While often heralded as one of the greatest musicians of all time, rock icon David Bowie once very briefly held another superlative: The most wanted man in Rochester, New York. Shortly after performing at the Community War Memorial in March 1976, Bowie and two others, including a young Iggy Pop, were arrested at Americana Rochester Hotel for allegedly possessing a half pound of marijuana. While the group was arrested and booked, a grand jury ultimately decided to let their boy go — a good decision considering the artist and his crew were facing 15 years behind bars. The singer ended up putting his freedom to good use, going on to release several revered albums, including “Heroes.” He died in January 2016.

While Bruno Mars may be allegedly staring down $50 million of gambling debt accrued during his Las Vegas residency, this isn’t the first time the singer has found himself in trouble in Sin City. In 2010, he was arrested after being caught with C—ne in the bathroom of the Hard Rock casino. "I was young, man! I was in f****** Vegas. I wasn't thinking,” he told GQ of the incident roughly three years later. "I was given a No. 1 record and I'm out doing dumb s--t."

Long before the star coined “sliving” she found herself serving … time behind bars. Paris Hilton’s legal woes all began in 2006 after the socialite was pulled over for erratic driving. After being pulled over, her blood alcohol content was revealed to be over the legal limit. While initially sentenced to 36 months of probation and slapped with a fine, Hilton landed prison time after she was caught driving with a suspended license. Although initially sentenced to 45 days in the slammer, she was released after three weeks. Roughly three years later in 2010, the heiress was arrested for possession of c—ne, winding up with 200 hours of community service and a fine. Since then, the DJ has managed to stay out of trouble. After all, to paraphrase her catchphrase, staying out of jail is very hot.

Paris Hilton wasn’t the only 2000s celebutant who found themselves at odds with the legal system. In 2007, the Photoshop icon was arrested for driving under the influence. Much like her sister’s former boss, Kardashian ultimately violated her probation — she missed several of her court-mandated community service sessions — and wound up facing jail time. While she reported to a jail in Lynwood, California — an act that not only appeared on Keeping Up with the Kardashians but gave us the ever-iconic line of “Kim, would you stop taking pictures of yourself? Your sister's going to jail." — Kardashian was released after just three hours due to overcrowding. Even so, the star has still expressed remorse for her actions. "I went to jail when I was like 22. I went to jail for a DUI, not smart,” she said during a 2022 episode of The Kardashians. “Don't drink and drive."

Long before shooting to stardom as one of the greatest modern female rappers of all time, Nicki Minaj found herself in some hot water. Back in 2003, a young Minaj was arrested in New York City for criminal possession of a weapon. While not much is known about the details of her stint with the law, she’s clearly turned a corner… although her fans haven't.

Despite her reputation as America’s Southern sweetheart … and every middle-aged white woman’s favorite actress, Reese Witherspoon is no stranger to the law. Back in 2013, the actress and her then-husband, Jim Toth, were pulled over while driving in Atlanta, Georgia. The star, who later admitted she was also under the influence at the time of her spouse’s arrest, was arrested for disorderly conduct after refusing to stay in their vehicle as her S.O. completed field sobriety tests. "I clearly had one drink too many and I am deeply embarrassed about the things I said,” Witherspoon shared in a statement a few days after the arrest, seemingly referencing her comments questioning whether the officer was “ about to find out” who she was. “It was definitely a scary situation and I was frightened for my husband, but that is no excuse,” she continued. “I was disrespectful to the officer who was just doing his job. I have nothing but respect for the police and I'm very sorry for my behaviour."

Long before spearheading the first Marvel Cinematic Universe as Tony Stark, Robert Downey Jr. famously struggled with drug addiction. Between 1996 and 2001, the actor was arrested several times on drug-related charges, gun possession charges and more. The star ultimately spent four months in the Los Angeles County Jail. Yet following his final arrest in April 2001, the star decided to tackle his addiction once and for all. "I said, 'You know what? I don't think I can continue doing this,’” he told Oprah of his decision to seek professional guidance. “I reached out for help, and I ran with it. You can reach out for help in kind of a half-a—ed way and you'll get it and you won't take advantage of it. It's not that difficult to overcome these seemingly ghastly problems ... what's hard is to decide to do it." Downey has remained sober since 2003, a feat that helped him make his mark in the Marvel Cinematic Universe and more recently, nab the Academy Award for Best Supporting Actor for his role in Oppenheimer.