'Ally McBeal'

Despite his personal turmoil in the early 2000s, Downey continued working. He gave a memorable performance in Wonder Boys (2000) and had roles in several other films, including Auto Motives and Lethargy. Additionally, Downey made the move to the small screen in 2000, becoming a regular cast member of the popular show Ally McBeal, starring Calista Flockhart. With this new role, Downey once again reminded fans and critics of his talent, likeability and versatility. He went on to pick up a 2001 Golden Globe Award, and won a Screen Actor's Guild Award soon after.

But Downey's increasingly complicated personal life pressed his employer's patience. After that second arrest in April 2001, Downey's tenure on Ally McBeal came to and end; producers had decided to wrap production of the final episodes of the season without the actor. Around this same time, lawyers reached an agreement with prosecutors that required Downey to plead no contest to cocaine-related charges. He was sentenced to three years' probation—a ruling that allowed him to continue live-in drug treatment instead of returning to prison.