In 1991, Douglas appeared with his father (in the senior Douglas's Emmy-nominated performance) in "Yellow", the Season 3 finale of the television series Tales from the Crypt. The father and son acting duo portrayed father and son characters with Eric a young officer in World War I brought up on charges of cowardice by his commanding general who is also his cold-hearted father.
Douglas was arrested multiple times throughout the 1990s. One of his first arrests came in 1991 for kicking a Beverly Hills police officer. On October 30, 1994, Douglas was arrested in Los Angeles for cocaine possession. Less than a month later, he was arrested for DUI and for leaving the scene of an accident when he crashed into a parked car while trying to leave The Comedy Store in West Hollywood after a fight. In May 1996, Douglas was arrested for possession of a controlled substance when police found eleven vials of crack cocaine and 1,085 Xanax pills in his Hell's Kitchen, Manhattan apartment. He pleaded guilty to the charges and was placed on probation and was ordered to complete a drug rehab program.