20 Celebrities Who Were Arrested at the Height of Their Fame

In April 2025, police arrested Haley Joel Osment at Mammoth Mountain ski resort for public intoxication and possession. After bodycam footage surfaced publicly, the actor resolved the case through a court-approved diversion program and community meetings.

Following a March 1976 concert in Rochester, police searched David Bowie's hotel room and detained him and musician Iggy Pop on marijuana charges. A grand jury declined to indict him, and Bowie's sharp, tailored booking photo became legendary in rock history.

At the summit of his global athletic fame, Mike Tyson was arrested in July 1991 in Indiana. A jury convicted him in 1992, and Tyson served three years in prison before returning to the ring to regain world championship belts.

In May 2007, a Los Angeles judge sentenced Paris Hilton to 45 days in jail for driving with a suspended license while on probation. Her incarceration became a massive global media spectacle before she was released after 23 days for good behavior.

In 1987, volatile young star Sean Penn was sentenced to 60 days in county jail after punching a movie extra on the set of Colors. Penn served 33 days before earning release. He went on to win two Academy Awards for Best Actor for Mystic River and Milk.

In November 1970, authorities stopped Jane Fonda at Cleveland Hopkins International Airport on suspicion of drug trafficking. The pills confiscated were standard vitamins, and all charges were dropped. Her raised-fist booking photograph became an enduring symbol of 1970s activism.

In July 2017, Savannah police arrested Shia LaBeouf following an aggressive confrontation with bystanders and officers on the street. Body camera video showed the actor shouting insults. LaBeouf pleaded guilty to obstruction, paid fines, and enrolled in court-mandated therapy programs.

In December 1999, New York police arrested Shawn Carter following a dispute at the Kit Kat Club where a music executive was stabbed. Jay-Z pleaded guilty to misdemeanor assault in 2001, receiving three years of probation while continuing his rise to billionaire music executive.

In September 2010, hotel security and police detained Bruno Mars inside a Las Vegas casino bathroom for possession of cocaine. Mars took accountability, completed 200 hours of community service, paid a fine, and kept his record clean before becoming a fifteen-time Grammy winner.

In April 2013, police stopped Reese Witherspoon and her husband in Atlanta on suspicion of driving while intoxicated. Witherspoon exited the vehicle and argued heatedly with the officer, resulting in her arrest. She promptly issued a public statement expressing deep remorse for her behavior.

In October 1999, Austin police responded to neighborhood noise complaints and found Matthew McConaughey playing bongo drums at home. Officers booked him on suspicion of drug possession, but prosecutors dismissed those charges. McConaughey paid a modest fine for violating local noise ordinances.

Following huge box-office hits like Mean Girls, Lindsay Lohan faced multiple arrests in 2007 for driving under the influence and substance possession. Her legal battles and probation hearings dominated international headlines for years before she staged a steady return to screen acting.

In January 2014, Miami Beach police pulled over nineteen-year-old Justin Bieber in a yellow sports car. Officers arrested him for driving under the influence and resisting arrest. Bieber avoided jail by agreeing to take anger management classes and making a charitable donation.

In December 2001, security officers stopped Winona Ryder for shoplifting thousands of dollars in designer garments. Her subsequent trial became a media circus. Ryder completed 480 hours of community service and three years of probation before returning to critical acclaim in Stranger Things.

In June 2003, federal authorities indicted Martha Stewart on charges stemming from her sale of ImClone stock. A jury convicted her of conspiracy and making false statements in 2004. Stewart served five months in federal prison camp before successfully rebuilding her corporate empire.

While on a major promotional tour for Four Weddings and a Funeral, Hugh Grant was arrested on Sunset Boulevard for lewd conduct in a parked vehicle. Grant defused the public relations fallout by offering a candid, contrite apology on late-night television that endeared him to audiences.

Between 1996 and 2001, Robert Downey Jr. faced multiple drug arrests, probation violations, and prison time that led to his firing from Ally McBeal. He achieved long-term sobriety in 2003 and rebuilt his career, becoming the cornerstone of the Marvel Cinematic Universe as Iron Man.

In June 2024, Sag Harbor police arrested Justin Timberlake after he ran a stop sign and failed field sobriety tests on Long Island. The incident occurred in the middle of his Forget Tomorrow world tour, prompting widespread media attention before he settled the case in court.

At the height of his international comedy and film career, Russell Brand faced serious criminal allegations in the United Kingdom. In November 2026, a Southwark Crown Court judge sentenced him to ten years and six months in prison following his conviction on sexual offenses.

Federal agents took Sean Combs into custody at a Manhattan hotel following a grand jury indictment. The billionaire music producer faced federal charges including racketeering and sex trafficking, marking a stunning legal reckoning for one of hip-hop's most powerful executives.