15 Dumb Things Rappers Have Done to Violate Probation

Chris Brown's fight with Frank Ocean could end up violating his probation. While it's a laughable cliché that the mainstream media often confuses R&B singers with rappers, they could be given a pass in the case of Chris Brown—much like a few troubled MCs, he's managed to violate his probation by making some pretty stupid mistakes.

Let's be real: The U.S. prison system is...not the best. It's systemically biased, particularly against minorities. Non-violent convictions have put huge numbers of reasonably harmless "felons" behind bars. Rape in jail has been normalized; society looks the other way or makes jokes about it. The conditions are unsanitary, and, in certain states, a life sentence is not-so-secretly a death sentence.

It's a messed-up situation, and the odds are stacked against young men from disadvantaged neighborhoods. But sometimes, people just do dumb stuff, and while prison remains hugely problematic for our culture, it's really hard to understand why certain people choose to make certain decisions, knowing probation looms over them.

In some cases it's costs rappers years of their lives. In others, it's obvious that addiction was a driving force behind their bad decision making—but bad decision making it remains.

Written by David Drake (@somanyshrimp)

RELATED: The 30 Biggest Criminal Trials in Rap History
RELATED: Chris Brown's 20 Douchiest Moments
RELATED: 25 Things Everyone Thinks About Hip-Hop (But Nobody Will Say)

Date: March 5, 1998

In 1996, Sacramento rapper C-Bo was sent to Soledad State Prison for two years for his role in a gang-related fight that occurred two years earlier. When released, the conditions of his probation required that he not be allowed to record music that promoted the "gang lifestyle" or was "anti-law enforcement."

C-Bo's 1998 release Til My Casket Drops, was, of course, full of gangbanging references, and so the rapper was put back in jail. The story attracted national attention, and he was ultimately freed, as the terms of his probation were clear First Amendment violations.

Date: January 2000

Shortly after ODB pleaded no contest to charges related to terrorist threats and possession of body armor, already a faintly ridiculous arrest, he violated the terms of his three-year probation. He had been sent to Impact, a drug rehab center in Pasadena, California, but was discharged soon after for getting drunk following a New York court appearance.

He was sent back to Impact while awaiting trial, but he fled a fugitive, performing at shows in New York before finally being captured by police after a crowd gathered around him at a McDonald's in south Philadelphia.

Date: January 2002

Rest in peace to the legend, of course, but still: Chad Butler sat behind bars for falling behind on his community service commitments, the result of a conviction for assault after he flashed a handgun at a woman at a Texas mall. He spent four years (!) in prison. With Pimp C behind bars, his UGK partner Bun B made "Free Pimp C," one of the most ever-present catchphrases in early-Aughts rap music.

Date: August 14, 2007

Foxy Brown was arrested in 2004 for her involvement in a fight in a nail salon. She allegedly violated her probation numerous times, first for skipping anger management classes, then for leaving New York without permission. Her final violation involved a conflict with her neighbor. When the rapper was confronted for playing loud music, she allegedly smacked her neighbor with a cell phone. Reach out and touch someone?

Date: October 29, 2007

Ras Kass has been arrested for numerous DUI charges throughout his career. He was on probation when, in 2007, he flew out to Atlanta to attend BET's annual award show. His probation officers weren't too happy when he was spotted in the BET freestyle cyphers that year, rapping alongside Joell Ortiz and Cassidy, and he spent the next two years in jail.

Date: January 2008

Beanie Sigel was arrested for violating probation related to a gun conviction in 2008. He was subsequently sentenced to serve one year and one day in prison and six months in a halfway house. His probation had already been extended, after it had been discovered that he was continuing to associate with Terrence Butler, who the court considered a "known felon."

On January 9, 2008, the Judge found out that Sigel had traveled to Atlantic City's Tropicana Casino & Resort without permission, after a gossip item in the newspaper revealed that he was spending significant amounts of money at a craps table. He rolled snake eyes with the judge, though.

Date: November 2009

Lil Boosie was facing as many as 20 years with a five-year mandatory minimum for marijuana and gun charges in 2008. He took a plea deal for two years instead, which likely would have kept his time inside to around a year. While awaiting sentencing, though, he was put on electronic monitoring. When the judge found out Boosie's ankle bracelet registered numerous violations, his jail time was doubled.

Date: March 17, 2010

Waka Flock was arrested for possession of a sawed-off shotgun back in 2006. He was still on probation stemming from that offense when it was discovered that he'd left Georgia without permission in 2010. He was arrested and taken into custody in Houston.

Date: September 1, 2010

Pretty sure there was an episode of Saved By the Bell about this. In 2010, a judge sent T.I. back to prison for 11 months after he violated probation during a traffic stop, when police smelled marijuana.

He was on probation because of an attempt, three years earlier, to buy three illegal machine guns in a grocery store parking lot. The conditions of his probation required that he stress to teens the importance of staying off of drugs and out of trouble, so a drug arrest was understandably frowned upon by the judge.

Date: November 2, 2010

In November of 2010, police caught Gucci Mane driving on the wrong side of the road; they pulled him over and had to subdue him with pepper spray. The charges were dropped, but ultimately still counted as a violation of his probation.

The following month, in an effort to remain a free man, he filed a "special plea of mental incompetency," and in January 2011, a judge ordered him to undergo mental competency tests at Anchor Hospital, where he was admitted on January 4.

This wasn't his only probation violation. In April 2011, he was arrested on misdemeanor battery charges after pushing a woman out of a moving vehicle. Earlier in his career, he violated probation by failing to complete required community service hours and by testing positive for drugs.

Date: November 18, 2010

DMX had lengthy rap sheet in the state of Arizona already, including charges for animal cruelty, weapons possession, and reckless driving. But it was his drug infractions that brought him the most trouble with probation officers, who sent him back to jail in March 2010 for admitting to using cocaine. In November, he again violated the terms of his probation. He was caught with Oxycontin and arrested for avoiding drug tests and counseling, as well as unrelated driving infractions.

Date: May 14, 2012

Mystikal is one of hip-hop's most talented artists, but his 2004 conviction for sexual battery and extortion was a hard pill to swallow for even his die-hard fans. He emerged from prison in 2010, and went right back into making music, even receiving a record contract from Cash Money. Then, in February 2012, he was arrested again, this time for domestic abuse battery, a misdemeanor. He received a three-month sentence, which doesn't seem likely to rehabilitate him, if a six-year prison stint couldn't.

Date: July 2, 2012

When the Pitchfork.TV branch of Pitchfork Media wanted to interview then-16-year-old rapper Chief Keef, the star of the viral video "Bang" seemed like a natural fit for a gun range. Hey, who wouldn't want to show the kid responsible gun ownership? As it turned out, the answer was Illinois prosecutors, who decided that the promotional video violated the terms of his probation.

Keef wasn't allowed to go near a gun, and the video by Pitchfork obviously captured him handling one. When prosecutors sought the original tape, Pitchfork tried to appeal, arguing that it should be protected under First Amendment privileges, but a judge wasn't convinced. The prosecution successfully obtained the tape, and Keef was sentenced to two months in the Illinois Youth Center in St. Charles, Illinois.

Date: October 1, 2012

In 2008, Scrappy was convicted for possession of marijuana, carrying a concealed weapon, obstruction of officers, and fighting. He received five years of probation, and made it into year four when he was arrested in October 2012 for failing to report regularly to his probation officer. So close, so far.

Date: December 18, 2012

In 2008, Meek Mill was convicted for gun and drug charges and spent eight months behind bars. He remained on probation, until December of 2012 when a judge found that a missed meeting with his probation officer and hadn't followed the restricted tour schedule required by the court. Meek was forced to cancel his tour (and worst of all, an appearance on the Conan O'Brien show).