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Ol

50

Ol' Dirty Bastard

Crime: Fleeing drug rehabilitation and missing a court date
ODB has had numerous run-ins with the police, but it looks like his arrest in November 2000 ranks among one of the lightest. On Nov. 27, he was arrested at a fast food restaurant in Philadelphia for leaving a court-ordered drug rehabilitation center as well as missing his court hearing. During this time, he was in the midst of carrying out three years of probation.

Bobby Brown

49

Bobby Brown

Crime: Suspicion of driving under the influence
On Oct. 24, 2012, police pulled Bobby Brown over in Studio City, Calif., and smelled a "strong scent of alcohol." After performing a sobriety test, Brown was arrested and charged with suspicion of driving under the influence. He was released later that day. This was the second drunk driving charge he received that year.

Akon

48

Akon

Crime: Second-degree harassment and endangering the welfare of a minor
Remember catching that video of Akon tossing a 15-year-old off the stage during one of his gigs? Since the incident went viral, it wasn't too shocking when he was arrested and booked on charges of second-degree harassment and endangering the welfare of a minor. Despite heavy charges, Akon was only fined $350 plus received 65 hours of community service.

Funkmaster Flex

47

Funkmaster Flex

Crime: Three counts of criminal mischief and harrassment
On Feb. 4, 2011, police arrested DJ Funkmaster Flex in Westchester, N.Y., for allegedly assaulting his wife. An argument escalated, and Flex reportedly slapped a phone out of her hands when she tried to call the cops. By the time they arrived at the couple's home, Flex already fled the scene but was later found in his car. He was released on a on $500 bond.

Waka Flocka Flame

46

Waka Flocka Flame

Crime: Possession of marijuana and hydrocodone, possession of a firearm by a convicted felon and violation of probation for driving on a suspended license
Waka Flocka Flame turned himself in to Atlanta police on Jan. 3, 2011, after a previous police raid. He was arrested booked for possession of marijuana and hydrocodone, possession of a firearm by a convicted felon and violation of probation for driving on a suspended license. According to reports, he was held on $31,950 bail.

Gangsta Boo

45

Gangsta Boo

Crime: Conspiracy to commit the crime of armed robbery
Lola Mitchell, better known as Gangsta Boo, was arrested in December 2009, for her connection to the robbing of Dollar General store on July 28, 2009. She was initially booked with armed robbery, which is the same charge that the main suspect, Marcus Curtis received. There are no details on her exact role in the crime. However, after posting the $100,000 bond, she was reported to be facing the charge of conspiracy to commit the crime of armed robbery.

Lil Scrappy

44

Lil Scrappy

Crime: Probation violation
On Oct. 1, 2012, Lil Scrappy was arrested for failing to check in with his probation officer. The rapper's probation stems from a 2008 marijuana possession case. He pleaded with the courts to recall his arrest as he claimed that he was already placed on a non-reporting period for 18 months and was not aware of this particular reporting date.

Nate Dogg

43

Nate Dogg

Crime: Making terrorist threats, arson and domestic violence
In June 2000, Nate Dogg's Up in Smoke tour was interrupted when the rapper was arrested by a SWAT team in Ponoma, Calif. He apparently was taken into custody for kidnapping and assaulting his ex-girlfriend as well as torching his mother's car. He was eventually released from jail after posting a $1 million bail.

Young Buck

42

Young Buck

Crime: Gun possession
When police raided Young Buck's home in Sumner County, Tenn., on Aug. 3, 2010, they were only expecting to collect recording equipment, furniture and jewelry to settle his $300,000 tax debt. However, as they searched the rapper's home, cops found firearms, too. He was then arrested and charged with gun possession. He started his 18-month jail sentence in August 2012.

Max B

41

Max B

Crime: Multiple felony conspiracy murder charges
When Max B's ex-girlfriend told him that her new beau, Allan Plowden was spoiling her with expensive things, it pushed the rapper rob him, and, unfortunately someone was killed in the process. In 2006, with the help of his stepbrother, Max B went to a hotel room where Plowden was staying to rob him. David Taylor, Plowden's associate, was murdered during the incident. In June 2009, Max B and his stepbrother were found guilty on nine out of 11 charges placed on them.

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