Lil Wayne going to prison

On Tuesday, March 2, Lil Wayne was scheduled to begin serving a yearlong sentence for a gun charge. However, a bizarre fire in the basement at the New York Criminal Court where he was to be sentenced helped postpone the affair until March 8. Go figure.

Nevertheless, Weezy’s impending prison stint — barring any other freakish incidents — continues a sad trend of hip-hop’s biggest stars heading to prison at the apex of their careers. And like so many hip-hop tragedies, it’s become a cliché that easily lends itself to parody, even as many of the root causes — aggressive police tactics, America’s fascination with guns, et cetera — go unaddressed.

But let’s face it: most rap felons aren’t as noble as Chuck D.’s fictional draft dodger in “Black Steel in the Hour of Chaos.” So in commemoration of Lil Wayne’s entry into this not-so-exclusive club, here’s a look at 10 notable emcees whose misadventures landed them in the big house.  

1. Slick Rick
Back in the ’80s, rappers made songs about jail — remember the Original Fat Boys’ “Jailhouse Rap”? — but mostly stayed out of trouble. Leave it to Ricky “Slick Rick” Walters, of all people, to kick off the ’90s and the decade of “keeping it real.”

On his classic 1988 debut, The Great Adventures of Slick Rick, Slick Rick included comedic songs (“The Moment I Feared”) and satiric songs (“Children’s Story”) about the dangers of street life. But after the album went platinum, Slick Rick was drawn into a dispute by a cousin who initially worked as his bodyguard; when he fired his cousin, the man began harassing his family. On July 3, 1990, Slick Rick shot and maimed him on a downtown New York street.

Before he went to prison for attempted murder, Slick Rick went into the studio and recorded dozens of tracks that eventually became 1991’s The Ruler’s Back and 1994’s Behind Bars. The influential emcee indirectly started another trend: rap felons who use their final days of freedom cranking out hours of material for release while they’re in jail.

2. Tupac Shakur

Shakur’s year-and-a-half sentence for sexual-assault charges in 1994 may be the most famous legal case in hip-hop’s history. Hours before he was to receive his verdict in a Manhattan courtroom, mysterious assailants shot and robbed him at Quad Recording Studios; Puff Daddy and the Notorious B.I.G. happened to be on a separate floor. As the ambulance took him to Bellevue Hospital, he flipped a middle finger at the paparazzi that swarmed around him. The next day, jurors delivered a guilty verdict while Shakur sat in a wheelchair.

The case didn’t just yield the poignant Me Against the World, which Shakur finished before reporting to prison and which may be his best album. As he languished in jail pending appeal, Shakur fingered Puff Daddy and Biggie as conspirators behind the shooting in a Vibe magazine interview, officially kicking off the East Coast-West Coast conflict. Infamous rap imprint Death Row Records — which initiated its rivalry with Puffy’s Bad Boy Records during the 1995 Source Awards — posted a $1.4 million bond in exchange for a three-album contract with Shakur. The rest is infamy.

3. Dr. Dre

When Dre rapped “I’m expressing with my full capabilities/ Now I’m living in correctional facilities” on N.W.A.’s “Express Yourself,” he hadn’t actually served hard time. That changed in January 1994 when he led police on a high-speed chase through Beverly Hills and Westwood. The stunt violated his probation stemming from an earlier battery conviction, and resulted in a eight-month prison sentence. (Did he “get straight and meditate like a Buddhist”?)

Dre’s prison stint led him to clean up his life and, briefly, his music. Released in 1995, he left the label he cofounded, Death Row Records, after producing a final hit for newly signed artist Tupac Shakur, “California Love.” Launching Aftermath Entertainment, he recorded “Been There Done That.” Released in 1996, weeks before the murders of Shakur and the Notorious B.I.G., it was a prescient condemnation of the pointlessness of the gangsta lifestyle.

4. X-Raided

Though mostly known these days to “regional rap” collectors, Sacramento rapper and Crips gang member Anerae “X-Raided” Brown was a cause celebre when police arrested him for the 1992 home invasion and murder of a local activist. During his trial, the prosecutor used tracks from the teenager’s 1992 debut, Psycho Active, to argue that he was the trigger man in the gangland murder.

X-Raided was sentenced to 31 years in prison, but the bizarre case didn’t end there. He has continued to record music, starting with 1995’s Xorcist, which he rapped over a telephone as he sat in a holding cell. For subsequent albums, he relied on tape recorders smuggled into his jail cell. The lyrics are devoted to arguing his innocence — he admits he was at the scene of the crime but claims he didn’t pull the trigger — expressing regret over his former gang lifestyle, and describing the everyday horrors of life in prison.

5. Ghostface Killah

Remember when Dennis “Ghostface Killah” Coles rapped on “Verbal Intercourse,” “I don’t keep jack in my lap/ Don’t wanna see Tupac”? Ironically, the rapper was arrested in 1995 outside Manhattan nightclub the Palladium for attempted robbery. In 1998, he decided to serve six months on Rikers Island instead of taking the case to trial. The short stint interrupted the recording of his 2000 classic, Supreme Clientele. Ghost referenced his legal problems on the track “Saturday Nite.”

6. Chi-Ali

Making his debut in the video for De La Soul’s “Buddy,” Chi-Ali Griffith was the youngest member of the sprawling Native Tongues crew. In 1991, the teenage rapper released The Fabulous Chi-Ali, noted for the rap hit “Age Ain’t Nothing but a Number” (the title of which Aaliyah subsequently swiped for her debut album) and production by soon-to-be rap stars the Beatnuts.

The next time rap fans heard about Chi-Ali was on America’s Most Wanted; the true-crime show featured him twice for allegedly killing the brother of an ex-girlfriend in January 2000. He managed to evade capture for over a year before cops arrested him in March 2001. Currently serving 12 to 14 years in prison, Chi-Ali has become a favorite reference for rappers like Ludacris, who dropped a line about him in the 2003 hit “Stand Up.” “I’m young, wild, and strapped like Chi-Ali/ Blaow!”

7. C-Murder

Best known for the Dirty South hit “Down for My N*gg*z,” Corey “C-Murder” Miller benefited from big brother Percy “Master P” Miller’s No Limit empire and its brief chart reign during the late ’90s. But in 2002, C-Murder was charged with killing a teenager at a nightclub in Harvey, La.

Years of legal machinations followed. In 2003, C-Murder was convicted of second-degree murder, but months later, the presiding judge ordered a retrial. That decision was appealed to the Louisiana Supreme Court, which affirmed the judge’s decision in 2006. Last year, jurors convicted C-Murder again, and he was sentenced to life in prison. He continues to appeal and record albums like 2005’s The Truest S*** I Ever Said.

8. Prodigy

In 2008, Mobb Deep member Albert “Prodigy” Johnson began serving a three-and-a-half year sentence for gun possession. The time in prison ruined promotional plans for the thug rapper’s album H.N.I.C. Pt. 2. Undeterred, he has continued to give prison interviews, write open letters to his fans, and even wage “beefs” with rappers like Saigon and Joe Budden.

9. T.I.

Clifford “T.I.” Harris’ first major bid was what he referred to as “tying up loose ends.” In spring 2004, just as his breakthrough album, 2003’s excellent Trap Muzik, was taking off on the R&B charts, T.I. was locked up for violating probation on a 1997 conviction for selling cocaine. The Atlanta rapper only served a month of a yearlong sentence before earning a work-release program, but not before generating controversy by filming a promotional video inside the Cobb County prison where he was incarcerated.

The next time around, T.I. was ensnared by federal agents when he tried to buy guns with “no flash, no bang.” He was famously arrested hours before the 2007 BET Hip Hop Awards, which were scheduled to feature a performance by him; attendees learned about it during the ceremony.

Subsequent events — the guilty plea, the heartfelt apologia to his supporters (last year’s Paper Trail) — are well documented. To his credit, T.I. owned up his misstep, explaining that he stockpiled guns after surviving a 2008 murder attempt and the subsequent loss of his best friend. The incident propelled him to write the hit single “Dead and Gone.”

After serving eight months, T.I. was moved to a halfway house in December 2009, where he’ll finish his yearlong sentence in April.

10. Gucci Mane

Radric “Gucci Mane” Davis’ ascent is bookended by prison stints, an indicator of how a rapper’s rap sheet has become seemingly essential to his success. Shortly after the release of his 2005 debut, Trap House, he got into a dispute with former friend Young Jeezy over the Southern hit “Icy.” Reports differ: some claim Jeezy wasn’t properly compensated, while others allege Jeezy wanted to use the track for his major label debut, Let’s Get It: Thug Motivation 101, and was rebuffed by Gucci Mane.

Still unproven is whether Jeezy sent members of his Corporate Thugz camp to steal Gucci Mane’s chain. What’s undisputed, however, is that several men associated with the crew attacked Gucci Mane at his home in May 2005, and that Gucci Mane killed one of them in response. Arrested for murder, he claimed self-defense, and in January 2006 prosecutors decided not to press charges. (Gucci Mane and Young Jeezy squashed their beef last December.)

By then, Gucci Mane was serving six months for assaulting a nightclub owner in a separate incident in June 2005. Since his release in early 2006, he’s been back to prison twice for violating probation on the assault conviction, most recently in December 2009, even as the hip-hop industry has crowned Gucci Mane as one of the “hottest rappers in the game.”

Maybe it’s just a coincidence. Rhapsody Blog

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