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Beanie Sigel

20

Beanie Sigel

Crime: Possession of a controlled substance and firearm-related charges
Beanie Sigel already has one prison sentence to deal with for pleading guilty to tax evasion. But before he was to start his jail time on Sept. 12, 2012, he was arrested for possession of codeine, prescription pills and a firearm on Aug. 29, less than a month before he was to due time. He's currently serving his sentence.

Buju Banton

19

Buju Banton

Crime: Drug trafficking and intent to distribute drugs
Buju Banton may be a legend in the reggae world, but unfortunately it doesn’t look like he’ll be basking in that glory anytime soon. Arrested in December 2009, he was accused of “conspiracy to possess with the intent to distribute cocaine, possession of a firearm in furtherance of a drug-trafficking offense and using a telephone to facilitate a drug-trafficking offense.” He was convicted of these charges in 2011, and is currently serving a 10-year prison sentence.

Trick Daddy

18

Trick Daddy

Crime: Possession of firearm, aggravated assault with firearm, possession of firearm by convicted felon
After threatening a man with a gun at a Miami basketball game on Feb. 3, 2003, Trick Daddy turned himself in to police and was arrested on three counts of assault and firearm charges. He has more than a few run-ins with the law, ranging from violating probation to trafficking cocaine.

Tupac Shakur

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Tupac Shakur

Crime: Sexual abuse
The late Tupac Shakur had his own string of bad decisions. This photo was taken after receiving his sentence for sexually abusing a 19-year-old fan from Brooklyn, N.Y., at the Le Parker Meridien Hotel in Manhattan. He was sentenced to one and a half to four and a half years jail time. He only served a few months and was granted an early release.

Vanilla Ice

16

Robert ‘Vanilla Ice’ Van Winkle

Crime: Domestic Battery
According to reports,Vanilla Ice had hit and kicked his wife but she later claimed that he only pushed her. He was found on his motorcycle two blocks from the couple's Palm Springs, Fla., home and said he only left so they both can cool down. He was arrested and booked at the Palm Beach County Jail. Ice claimed his wife is bipolar and an episode caused their dispute. This isn’t the first time he’s been booked. He was charged with domestic battery in 2004 in Broward County, Fla.

Young Jeezy

15

Young Jeezy

Crime: Two counts of carrying a concealed firearm without a permit
In March 2006, Young Jeezy, born Jay Jenkins, was arrested after an alleged shootout in Miami’s South Beach, which involved some members of his crew. Police stopped them in a vehicle after the incident and found a semi-automatic gun under his car seat and another gun near the armrest. He was cuffed and sent to Miami-Dade Country jail.

Soulja Boy

14

Soulja Boy

Crime: Possession of marijuana, possession of marijuana with intent to distribute and possession of a firearm during the commission of a crime
When Temple, Ga., police pulled Soulja Boy's SUV over on an equipment violation, they found marijuana, cash and guns in the vehicle. The rapper, his driver and three bodyguards were all arrested, charged with gun and drug felonies and booked at the Carroll County jail. Soulja Boy's bail was set at $10,000.

Khia

13

Khia

Crime: Multiple felonies and misdemeanors
While we know Khia for her telling men how she likes it between the sheets with 'My Neck, My Back,' she is also infamous for the number of times she’s been taken to jail by the cops. Between 1994 and 1999, Florida police have arrested her for a slew of different offenses ranging from carrying a concealed weapon to larceny and fraud. There’s even a collage floating around the interwebs chronicling her 20 mugshots in succession.

T.I.

12

T.I.

Crime: Illegal possession of machine guns
With drug possession and assault felonies under his belt, T.I. hasn't learned his lesson. On Oct. 13, 2007, federal agents arrested him after his bodyguard-turned-informant bought machine guns and silencers for him. While he was sentenced to 20 years in prison, a plea bargain that involved extensive community service reduced his sentence to a year that he started in May 2009.

Ja Rule

11

Ja Rule

Crime: Attempted criminal possession of a weapon and failure to pay federal income taxes
In July 2007, Ja Rule was pulled over in New York for speeding and was then arrested but not for driving too fast. He was taken in for drug possession and possession of a loaded semi-automatic handgun. He was released the next day after posting the $150,000 bail. In December 2010, he pleaded guilty for his 2007 arrest and started a two-year jail sentence in June 2011. After a month, 28 more months were added to his sentence for failing to file income taxes from 2004 to 2008. His release is reportedly scheduled for February 2013.

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