Rap On Trial: Hip Hop’s Most Notorious Criminal Cases

Hip Hop is seemingly never more than a whisker away from a criminal trial. Even as A$AP Rocky celebrates a not guilty verdict in his recent shooting trial, a number of rappers are currently at the center of open cases. None is more notable than Diddy, who will head to trial in May on charges of sex trafficking and racketeering, while Lil Durk, YNW Melly and Tay-K also face the prospect of serious prison time for their various alleged crimes.

Looking back over Hip Hop’s 52-year history, the long arm of the law has affected countless notable artists who have come to represent the genre. Some have been the victim of censorship and racism from ironfisted prosecutors looking to enact antiquated laws, while others — even with the luxuries of wealth, managers and security teams — find themselves drawn back to the allure of street life.

Out of these trials, Hip Hop has discovered a new hero: the criminal defense attorney. As A$AP Rocky’s attorney, Joe Tacopina, reaps the applause and does the Hip Hop media rounds, he is just the latest in a long line of high-profile and charismatic lawyers who have been employed by rappers to cast their magic over the courtroom.

Last year, Young Thug’s attorney Brian Steel became almost as famous as the rapper himself (to the point that Drake has even named a song after him), while JAY-Z’s legal right-hand Alex Spiro has been the rap icon’s shield in recent tumultuous times. They all stand in the shadow of Johnnie Cochran, however, who repped everyone from Diddy to O.J. Simpson and Michael Jackson.

With 2025 set to be another busy year in the courtroom, HipHopDX looks back at 10 of the most notorious trials in Hip Hop history.

2 Live Crew (1990)

The OG Hip Hop trial and one that had massive ramifications for the genre, as well as free speech itself. The infamous Miami rap group, who had developed a deserved reputation for sexually explicit lyrics, had angered critics so much that their third album, 1989’s As Nasty As They Wanna Be, was legally defined as “obscene” and banned from some retailers.

Days after the ruling, 2 Live Crew were arrested at a concert in Florida for performing songs from the album. The group were eventually acquitted, while a record store owner who was prosecuted for selling the album also had his conviction overturned.

“I went to jail for Hip-Hop so you could say the shit you’re saying on record don’t you forget it,” Uncle Luke reminded other rappers on social media last year.

2Pac (1995)

In the final years of his tragically young life, 2Pac could not move for controversy and legal battles. The most serious was when he and two other men were charged with sodomizing a woman in his hotel room in November 1993. The woman, Ayanna Jackson, claimed that she had consented to sexual activity with ‘Pac on previous occassions, but in this instance, the rapper as well as Haitian Jack, his tour manager Charles Fuller and an unidentified fourth man allegedly took turns raping her.

‘Pac would be acquitted of the sodomy charges but convicted for sexual abuse, though he always denied any wrongdoing. It is generally accepted that 2Pac was at least in the hotel room during the assault. His release from prison in 1995 — made possible by Suge Knight paying his $1.4 million bail — led to the rap war that would end his life.

Snoop Dogg (1996)

Before Snoop Dogg was the self-appointed uncle to the world, he was an alleged killer. In 1993, fresh off his star turn on Dr. Dre‘s The Chronic and just months before his own debut album Doggystyle would shake up the game, Snoop and his bodyguard McKinley Lee got involved in an altercation with a 20-year-old man named Philip Woldemariam, which resulted in the latter being shot to death. Both Snoop and Lee were charged with murder.

Tha Doggfather claimed self-defense and with a little help from famed defense attorney David Kenner, both he and Lee were eventually acquitted almost three years later. As the not guilty verdict was read aloud, a then-24-year-old Snoop held his head in his hands, making for one of the most iconic photos in Hip Hop history.

Suge Knight later claimed that the case cost him $6 million, including paying off someone in Snoop’s entourage who was attempting to blackmail the Death Row star.

JAY-Z (2001)

In the days before he was a billionaire, JAY-Z was a man of the streets and in the early days of his fame, it was a mentality that got him into deep water. In 1999, after Vol. 3… Life and Times of S. Carter had leaked ahead of its release, Hov and his crew confronted record executive Lance “Un” Rivera at a release party for Q-Tip‘s Amplified album. Rivera ending up getting stabbed. Jay subsequently turned himself in and pleaded not guilty to the attack.

Despite initially battling the case, the Roc-A-Fella rapper would eventually take a plea deal on the lesser charge of third-degree assault, which meant he only had to serve a probationary period. Rivera and Nas later claimed that Jay was not the assailant and sought to gain notoriety from the incident, while the Brooklyn-bred mogul copped to the incident in his autobiography Decoded.

Diddy & Shyne (2001)

Long before being charged with sex trafficking, Diddy was involved in one of the most high-profile trials of the early 21st Century that still causes debate to this day. Just days before the new millennium, the Bad Boy boss was out clubbing in New York with his then-girlfriend Jennifer Lopez and then-protégé Shyne. After a spilled drink, an argument escalated to guns being fired and three people were shot.

As Puffy and J-Lo attempted to leave the scene, police found a gun in their car, resulting in the former being charged with assault with a deadly weapon. Shyne would also be hit with an attempted murder charge over the shooting. While Diddy would be found not guilty, his Bad Boy signee was convicted of five different charges and was sentenced to a decade in prison.

In recent times, Shyne has claimed that a conspiracy was made against him to make him the fall guy, allowing Diddy to walk free.

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Mac Phipps (2001)

This was another case that posed a free speech threat to artists everywhere. Mac Phipps was a No Limit rapper on the rise in the late ’90s who got involved in a melee before a show that ended when a 19-year-old was shot and killed in the chaos. Phipps was convicted of manslaughter, despite another man saying he had discharged the gun and a witness later admitting they lied about the rapper being the shooter.

Prosecutors, when making their case against Phipps in court, used his lyrics to paint him as a violent man. They would read out his lyrics as evidence of the shooting, a controversial practice that prosecutors still attempt to implement to this day. Phipps was eventually released from prison in 2021 and has continued to maintain his innocence.

Gucci Mane (2005)

Gucci Mane and Jeezy’s feud is now the stuff of legend and occurred just as the two southern rap stars were exploding into the mainstream. Things came to a bloody crescendo when Pookie Loc, a friend of Jeezy’s, was shot and killed by Gucci in 2015.

While nobody denies that Guwop fired the fatal bullets, there was much debate over the events that led up to the killing. Gucci was charged with murder but claimed self-defence, saying that he was jumped by Pookie and a group of men at a house he was visiting. The rapper also managed to call on several eye witnesses who backed up his claims.

After sitting in jail for nine months, Gucci was eventually found not guilty as the case collapsed.

T.I. (2008)

Just as he was living up to his “King of the South” title and ready to unleash his sixth album Paper Trail, T.I. was brought back down to earth with lingering gun charges relating to an incident at the BET Hip Hop Awards in 2007. The charges were made worse by the fact that Tip was already a convicted felon.

Seeing the writing on the wall, he eventually agreed a plea deal with prosecutors that would see him spend a year behind bars and pay a $100,000 fine. The Grand Hustle general never quite managed to bounce back from the jail stint, which came at the worst time for his then-red-hot career, and he has never strayed too far away from controversy (or a lawyer) since.

6ix9ine (2018–2019)

Rewind back to 2018 and 6ix9ine is a controversial but popular presence in Hip Hop, particularly among younger fans, thanks to hits such as “Gummo” and “Fefe.” By the end of the year, the rapper had been involved in five different shooting incidents and arrested as part of a RICO case against the Nine Trey Gangsters shortly after departing a Breakfast Club interview.

Within three months of his arrest, the rainbow-haired rapper had turned into a government witness and revealed all about the inner workings of the Bloods-affiliated gang in what was a landmark moment for Hip Hop. No rapper as high-profile as 6ix9ine had ever cooperated with prosecutors before and certainly not as willingly or as comprehensively as he did.

The end result saw 6ix9ine receive a lenient two-year prison sentence, but any standing he had in Hip Hop had all but eroded. Six years later, he is better known for his subsequent legal problems, which range from sexual assault to domestic violence, than any attempts at recapturing his musical success.

Young Thug (2023–2024)

The longest trial in Georgia state history, Young Thug and YSL’s RICO case concluded last year with zero courtroom convictions, several plea deals and some of the most surreal moments in American trial history. While many of Thugger’s co-defendants (including Gunna) agreed plea deals before the case went to court, the Atlanta rapper — who was accused of being the leader of an alleged criminal street gang — fought his various charges head-on.

As the trial began to fall apart after the original judge was recused, the prosecution were criticized for their handling of witnesses and everybody involved grew weary of the entire ordeal, both sides went back to the negotiating table to hash out a plea deal over a dramatic Halloween night. While the agreement saw Thug immediately released from jail after two and a half years behind bars, he was also slapped with incredibly strict and lengthy probation conditions that has led to some wondering whether he should have put his faith in the jury.

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