The federal government has approximately a 90 percent conviction rate, meaning battling a fed case is more than likely and losing endeavor. Over the years, dozens of rappers have taken the FBI head-on with mixed results.

One of the earliest cases of the feds getting involved in hip-hop came in 1990, when a federal judge ruled that tracks off 2 Live Crew‘s 1989 As Nasty as They Wanna Be album, including “Me So Horny,” “D**k Almighty” and “The F**k Shop,” were too obscene, making it illegal in certain counties of the Sunshine State to play and sell the album. Group members were even arrested for violating a prohibition against obscenity when they performed the songs at a South Florida club. The landmark case went all the way to the Supreme Court, which acquitted the rappers, citing the freedom of speech.

YoungBoy Never Broke Again has battled the Bureau multiple times. In 2020, he was arrested at a music video shoot in Baton Rouge, La. and hit with federal gun charges. The following year, he was arrested by federal agents in California who were executing a search warrant in connection with the BR case. In 2022, YB took the Cali case to trial and was acquitted. In 2024, he was sentenced to almost two years in prison for the Louisiana gun charge.

Diddy is the latest rapper to face the feds. After being charged with racketeering conspiracy, sex trafficking and transportation to engage in prostitution in September of 2024, Puff was acquitted on RICO and sex trafficking charges during trial and is currently awaiting sentencing for prostitution related charges.

Read More: There Are Some Serious Hip-Hop Trials Going Down in 2025

Check out 21 times hip-hop took on the feds and the results below.

See a History of 20 High-Profile Hip-Hop Fed Cases