Black Hawk Down actor Tom Sizemore was ordered into drug treatment rather than prison after pleading guilty in October 2004 to possession of methamphetamine. But a host of other problems plagued his recovery, including probation for a 2003 conviction for abusing his former girlfriend, "Hollywood Madam" Heidi Fleiss. He was found in violation of probation on drug charges for falsifying urine tests. A judge sentenced Sizemore to three years probation after the actor tearfully admitted he had used methamphetamine in January 2006.

On May 2007, Sizemore was arrested again for possession of methamphetamine, this time in Bakersfield, Calif. In June, Sizemore was sentenced to 16 months in jail for violating his parole, which was reduced to less than half that when the time he had served in various rehab programs was credited along with his good behavior. He avoided jail time in the Bakersfield case by pleading to a lesser charge, gaining him yet more probation time. In May 2009, Sizemore was arrested again, this time for violation of his Bakersfield probation. He was released, though, and the next day began filming the third season of Celebrity Rehab, sharing camera-time with none other than ex-girlfriend Fleiss. Both survived the season, going on to try their luck on Sober House.

Sizemore was arrested yet again on September 20, 2011, this time on an outstanding warrant for misdemeanor battery. He posted $26,000 bail and was released.