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Over the years, hip-hop has witnessed a fair share of rappers get arrested or serve a bid. Some MCs have endured more notorious lock-ups with long drawn out trials, while others have been taken in for more minuscule stints. In most cases the photos from these trying periods never come to the surface but for a few, the mugshots are lingering on the internet as the ultimate time-capsules.

Tupac‘s mugshot from March 1995 is marveled over by rap heads. The slain hip-hop icon was photographed by the New York State Department of Correctional Services three months after he was convicted on felony sex abuse charges in December of 1994. Photos from Remy Ma‘s six-year prison stay have also popped up over time. Her husband Papoose is pictured visiting her at Bedford Hills Correctional Facility for Women. Lil Kim‘s infamous mugshot stems from a July 1996 arrest. The Queen Bee was booked on marijuana possession after cops raided the Notorious B.I.G.’s New Jersey home. Wiz Khalifa’s jail selfie is also unforgettable. The Pittsburgh rapper got caught up with authorities while on his way to the Neon Desert Music Festival in El Paso, Texas in May of 2014.

XXL compiled a list of the most memorable photos of rappers in Jail. Check it out above.