2Pac To Troy Ave: 14 Rappers That Saw Jail Time Help Or Hurt Their Careers [VIDEO]

2Pac is one of the most influential rappers of all time, but not just for his lyrics and image. It’s also because many rappers after him have tried to emulate the success he achieved due to going to prison.

In 1995 2Pac made history when he went to prison on rape charges and released Me Against The World, an album that debuted number one on Billboard and went on to sell two million records in a year. The feat made 2Pac the first artist to have a chart-topping, platinum-selling album while serving time behind bars. He made history again the next year when he got out of jail and released his double-album All Eyez On Me to rave reviews and even more platinum plaques. To this day the album is known for its hard-ass opening “Ambitionz Az A Ridah” with Pac making sure that the first time you heard him out of jail was going to be him at his best. It’s also known for the “out on bail, fresh out of jail” line on the first single “California Love.”

Rappers have been trying to capture that lightning in the bottle ever since. However, it must be noted, jail time rarely translates into platinum albums and critical acclaim, if ever at all. But, that hasn’t stopped rappers from trying to capitalize off going to jail. Try deciding for yourself if going to jail hurt or helped these rap careers.

Photo: Screenshot

Shyne

Perhaps the only rapper other than Pac to see jail “help” his career is Shyne. Jail time was swirling around his music before his debut album was even released. He signed to Sean “Diddy” Combs’ Bad Boy Records in 1999 and appeared on a couple of the label’s artists songs and remixes, immediately drawing comparisons to The Notorious B.I.G. because of his voice. But later that year he was involved in the infamous Manhattan club shooting where he allegedly opened fire in a club after someone threw money in Diddy’s face. He was subsequently charged with attempted murder, assault, and reckless endangerment. His self-titled debut album dropped in September 2000 and almost went platinum. But the celebration was short-lived as he was sentenced to 10 years in prison in July 2001. In 2004, after a bidding war between labels salivating to sell Shyne and his street cred, he reportedly signed with Def Jam Records for $3 Million. The album Godfather Buried Alive, was mostly recorded before he went to prison but featured one song recorded from behind bars. The album featured production from Kanye West, Swizz Beatz, Irv Gotti and Just Blaze and nearly went Gold, debuting at #1 on the Billboard Rap Charts. Shyne never released another album. He was freed in 2009 and deported to Belize. He has only released one mixtape, 2014’s Gangland, since.

Verdict: HELPED. Shyne defied Monopoly logic and collected $3 million dollars for GOING to jail.

Slick Rick

Slick Rick predated 2 Pac as far as rappers releasing music while in jail, but this part of his career is often forgotten. Rick went to jail in 1990 after he shot an innocent bystander and his cousin/bodyguard who he says was extorting him and acting on threats to take his life. Russell Simmons bailed him out and Rick spent his brief time out rushing to record The Ruler’s Back that was released in 1991. Rick was eventually sent to prison to serve five years for attempted murder. In 1994 Def Jam released Rick’s third album Behind Bars while he was in jail. Rick got out jail in 1997 and spent the next year or so recording his 1999 comeback album The Art of Storytelling. Since then Rick has been making the rounds on the old-school Hip Hop concert festival.

Verdict: HURT. Slick Rick went into jail as a rising star. But with rap moving so fast, by the time he came out he was already considered “old school.”

T.I.

No time is ever a good time to go to jail, but T.I. has always managed to find the absolute worst times to go. In 2004, right when he was starting to live up to his self-appointed “King of the South” title with his hit single “Rubberband Man,” T.I. was nabbed for parole violation and sentenced to three years in jail. He served one year of the sentence and immediately got back to work by engaging in and prevailing in a rap beef with Lil Flip in 2005 and then releasing his classic album King in 2006. T.I. would ride the wave of success for about year until he found himself in trouble again when he was arrested just blocks away from the BET Hip Hop Awards in Atlanta where he was caught trying to buy some guns in a parking lot. He was ordered to house arrest after paying a $3 million bond and was eventually sentenced to 366 days in prison. In the time leading up to serving the sentence he recorded verses for Yung LA’s “Ain’t I” and Mary J. Blige’s “Good Love” referring to his impending sentence a hosted a farewell concert in Atlanta. When he got out he seemed to be doing better than ever releasing the biggest album of his career, Paper Trail, landing high-end endorsements and movie roles. He started recording a new album to be titled King Uncaged, but in September 2010 he and his wife Tiny were busted for drugs in Los Angeles and was sent back to jail for 11 months. Before he went in he changed the title of his album to No Mercy. The album went Gold but got mixed reviews. T.I. would again get out of jail in 2011 and he hasn’t been back. Since then he has released two chart topping albums, went independent and became a shareholder in Jay Z’s Tidal.

Verdict: HURT. T.I. continues to bounce back but lawyer fees rack up after while. His constant returns to jail slowed up his Grand Hustle label to the point that artists on the label weren’t releasing records and forced him to restructure the company multiple times.

Lil Wayne

In 2007, Lil Wayne got bammed on some trumped up weapons charges for essentially being on his tour bus, sitting next to a bag that had a gun in it that was not his. Reminder, 2007 was in the middle Weezymania as he was the biggest name in rap at the time, and it was a year prior to his biggest album The Carter III hitting stores. The charges would loom over Wayne’s head for years before he was actually sentenced in 2010. In that time though Wayne continued showing his super-human abilities dropping mixtapes and recording songs and videos to keep his name hot while he was away. His rock album Rebirth dropped just one month before Wayne started serving his sentence and it got mixed reviews. Cash Money would release another album, I Am Not A Human Being, while Wayne was locked up and it wound up becoming the first #1 Billboard album from an incarcerated artist since 2Pac’s Me Against The World. Wayne wound up serving less than a year in jail but in that time his protoges Drake and Nicki Minaj began coming into their own. His first album out of jail, 2011’s The Carter 4, broke iTunes download records and would go multi-platinum.

Verdict: Hung Jury. Lil Wayne going to jail didn’t seem to have any real impact, good or bad, on his career.. His albums continued to sell and he hit the ground running when he got out. The most that can be said is that Wayne hasn’t released another official album since Carter IV.

Boosie Badazz

When Boosie was headed to jail in 2009 he actually thought he had struck gold. Knowing he was facing at least two years jail time on marijuana charges, Boosie was out promoting his album Superbad. In interviews before he set to turn himself in, Boosie said that he thought jail time would help his career, adding to his mystique and hoped to sign a big record deal once he was released. Superbad was released on September 15 of that year and he turned himself in a week later. What was initially a two-year sentenced turned into five years after a judge tacked on a first-degree murder charge and more time after Boosie was allegedly caught trying to smuggle drugs into prison. During his incarceration his label home Trill Entertainment released the album Incarcerated to mixed reviews. Boosie was found not guilty on the murder charge but he still had to stay in prison until 2014. Boosie was released in March 2014 to much fanfare, media hype, a press conference with Angela Yee and outrageous “Boosie Mandela” t-shirts. He would release Touch Down 2 Cause Hell in May 2015, but hardly an of those “fans” screaming “Free Boosie” supported it. Despite positive reviews, the album sold around 78,000 in its first two weeks of release. But, if Boosie’s Instragam posts are any indication, life is good.

Verdict: HURT. In the time Boosie spent locked away artists like Kevin Gates, 2 Chainz and other essentially took over the Hip-Hop chitlin circuit that he helped create and parlayed it into superstardom and chart topping hits. Boosie is now playing catch up.

C-Murder

https://www.instagram.com/p/BGtqRcGGj2h/?taken-by=trucmurder

C-Murder has released more solo albums from prison than he did when he was a free man. Since 2005’s The Truest Shit I Ever Said, C-Murder has been recording and releasing music while either being on house arrest or locked up. While he still manages to find the resources to get beats and release the music, not much of it has made a dent since his 2008 single “Get Fresh.” Actually, the only time C-Murder’s music has made the news is when people [including prison officials] ask how he finds a way to make it. He’s actually under investigation right now after he released an album with Boosie Badazz titled Penitentiary Chances in April with a video for the song “Dear Supreme Court.”

Verdict: HURT. C-Murder is still locked up.

Beanie Sigel

Beanie Sigel all but predicted the fate of his career when he created the State Property brand to promote a jail clothes inspired clothing line, release compilations titled The Chain Gang and make a movie about him going to jail. At the height of his career he was debatebly the second most popular artist on Roc-A-Fella Records behind Jay Z, the other being a young Kanye West. With Jay Z retiring from rap, the stage was set for Sigel to move in the ranks. But starting in 2002 with a weapons charge, Beanie just started wilding out. In January 2003 he punched a 53-year old man and broke his eye socket. In July of that same year he was charged with attempted murder, aggravated assault, simple assault and possession of a criminal instrument after allegedly shooting up a club injuring two people. He escaped the attempted murder charges [he rapped about being offended by the charge because it “disrespected his aim“] but he did wind up serving one year in jail over the previous weapons charge. In the time leading up to serving his sentence, Sigel was working on his third album The B.Coming. The album would come out in 2005 while he was in jail and of course, he was on the cover behind bars. The album was arguably his best work, but he wasn’t there to promote it or bask in the acclaim. Adding insult to injury, Roc-A-Fella Records’ founders Dame Dash and Jay Z split while he was locked up. Sigel got out jail in 2005 but went right back months later after falling behind on child support. Finally, in 2007 he released his welcome home album The Solution, but the rap climate had changed by then with snap/trap/dance tracks dominating the airwaves. When he got of jail for that he was shot and robbed a month later. Sigel would continue to release music but to less fanfare without the Roc-A-Fella affiliation. In 2010 he was charged with failing to file tax returns. He was scheduled to start serving his two-year sentence on September 12, 2012 but he expedited the process by getting caught and arrested with drugs and guns on August 29. This was just days before he was expected to join his former Roc-A-Fella teammates at Jay Z’s Made In America festival in his hometown of Philadelphia. Beans got out of jail in 2014 and has been doing shows and festivals here and there. He is scheduled to perform at a State Property reunion show on June 12.

Verdict: HURT. From the time he recorded “What Ya Life Like” on his debut album, jail has been a part of his life just as much if not more than music.

Gucci Mane

Sometimes it’s hard to say Gucci Mane’s name without throwing “free” in front of it. Jail is probably the only place that Gucci has spent more time in than the studio. Being incarcerated has been a part of his career since it started. Shortly after his debut album Trap House dropped Gucci was ambushed by a group of men and he killed one of them in self-defense. When police issued the murder charges he was in New York shooting an episode of BET’s Rap City. Under advice from his lawyer, he left, flew back to Atlanta and turned himself in. Upon his arrival at the DeKalb County jail, his then label Big Cat Records seized the opportunity for publicity by parking promotional vans and having a street team outside of the jail. He only served a few months since the case was dropped due to lack of evidence. But in the years that followed Gucci would constantly see his career hit bumps in the road as he damn near averaged one jail sentence a year until 2013 where he would get locked up for three years. The jail stints seemed to only add to his legend as he still managed to record music and release albums through the years though he was rarely around to promote them. Gucci just got out of jail again for the umpteenth time this past May and is hoping to cash in on his prison mystique for good this time. In just two weeks of freedom he has already recorded songs with Kanye West and Drake.

Verdict: HELPED. Gucci’s legend seems to grow each time he leaves and comes back. Plus, he is pretty much the A&R of Atlanta’s ever evolving rap scene. Everyone from Future to Young Thug owes at least a part of their success to Gucci, so he’s always going to have a way to work and get back on.

Prodigy

Mobb Deep’s best years were already behind them when Prodigy was sentenced to serve three-and-a-half years in prison on weapons charges in 2007. The group was fresh out of a failed tenure on 50 Cent’s G-Unit label and both of them were releasing music as solo artists. In the years that Prodigy was locked away the Hip Hop was veering farther and farther away from the 90s East Coast sound that he and his partner Havoc helped make popular. The good thing for P is that in those years the game became better suited for artists to release music independently. He has capitalized on that by releasing music at his own will since he got out in 2011.

Verdict: Hung Jury. Jail time took time away from P’s personal life obviously, but his career hasn’t really suffered or prospered because if it either.

Pimp C

Pimp C was already a legend in Southern Hip-Hop circles but he saw his name get bigger when he was in jail thanks to the massive “Free Pimp C” campaign that caught fire in 2002 and burned until he was finally released in December 2005. While he was locked away his recording home Rap-A-Lot tried to take advantage by releasing Sweet James Jones Stories in March 2005. Many of the songs were cast aways that were sitting in Pimp’s stash that probably weren’t going to see the light of day until Pimp was ready. But since he was a solo artist on Rap-A-Lot at the time, the label figured it would be a good idea to catch the “Free Pimp C” wave. The album did little to satisfy fans as most of the songs were obviously not the level of quality that UGK fans grew accustomed to. Pimp and Rap-A-Lot would make up for it by releasing Pimpalation in 2006 after he was out of jail. The album fared much better, selling over 500,000 copies earning Pimp a Gold plaque. The album served as a pre-cursor to UGK’s most successful album as a group, 2007’s Underground Kingz that featured the hit single “International Players Anthem.”

Verdict: HUNG JURY. The “Free Pimp C” campaign kept his name alive and set the stage for him to get out and succeed. But he only enjoyed the success temporarily as he died almost exactly two years after he was released. Jail took years out of the prime of Pimp C’s life as the Southern Hip-Hop genre he helped create was growing in popularity.

Z-Ro

Z-Ro spent years building his name in Houston for years releasing albums with small indie labels until he linked with Southern Hip-Hop powerhouse Rap-A-Lot Records in 2004. Unfortunately, when his debut album with the label, The Life Of Joesph W. McVey hit stores, he was in jail serving time on a drug possession charge. When he was released he put out another solid album with 2005’s Let The Truth Be Told. But, by the time his 2006 follow-up I’m Still Livin’ was released Z-Ro was in jail again. Since then Z-Ro has released an album or mixtape every year while still finding time to do cameo appearances on albums for artists ranging from E-40 to Nipsey Hussle to even Beyonce. He hasn’t had a radio or video impacting song since “I Hate U” in 2004. Had he been out to fully promote it, he may have been able to shake the underground underdog status attached to him.

Verdict: HURT. Z-Ro was unable to promote his most visible and successful albums due to being locked away.

Remy Ma

At this moment Remy Ma is near the top of the world with one of the biggest songs in rap right now, “All The Way Up” with Fat Joe. It’s similar territory for her as she is still widely recognized for appearing on the 2004 hit “Lean Back.” But in 2008 her career was completely derailed when she was convicted of assault, illegal weapon possession and attempted coercion in connection with a shooting incident that took place in 2007. Remy served six long years and was released in 2014. Unlike many of her contemporaries she didn’t record a gang of music before going in, so musically, she was pretty much silent. But, now that she is out she has already become the second most talked about woman on the mic outside of Nikki Minaj. She released a mixtape weeks after being released and “All The Way Up” is the song of the summer.

Verdict: HURT. Six years is a long time to be away from rap. She has a lot of catching up to do. 

Troy Ave

Troy Ave just joined this infamous club this week when he released his Free Troy Ave mixtape while awaiting trial on attempted murder charges. The Brooklyn-rapper released almost a dozen mixtapes and albums before getting some shine as an XXL Freshman in 2014. Though he popularity barely extended past his NYC stomping grounds he did fall in favor with bigger named artists like 50 Cent, T.I., Diddy and Rick Ross. Unfortunately now, his name is getting mainstream national recognition for his role in a deadly shooting that took place at a T.I. concert in May. In the intro to the mixtape Troy can be heard rapping about the details of the night that sent him to jail. It remains to be seen if his incarceration will be a stimulus or hinderance to his career success.

Verdict: TBA. Troy Ave will probably never achieve 2Pac’s popularity, but best believe if he is found not guilty, he will milk any and all comparisons to him. Just look at their similar wheelchair photos. Troy Ave’s next mixtape is already writing itself.