A History of Freestyles From Jail

From Max B to Lil Wayne, check out these memorable rap moments through the wire.

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Complex Original

Image via Complex Original

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Rappers have a long history of getting into the trouble with the law. For most of them, this typically ends with doing hard time, a result that can hurt the momentum of their career. But being behind bars can't stop the hungriest of rappers from doing what they were born to do, even if it means delivering rhymes over the phone.

Rapping freestyles through the wire is nothing new, with MCs like Mac Dre to Lil Wayne dropping bars for public consumption. Even a select few, like Sacramento rapper X-Raided, have recorded entire projects over the phone. Pretty wild. As a refresher, let's go down memory lane and take a look at A History of Freestyles From Jail

RELATED: The 25 Realest Rap Songs About Prison 
RELATED: Lord Is Tryna Tell You Something: How Charly Wingate Became Max B 
RELATED: Locked Up: When Rappers Release Albums From Prison 

Mac Dre

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Title: "Back N Da Hood"
Date: 1992

While doing a stint in Lompoc for refusing to cooperate with the police, Bay area rapper Mac Dre recorded an entire album over the phone called Back N Da Hood. Some of the material that didn't fit on that EP made it onto a project he would complete later, Young Black Brotha: The Album. As if recording a body of work behind bars wasn't admirable enough, the rapper also got his G.E.D and taught another inmate, fellow Cali rapper X-Raided, how to record over the phone.

X-Raided

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Title: "Unfukwitable"
Date: 1995

Incarceration usually puts a damper on most rappers' musical progress. For West Coast rapper X-Raided, it had the opposite effect. Currently serving 31 years to life for a gang-related homicide, the rapper has managed to create a stunning 20 albums behind bars, in addition to securing a deal with Empire Distribution. Among the first of his clink-recorded masterpieces was Xorcist, which featured the song "Unfukwitable."

Supa Nate

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Title: "Nathaniel"
Date: 1998

OutKast showed love to their close friend Nathaniel Elder, aka Supa Nate, by including his prison freestyle on their critically-acclaimed album Aquemini. Nate's deep rhymes along with his Southern twang revealed just how talented he was. Probably not the limelight experience he had hoped for, but what are you going to do?

Mysonne

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Title: N/A
Date: 2003

New York rapper Mysonne found himself behind bars in 2003, where the former Violator signee showed off his lyrical ferocity in a phone call freestyle. Unfortunately for him, this is probably up there as one of his career highlights.

Hell Rell

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Title: "Hell Rell (Interlude)"
Date: 2003

Hell Rell took the idea of an interlude to the next level with his jailhouse freestyle on Diplomat's Diplomatic Immunity. While Rell is relatively seen as a lesser member in the crew, he dropped some pretty slick rhymes that displayed his worth, at least for a minute or two.

Shyne

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Title: "For the Record"
Date: 2004

Shyne dissed 50 Cent in a freestyle while serving time at Clinton Correctional Facility in 2003, where the Brooklyn rapper was locked up from 2001 to 2009 for the infamous shooting incident involving Puff Daddy and Puff's then-girlfriend Jennifer Lopez. The diss was a response to 50 calling Shyne "soft." 

Tony Yayo

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Title: N/A
Date: 2004

Tony Yayo was sadly absent during G-Unit's early success due to him being incarcerated from 2003 to mid-2004 for a number of charges. How did he keep his name ringing in the streets? By rapping from prison, of course. Recorded at the height of 50's beef with Ja Rule, Yayo shared a vicious freestyle directed at Murder Inc. members Ja, Ashanti, and Irv Gotti, and donned himself the "Murder Inc. killer."

Cassidy

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Title: "Jailhouse Boogie"
Date: 2005

Cassidy's stint in Philadelphia's Curran-Fromhold Correctional Facility back in 2005 yielded "Jailhouse Boogie," a freestyle that was later made into a record for The Hustla's Home mixtape thanks to Big Mike and DJ Thoro. 

Max B

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Title: "Sharing's Caring"
Date: 2009

Max B's "Sharing's Caring" freestyle from prison in 2009 was a gift that fans should appreciate. The possibility of hearing legitimate new music from Max B is pretty much a wrap at this point as Charly Wingate is in his fifth year of a 75-year sentence for a myriad of charges, most notably conspiracy to murder.

Kevin Gates

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Title: "Freestyle Live From Jail"
Date: 2009

In 2009, Kevin Gates released his mixtape Behind Enemy Lines, the intro of which was a freestyle the Baton Rouge native recorded while in jail. His commanding voice sliced through the static of the phone call, making the listener feel his pain behind bars. 

Prodigy

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Title: "The Phone Tap (Welcome to State Prison)"
Date: 2010

Prodigy kept it all the way real in 2010 when he rapped a freestyle from prison, which would later be added to Sid Roam's sinister production. P spent nearly seven minutes dropping bars about his disdain for current acts at the time, even sending shots at Kanye West and Saigon.

Gucci Mane

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Title: "Burrrprint 2 HD Intro (Live From Fulton County Jail)"
Date: 2010

Gucci Mane always seems to find himself in trouble with the law. Still, his time behind bars never hampers his productivity. In 2010, the Atlanta rapper spit some bars over the phone that would later be used for the intro track of his mixtape Burrrprint (2) HD.

Lil Wayne

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Title: "Light Up Freestyle"
Date: 2010

Lil Wayne was locked up for the majority of 2010 after pleading guilty to attempted criminal possession of a weapon, which meant he was absent during the promo run for Drake's debut album Thank Me Later. Weezy more than made up for it by spitting some bars through the wire to Drake's "Light Up."

Bump J

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Title: "Live From the Feds Freestyle"
Date: 2010

Bump J rattled off a freestyle at a federal prison in Big Springs, Texas, where the rapper currently lays his head after pleading guilty to a bank robbery that took place in 2007. The once-prodigal son of the Windy City proved he hasn't lost an edge lyrically. Keep your head up, Bump.

Remy Ma

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Title: N/A
Date: 2010

Remy Ma kept her name buzzing in 2010 with a freestyle that took place at the Bedford Hills Correctional Facility for Women. It was six minutes worth of rhymes that die hard fans probably know by heart, considering it was all the music Remy had at the time. They can expect more, though, as Remy Ma will be released soon.

Turk

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Title: N/A
Date: 2011

Turk got his a capella on in prison while serving a sentence for second-degree attempted murder back in 2011. The freestyle itself was so-so, but it was clear Turk was hungry to get back on the microphone. And he would, a year later, when he was finally released.

Young Buck

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Title: N/A
Date: 2012

While serving an 18-month bid in Southern Mississippi at Yazoo City Medium Security Federal Prison, Young Buck dropped a few bars during a phone call with his friend Charlie P. Buck was going through financial setbacks at the time, but he still kept it positive with boastful rhymes of his street legend. Now back with G-Unit, Buck is flourishing once again.

Young Scooter

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Title: "I Wonder"
Date: 2013

A six-month stint in Dekalb County Jail couldn't stop Young Scooter from feeding the streets back in 2013, who released a song called "I Wonder" that featured recorded verses straight out the pen. He even shared a handwritten letter that highlighted his appreciation for fans that supported him. And they don't have no award for that.

J.R. Writer

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Title: "I'm Done Talking: Live From Ulster Correctional"
Date: 2014

No one can say for certain where the resurgence in public interest for Dipset has come from in the past year or so, but not everyone has received their fair share of love. J.R. Writer is one of them, and after the "Dipshits" video from Cam'ron dropped, Writer didn't let his jailbird status stop him from airing his grievances. He spit a freestyle that featured some disparaging lines toward Jim Jones and Cam'ron: "Do he still fuck with Cam? Do he still fuck with Jim?/If niggas turned their back on you would you still fuck with them?"

B.G.

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Title: "U.O.E.N.O. Freestyle"
Date: 2014

Back in late '90s, the Hot Boys were almost untouchable. On the other side of '05 though, Lil Wayne's ascent to stardom dwarfed the achievements of its other members. Truth be told, updates on any of them that aren't related to criminal activity have been few and far in between. Still, hearing B.G.'s same Southern twang from a decade ago ring out on an instrumental that is very much 2014 (Rocko's "U.O.E.N.O.") almost gives you hope for the future. Or it just makes you incredibly sad, depending on how long you think about his 14-year prison sentence for gun possession and witness tampering.

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