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Rappers With the Longest Rap Sheet

When it comes to hip-hop, there’s no shortage of rappers who have made headlines for more than just their music. While it's essential to remember that being a rapper doesn’t automatically mean someone has a criminal record, some high-profile artists have had past run-ins with the law. In fact, a few of the genre's biggest names have seen their reputations shaped (and some destroyed) by legal troubles.

For some artists, like Snoop Dogg, brushes with the law were part of a rough start in life, and they’ve managed to turn things around, now serving as role models and advocates for change. Others, however, seem to struggle with ongoing legal challenges, as shown by recent arrests involving P Diddy. We’ll dive into the rap world’s longest rap sheets, exploring both the notorious and the redemptive paths some of these artists have taken. From legendary names to more recent stars, we’ll look at the impact of these incidents on their lives and careers.

Snoop Dogg

Snoop Dogg

Would you believe that Snoop Dogg has been arrested for felony drug possession? We weren't surprised either. We were surprised that his eight total arrests included firearm possession and trespassing, as well as being picked up in connection to the death of a rival gang member (for which he was cleared of all charges).

Snoop Dogg has managed to turn his reputation around, though. While many fans still love him for his hard lifestyle, others can't help but watch him and Martha Stewart make gift baskets together on her TV show. Yeah, you read that right. Guess prison really changes a person. Some make music while others make wreaths. 

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T.I.

T.I.

T.I. began having trouble at the age of 14 when he was already arrested several times for dealing drugs. This continued through adulthood, with him being arrested just hours before he was to appear at the BET Hip Hop Awards. 

In total, T.I. has been arrested eight times, including two felonies. His rap sheet includes dealing and holding drugs, purchasing guns (one time from a federal agent), and attacking people. In 2010 alone, he was sentenced to 11 months in jail. 

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Lil Wayne

Lil Wayne

Lil Wayne has been arrested on drug charges many times. However, in 2007, he was arrested on gun charges in New York, leading to an eight-month prison sentence in Rikers Island in 2010.

Despite subsequent arrests related to drug and firearm possession, Lil Wayne’s career remained strong. Pardoned by former President Trump in 2021, he has since focused on music and business, moving past much of his criminal history.

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50 Cent

50 Cent

50 Cent, born Curtis Jackson, faced legal issues early on. He began dealing drugs in his teens and was arrested at 19 for selling to an undercover cop in 1994, resulting in a short stint in a boot camp-style prison program.

The rapper has also been arrested on weapons charges and alleged abuse. His final arrest came in 2016 for use of profanity in public in St. Kitts, a much tamer charge. 50 Cent has seemingly turned his life around and has been outspoken against Diddy.

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P Diddy

P Diddy

Sean "P Diddy" Combs’ first major arrest came in 1999 after a nightclub shooting in New York, but he was acquitted. In 2001, he was arrested for driving with a suspended license. Then, in 2015, Diddy was involved in an altercation at UCLA, where he was accused of attacking a football coach.

But now it looks like Diddy certainly did it this time, and the charges are more severe than ever.  Diddy has been charged with trafficking, abuse, and racketeering conspiracy. He was arrested on September 16, 2024.

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Tupac

Tupac

Tupac Shakur, a legendary rapper, had several high-profile legal issues during his career. In 1993, he faced charges after an altercation with film directors, and in 1994, he was convicted of SA receiving prison time.

Despite legal troubles, Tupac’s music continued to thrive, shaping his legacy as a voice for marginalized communities. His life ended tragically in a still-unsolved 1996 shooting, where his last words were insulting the police officer trying to save him.

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DMX

DMX

DMX has been in jail a total of 30 times on various offenses, including robbery, attacking, pretending to be a federal agent, carjacking, animal cruelty, failure to pay child support, reckless driving, driving under the influence, unlicensed driving, drug possession, probation violation, and tax evasion. 

It would be easier to list all of the crimes not on his rap sheet. Many of his arrests occurred before he got famous, but they didn't stop after he reached the top. In 2021, DMX passed away from a cocaine-induced heart attack.

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Kodak Black

Kodak Black

Kodak Black has been arrested multiple times for charges including robbery, attacking individuals, SA, kidnapping, false imprisonment, driving with a suspended license, violating house arrest, weapons charges, child endangerment and drug possession. He’s faced significant jail time since rising to fame in the mid-2010s.

Despite his repeated arrests, Kodak’s career has been resilient, with his music charting even during his incarcerations. In 2021, he was pardoned by former President Trump but has been arrested numerous times since for drugs and other charges.

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Chief Keef

Chief Keef

Chief Keef has a substantial rap sheet. He was arrested for manufacturing and delivering heroin at just 15. In a 2011 police chase (at 16), he aimed a loaded gun at officers and resisted arrest, which landed him in a juvenile detention center.

He has been arrested on different weapons charges, drug possession, parole violations, and for doing 110 mph in a 55-mph zone. His last arrests were in 2017 for allegedly attacking and robbing a producer (the charges were dropped) and for drug possession.

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Bobby Shmurda

Bobby Shmurda

Bobby Shmurda gained fame with a breakout song in 2014, but his career was interrupted when he was arrested that same year on conspiracy, drug, and weapon charges, receiving a seven-year prison sentence.

Since his release in 2021, Shmurda has focused on rebuilding his music career, with fans rallying behind his return. His arrest and incarceration have become part of his story, symbolizing both the challenges and resilience in the hip-hop industry.

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