Hip-Hop is a culture that lives and thrives in the inner-cities of the United States. The harsh brutalities of these areas are reflected in the gangster themes of so many rap artists. Many of these rappers are talking about the reality they lived, and for some of them, they continue to go back to the illegal activities and patterns they tried so hard to escape. Below is a list of 6 rappers who are constantly in legal trouble and keep on going in and out of jail.
Philadelphia rapper Beanie Sigel was scouted by Jay-Z and Damon Dash when their successful record label was ruling Hip-Hop. In the early 2000s, Beanie was one of the few rappers who could seriously hold his own and match the lyrical prowess of Jay-Z on a track. But through the years, Sigel kept on getting into trouble and spending several stints in jail. He’s been charged for federal possession of arms, attempted murder, drug possession, and even now, he’s currently doing time for tax evasion. It’s especially sad when someone so talented can’t seem to get his life together.
Atlanta Rapper Gucci Mane has been in jail so much, that by now, he probably has his own dedicated wing at the county lock-up. Ever since he became active in the Hip-Hop industry in 2005, almost all the news you hear about him revolves around new legal trouble he’s gotten into. His rap sheet goes on forever: cocaine charges, battery charges, murder charges, probation violations, aggravated assault, hitting a fan in the head with a bottle and even driving on the wrong side of a road. He’s always in and out of jail and he was even once remanded to a psychiatric hospital. The one thing that keeps him relevant is the copious output of music that he manages to put out on a very regular basis. He is currently in jail till 2016 for being a convicted felon in possession of an illegal firearm.
Freck Billionaire is a rapper that could have really made a huge splash on the scene if he was just able to keep himself out of trouble and on a clean and productive path. Between the ages of 18 and 22, it’s been reported that Freck was arrested 19 times. For a small stretch, it looked like things were really turning around for the Philly rapper. He was rolling with Brooklyn rapper Fabolous and making songs with established artists like Foxy Brown and Omarion. He was arrested again in 2008 for selling crack to an undercover police officer and was sentenced to another 19 months in jail. At one point, he was even supposed to sign with Floyd Mayweather’s label, but with all his legal issues, even that opportunity quickly dissolved.
27-yr-old rapper Meek Mill is one of the biggest success stories in Hip-Hop within the last five years. The Philly rapper emerged on the scene with his rapid rhyming style and the contagious energy he delivers on his songs. He was signed to T.I. shortly, but he eventually made his home with Rick Ross’s MMG label. His debut album Dreams & Nightmares was a huge success, but sadly, he is one of those rappers that can’t seem to leave the street life alone. In 2008, he was sentenced to 11-23 months in jail for drug dealing and gun possession. He was released a year later under a 5-year probation deal. In May 2013, he violated his probation for travel violations and social media postings that were deemed as threats to his judge. In July of 2014, his probation was revoked again and he was sentenced to 3-6 months in jail – a sentence he’s currently serving.
Earl “DMX” Simmons has had one of the most successful careers ever in Hip-Hop, but he’s also one of the most troubled rappers. His very early years were extremely rough, and he has so many inner demons that he is still haunted by. At the current age of 43, he is the father of 12 kids and he has had countless run-ins with the law from the late 90’s till today. His numerous stints in jail have been for a plethora of offenses: driving without a license, cocaine possession, parole violation, weapons possession, speeding and even animal cruelty. He’s been in the studio recently working on new music with Swizz Beatz. Maybe he can finally put all his issues behind him and concentrate on making the amazing Hip-Hop we know he is capable of.
It seems like the curse that affects young Hollywood entertainers also applies to the world of Hip-Hop. Child rapper Shyheim was affiliated with the Wu-Tang in the late 90s, but as the years went by, his transition to adult rapper didn’t proceed so smoothly. He served more than a year in prison in 2002 for a second-degree attempted robbery conviction. In April 2013, he caught another case for a raid on his apartment which yielded a stash of drugs and guns. He was out on $10,000 bail when he was involved in a fatal hit-and-run case on New Year’s Day this year. He left the scene but later turned himself into the authorities. He made a plea agreement this summer and the deal resulted in a five to 15 year prison stay. Shyheim is currently in jail serving this latest sentence.