#34 Robert Downey Jr.
Years before finding massive success as Marvel Cinematic Universe’s Iron Man, Robert Downey Jr. was arrested multiple times. The actor was arrested in April 1996 for possession of heroin, cocaine, and an unloaded .357 Magnum handgun while he was speeding down Sunset Boulevard in Los Angeles. He later received three years of probation and was ordered to undergo compulsory drug testing. After missing a couple of court-ordered drug tests, he was sentenced to a three-year prison term.
Over the Thanksgiving 2000 holiday, just months after he was released in jail, Downey was arrested after his hotel room in Palm Springs was searched by the police, who were responding to an anonymous 911 call. Downey was under the influence of a controlled substance at the time of the arrest and in possession of cocaine and Valium. Downey pleaded no contest to the charges filed against him and was sent into drug rehabilitation and received three years of probation.