>In April 1996, Downey was arrested for possession of heroin, cocaine and an unloaded .357 Magnum handgun while he was speeding down Sunset Boulevard. A month later, while on parole, he trespassed into a neighbor's home while under the influence of a controlled substance and fell asleep in one of the beds.[34][35] He was sentenced to three years of probation and required to undergo compulsory drug testing. In 1997, he missed one of the court-ordered drug tests and had to spend six months in the Los Angeles County jail.[36]

>After Downey missed another required drug test in 1999, he was arrested once more. Despite Downey's lawyer, John Stewart Holden, assembling for his client's 1999 defense the same team of lawyers that successfully defended O.J. Simpson during his criminal trial for murder,[33] Downey was sentenced to a three-year prison term at the California Substance Abuse Treatment Facility and State Prison in Corcoran, California (a.k.a. "Corcoran II"). At the time of the 1999 arrest, all of Downey's film projects had wrapped and were close to release, with the exception of In Dreams, which he was allowed to complete filming. He had also been hired for voicing the devil on the NBC animated television series God, the Devil and Bob, but was fired when he failed to show up for rehearsals.[37][38]

>After spending nearly a year in California Substance Abuse Treatment Facility and State Prison in Corcoran, California, Downey, on condition of posting $5,000 bail, was unexpectedly freed when a judge ruled that his collective time in incarceration facilities (spawned from the initial 1996 arrests) had qualified him for early release.[8] A week after his 2000 release, Downey joined the cast of the hit television series Ally McBeal, playing the new love interest of Calista Flockhart's title character.[39] His performance was praised and the following year he was nominated for an Emmy Award in the Outstanding Supporting Actor in a Comedy Series category and won a Golden Globe for Best Supporting Actor in a mini-series or television film.[40][41] He also appeared as a writer and singer on Vonda Shepard's Ally McBeal: For Once in My Life album, and he sang with Sting a duet of "Every Breath You Take" in an episode of the series. Despite the apparent success, Downey claims that his performance on the series was overrated and said, "It was my lowest point in terms of addictions. At that stage, I didn't give a fuck whether I ever acted again."[17] In January 2001, Downey was scheduled to play the role of Hamlet in a Los Angeles stage production directed by Mel Gibson.