp was sentenced to eight years in prison for violating his probation, which he received as a result of a previous aggravated gun charge. With the “Free Pimp C” campaign in full swing, UGK’s label Rap-A-Lot Records dropped Pimp’s debut The Sweet James Jones Stories in 2005. It was an album filled with older, previously unreleased material, placed over new beats. With little to no promo, the LP remained largely overlooked, but Butler was redeemed in 2006 when he was released from prison and dropped Pimpilation.


C-Murder The Truest Shit I Ever Said (2005)

Convicted of second-degree murder in the death of a 16-year-old fan, C-Murder recorded this entire album from prison on his lawyer’s hand-held recorder. After releasing a disc every year from 1998 until 2002, this was his first solo project since the 2002 shooting. The Truest Shit… was unable to achieve the mainstream success of the No Limit soldier’s first three releases, each of which landed in the top 10 on the Billboard Top 200, but it did hit No. 1 on the Top Independent Albums chart.

A video for the lead single, “My Life” included footage of C-Murder in jail, as well as clips of people on the outside rapping his lyrics and wearing commemorative T-shirts. This album may have been the truest shit he ever said, but the smartest shit he ever did was changing his moniker to C. Miller during a 2009 trial.

  • Teddy

    whoever didnt vote 2pac kill yo self

  • spm

    Im from houston and when spm got locked up he was just starting to have some cross over success, so he had a decent amount of fans. Also, houston has alot of hispanic people and hes problably the most famous hispanic rapper at the time, especially from houston, and he had alot of hardcore fans. fans already buy gangsta rap albums from a prison guard (rick ross) and r&b albums from men who do terrible things to young girls (r kelly & chris brown)

    • El Tico Loco

      Guess SPM is no exception look how he got more votes than Slick Rick, Shine, and Pimp C.

  • Sha

    Tupac. No doubt.

    But I would love to see a new list.

    How about, THE TEN SMARTEST RAPPERS WITH NO JAIL TIME OR FELONIES.

    Now that’s a hard list to compile.

    • robmarkman

      haha Talib Kweli LOL

    • zac

      1. Jay – Z
      2. Eminem
      3. Birdman
      4. Gudda Gudda
      5. Nicki Minaj
      6. Twista
      7. T-Pain
      8. Nelly
      9. BlokzZ
      10. All Members of Hilltop Hoods

  • Eddie Blanco

    THUG LIFE BITCH!!!!!!!!!!!

  • Anonymous

    HAHAHA LOOK AT THE PIC OF LIL PUSS WAYNE!HE LOOKS LIKE HE WANTS TO CRY!HAHAHA I GUESS THATS HOW BLOODS DO IT HUH

  • SuperFLY

    Here goes XXL again riding lil’ waynes dick… XXL must be ran by 17 year old girls or somethin’.

  • Kenny D

    Who were the 31 idiots who voted Gucci Mane? Probably a bunch of girls. Everyone knows Pac was best hands down. Me against the World was his best album PERIOD!

  • PROVIDENCE DONN

    Ya niggas missed Keith Murray, that shit he dropped when he got locked was official. I don’t remember the exact name of it but it was some shit like the first . THe most beautifullest something. That shit was tight though

  • caino

    Cant believe u have SPM on this shit!!

  • nasjiggapac

    pac no contest ! only hoodrats and dumb niggas voted for cucci mane

  • Dick B.

    Hahaa I knew some people thought Gucci is better than Pac. Are we voting for the best album or rapper though? Either way it’s Pac.

  • Jon Dog

    XXL, grow the fuck up already!

  • Q461

    I gotta say 2pac. That album is also probably his crowning achievement. Def a classic.

    Crazy how jail fucks with cats careers though.Slick Rick’s first album was a classic. He has had a brief career, but is still one of the greats. Imagine if he had more records. Shyne’s career sidelined 10 years during his bid.

  • Anonymous

    Khadafi dropped “Lethal Weapon” with Trez while locked up, also “The Death Of Tragedy”. Plus Prodigy dropped “HNIC 2″ and “Product Of The 80′s” and hes still locked. These 4 albums SHIT on all these other lames careers, easily. And Khadafi KILLED “War Report” but XXL dont mention him cuz XXL a buncha suits chasin fame.

    • http://xxlmag jayruckNYC

      Cosign. Trag MADE that album. Just listen to CNN hooks since then. Listen to the hooks on Against All Odds or Thug Matrix. Trag definitely had a huge hand on what The War Report became. For some reason Trag don’t get credit but CNN ain’t been the same since he left.

  • TicNitty86

    Why even talk about some ig’nant azz crap like this?

    Half those mofo’s have no true talent anyway.

  • TicNitty86

    Why even talk about this ig’nant azz crap?

    Half these mofo’s have no true talent anyway…

  • http://xxlmag jayruckNYC

    I only looked at the list to make sure Beans was there. If dat album wouldnt have been on the list XXL would have dropped the ball big time. Pac gotta be number one on this list. Me Against The World to me is Pac best album. None of that shock value east/west bullshit just real songs. Gotta love it. Beans gotta be a close second tho. The War Report third and Slick Rick fourth. I’m surprised Gucci is gettin so many votes. lol

  • Darth H8ter

    Yuck, SPM i sa sick individual if his Wikipedia page is to be believed.

  • loyal 2 tha game

    whoever voted gucci instead of pac is obviously young ass underaged cats ‘new 2 tha game’ 4real . .

  • http://www.youtube.com/watch?v=-nz77ATFVhs&feature=player_embedded Smooth Operateur

    This vote makes me happy. At least 2Pac gets its right due comparing to Gucci Mane. Me Against The World is the only “work of art” among those albums. Pimp C, C-Murder, Shyne’s albums have all been fabricated while they were absent so they can’t really be counted as a proper work. CNN’s was a cool album but Capone was only one of the ingredients. Beanie Siegel should come 2nd…

    There are plenty of undergound rappers like SPM who were in jail and dropped albums, so why talking about him especially, trying to look like you know underground music????

    OH, AND WHAT ABOUT C-Bo (I can’t remember how many times he was in jail while dropping great albums) and Z-RO? “The Life Of Joseph Mc Vey” and “Still Livin” should be just behind “Me Against The World”, but, like someone said, XXL’s writers are 17 years old girls lol

  • nishan

    tu pac the real only rapper till now no bullshit and every thing true what the fuck all ya knew about pac shit nth listen to his cronic album and all of his song ya al know who was iridgt and who was wrong me frm nepal may be the most of u neva heard thename of ma country but me frm so far i know how rue he was if he had been alive yo nigga no one should be twistd in the game no after math chain he should have stopped it unfortunately he stood in path he died because for all of u nigga

  • thizz mountain

    the fact that mac dre isnt number 1 or even up there just shows how hard ur fuckin up