Following a stint at the Corcoran Substance Abuse Treatment Facility on drug charges, he joined the TV series Ally McBeal in 2000 and won a Golden Globe Award for the role.

[8] Downey moved often, mainly due to his father's film projects, living in places such as Woodstock, New York, London, New Mexico, California, Connecticut, and Greenwich Village.

[22][23] Downey began building upon his theater roles, making his debut on stage in 1983 at the Geva Theatre Center in Alms for the Middle Class for a three-week run.

"[28] That same year, Downey had a dramatic acting breakthrough when he played James Spader's sidekick in Tuff Turf and then a bully in John Hughes's Weird Science.

Molly Ringwald wanted him for the role of Duckie in John Hughes's 1986 film Pretty in Pink, but the part went to Jon Cryer.

[32][33] In 1987, Downey played Julian Wells, a drug-addicted rich boy whose life rapidly spirals out of his control, in the film version of the Bret Easton Ellis novel Less than Zero.

His performance, described by Janet Maslin in The New York Times as "desperately moving,"[34] was widely praised, though Downey has said that for him "the role was like the ghost of Christmas Future" since his drug habit resulted in his becoming an "exaggeration of the character" in real life.

[36][37] Zero drove Downey into films with bigger budgets and names, such as Chances Are (1989) with Cybill Shepherd and Ryan O'Neal, Air America (1990) with Mel Gibson, and Soapdish (1991) with Sally Field, Kevin Kline, Cathy Moriarty, and Whoopi Goldberg.

[42] In 1993, he appeared in the films Heart and Souls with Alfre Woodard and Kyra Sedgwick and Short Cuts with Matthew Modine and Julianne Moore, along with a documentary that he wrote about the 1992 presidential campaigns titled The Last Party (1993).

[46][47] He then subsequently appeared in Restoration (1995), Richard III (1995), Home for the Holidays (1995), Two Girls and a Guy (1997),[48] as Special Agent John Royce in U.S.

A month later, while on parole, he wandered into a neighbor's home through the unlocked front door while under the influence of a controlled substance and fell asleep in one of the beds.

[3] A week after his 2000 release, Downey joined the cast of the hit television series Ally McBeal, playing a new love interest.

[62][63] He also appeared as a writer and singer on Vonda Shepard's Ally McBeal: For Once in My Life album and sang with Sting a duet of "Every Breath You Take" in an episode of the series.

"[35] In January 2001, Downey was scheduled to play the role of Hamlet in a Los Angeles stage production directed by Mel Gibson.

[64] Before the end of his first season on Ally McBeal, Downey was arrested on Thanksgiving in 2000, when his room at Merv Griffin's Hotel and Givenchy Spa in Palm Springs, California, was searched by the police, who were responding to an anonymous 911 call.

[70] The Culver City arrest also cost him a role in the high-profile film America's Sweethearts,[69] and the subsequent incarceration prompted Gibson to cancel his Hamlet production.

"[73] In the same article, Dr. Manijeh Nikakhtar, a Los Angeles psychiatrist and co-author of Addiction or Self-Medication: The Truth, claimed she received a letter from Downey in 1999, during his time at Corcoran II, asking for advice on his condition.

'"[74] Downey flatly denied being "depressed or manic" and said that previous attempts to diagnose him with any kind of psychiatric or mood disorder have always been skewed because "the guy I was seeing didn't know I was smokin' crack in his bathroom.

"[74] After five years of substance abuse, arrests, rehabilitation, and relapse, Downey was ready to work toward a full recovery from drugs and return to his career.

In discussing his failed attempts to control his addictive behavior in the past, Downey told Oprah Winfrey in November 2004 that "when someone says, 'I really wonder if maybe I should go to rehab?'

[81] On November 23, 2004, Downey released his debut musical album, The Futurist, on Sony Classical, for which he designed the cover art and the track listing label on the CD with his son Indio.

The producers of the show accepted the offer and created the character of Patrick Pewterschmidt, Lois Griffin's long-lost, mentally disturbed brother, for Downey.

Lazarus undergoes a "controversial skin pigmentation procedure" in order to take on the role of African-American platoon sergeant Lincoln Osiris, which requires Downey to wear dark makeup and a wig.

[133] Downey next starred in a 2024 television adaptation of Viet Thanh Nguyen's historical satire novel The Sympathizer on HBO, portraying five supporting antagonistic roles representing the American establishment.

He released a CD in 2004 called The Futurist, and while promoting his film Tropic Thunder, he and his co-stars Ben Stiller and Jack Black were back-up singers for "The Pips" to Gladys Knight singing "Midnight Train to Georgia" for the season 7 finale of American Idol.

[165] When asked on The Oprah Winfrey Show how he was able to make his sobriety stick this time, Downey said, "It's really not that difficult to overcome these seemingly ghastly problems.

"[168] However, when asked about the quote in a 2015 interview to promote Avengers: Age of Ultron, he denied that his previous statement reflected any longstanding beliefs on his part and stated, "I wouldn't say that I'm a Republican or a liberal or a Democrat.

[171] In 2016, Downey appeared in an Internet video urging the American public to vote against Donald Trump in the then-upcoming presidential election.

[175] In January 2020, during the promotion of his film Dolittle, Downey announced that he had made the decision to adopt a vegan diet in response to the debate about the climate crisis, stating that "I'm a one-man carbon footprint nightmare colossus"[176] and believing he can do his part to contribute.

[180][181] In January 2024, Downey stated that he was a pescetarian and had to give up his vegan diet due to low levels of vitamin B12, calcium, and iron.