Al Pacino
Al Pacino played some big-time mobsters in movies, but it's very possible he was taking inspiration for those roles from his own life. In 1961, he was arrested in Rhode Island for possession of a concealed weapon. He and his friends were driving in a circle around the same block all wearing black face masks, so the police pulled them over. He spent three days in jail.
Justin Bieber
Justin Bieber had some troubling times as he grew up from a heartthrob singer to a rebellious teenager. He was arrested in 2014 for drag-racing, resisting arrest, and DUI. He pled guilty to resisting arrest without violence and to driving "without due care and attention." He's since grown up from his rebellious years and is happily married.