During 1996-2001, Downey was arrested several times on drug-related charges, going through drug treatment programs unsuccessfully. It was between these stays in prison that Downey joined the cast of the hit television series Ally McBeal, playing the new love interest of Calista Flockhart's title character. His performance was praised and 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 TV Film, but his character was written off when Downey was once again arrested in 2000. After Ally McBeal, and one last stay in a drug treatment program, Downey's career began to take off again, receiving semi-independent films like The Singing Detective (2003), A Scanner Darkly (2005) and Kiss Kiss Bang Bang (2005). He also had supporting roles in the mainstream films Gothika (2003) and Zodiac (2007). In 2004, Downey released his debut studio album The Futurist.
In 2006, Downey was cast as the title character in the comic book adaptation Iron Man which premiered in the summer of 2008, making almost $100 million at the domestic box office in its opening weekend and receiving rave reviews which cite Downey's performance as a highlight of the film. He also has a cameo in The Incredible Hulk as Tony Stark, Iron Man's alter ego. His other 2008 films include The Soloist, Charlie Bartlett, and the Ben Stiller-directed Tropic Thunder.
During his childhood, Downey had minor roles in his father's films, making his debut at age 5 as a sick puppy in the absurdist comedy Pound (1970), and then at age 7 he was murdered by God in the surrealist Greaser's Palace (1972). He grew up in Greenwich Village and attended the Stagedoor Manor Performing Arts Training Center in upstate New York, as a teenager. When his parents divorced in 1978, Downey moved to California with his father, but in 1982 he dropped out of Santa Monica High School and moved back to New York to pursue an acting career full time.
At the age of twenty, he joined the cast of the weekly television comedy show Saturday Night Live (SNL), but was a cast member for only one season. After leaving SNL during the last half of the eighties, Downey had his breakthrough when in 1985 he played James Spader's sidekick in Tuff Turf and then a bully in John Hughes's Weird Science. He was afterwards considered for the role of Duckie in John Hughes's film Pretty in Pink (1986), but his first lead role would be with Molly Ringwald in The Pick-up Artist (1987). Because of these and other coming of age films Downey did during the 1980s he is sometimes named as a member of the Brat Pack. Also during 1987 he appeared in Less Than Zero, where his portrayal of a drug-addicted rich boy was described by The New York Times as "desperately moving". Downey has said that for him "the role was like the ghost of Christmas Future", since his drug habit resulted in him becoming an "exaggeration of the character" in real life. Zero drove Downey into films with bigger budgets and names, such as Air America (1990) with Mel Gibson, and Soapdish (1991) with Sally Field, Kevin Kline and Whoopi Goldberg.
In 1992, he starred as Charlie Chaplin in Chaplin, a role for which he prepared extensively, learning how to play the violin and tennis. He even had a personal coach in order to imitate Chaplin's posture and way of carrying himself. The role garnered Downey an Academy Award nomination for Best Actor at the Academy Awards 65th ceremony, losing to Al Pacino in Scent of a Woman. His other films in the 1990s included Heart and Souls, Only You, Natural Born Killers, Restoration, and The Last Party, which is a documentary written by Downey.
In April 1996, Downey was arrested for possession of heroin, cocaine and an unloaded .357-caliber Magnum handgun, while he was speeding down Sunset Boulevard. A month later, when on parole, he trespassed into a neighbor's home while under the influence of a controlled substance, falling asleep in one of the beds. He was sentenced to three years of probation and required to undergo mandatory drug testing. In 1997 he missed one of the court-ordered drug tests and had to spend four months in the Los Angeles County jail. The same happened in 1999, only this time he was sentenced to a three-year prison term. After spending nearly a year in a state prison in Corcoran, California he was released on $5,000 bail. For his 1999 defense, Downey's lawyer, Peter Knecht, assembled the same team of lawyers that successfully defended O. J. Simpson during his criminal trial for murder. At the time of the 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.
A week after being released in 2000, Downey joined the cast of the hit television series Ally McBeal, playing the new love interest of Calista Flockhart's title character. 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 TV Film. 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". Despite the apparent success, Downey claims that his performance on the series was overrated and that "It was my lowest point in terms of addictions. At that stage, I didn't give a fuck whether I ever acted again." In January 2001, Downey was scheduled to play the role of Hamlet in a Los Angeles stage production directed by Mel Gibson.
Before the end of his first season on Ally McBeal, Downey was arrested during Thanksgiving 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. Downey was under the influence of a controlled substance and in possession of cocaine and Valium. Despite the fact that if convicted he could face a prison sentence of up to four years and eight months, he signed on to appear in at least eight more Ally McBeal episodes. In April 2001, while he was on parole, a Los Angeles police officer found him wandering barefoot in Culver City, near southwest Los Angeles. He was arrested for suspicion of being under the influence of drugs but was released a few hours later, even though tests showed he had cocaine in his system. After this last arrest producer David E. Kelley and other Ally McBeal executives ordered last-minute re-writes and re-shoots, and dismissed Downey from the show, though Downey's character had resuscitated Ally McBeal's ratings. The Culver City arrest also cost him a role in the high-profile film America's Sweethearts. In July 2001, he pleaded no contest to the Palm Springs charges, avoiding jail time. He was instead sent into drug rehabilitation and put on a three-year probation, benefiting from the California Proposition 36, which had been passed the year before and aims to help non-violent drug offenders overcome their addictions instead of sending them to jail.
The book Conversations With Woody Allen reports that director Woody Allen wanted to cast Downey and Winona Ryder in his film Melinda and Melinda in 2000, but was unable to do so because he could not get insurance on them, stating, "We couldn't get bonded. The completion bonding companies would not bond the picture unless we could insure them. We were heartbroken because I had worked with Winona before [on Celebrity] and thought she was perfect for this and wanted to work with her again. And I had always wanted to work with Bob Downey and always thought he was a huge talent."
Downey's first acting job after being ordered into a drug treatment program in July 2001 was a month later, when Sam Taylor-Wood suggested to Elton John the idea of having an actor lip-syncing to the song in the video for the single "I Want Love". John thought Downey would be perfect, and the video ended up being a one-shot video centered on Downey. Downey was able to return to the big screen only after Mel Gibson, who had been a close friend to Downey since both had co-starred in Air America, paid Downey's insurance bond for the 2004 film The Singing Detective. On November 23, 2004, Downey released his debut musical album, The Futurist, on Sony Classical, for which he designed the cover art. The album received mixed reviews, but Downey stated in 2006 that he probably won't do another album as he felt that the energy he put on doing the album was not compensated. Also in 2004, Downey was named "Man of the Year" by Harvard's Hasty Pudding Theatricals. He returned to mainstream films in the mid 2000s with Gothika, for which Joel Silver withheld 40 percent of his salary until after production wrapped as insurance against his addictive behavior; similar clauses have become standard in his contracts since then. After Gothika Downey appeared to have become a more reliable actor and was cast in a number of leading and supporting roles, including the well received semi-independent films Kiss Kiss Bang Bang, A Guide to Recognizing Your Saints, Good Night, and Good Luck. and A Scanner Darkly, Disney's poorly received The Shaggy Dog, the mainstream Zodiac and Steven Shainberg's fictional biopic of Diane Arbus, Fur, where Downey's character represented the two biggest influences on Arbus's professional life, Lisette Model and Marvin Israel.
Also in 2006, Downey guest starred on Family Guy voicing in the episode "The Fat Guy Strangler, which originated when Downey telephoned the show production staff and asked if he could produce or assist in an episode creation, as his son is a fan of the show. The producers of the show accepted and created the character of Patrick Pewterschmidt, Lois Griffin's long lost, mentally disturbed brother, for Downey. It was during this time that Downey signed on with publishers HarperCollins to write a memoir, which in 2006 was already being billed as a "candid look at the highs and lows of his life and career". In 2008 Downey returned his advance to the publishers and cancelled the book without further comment.
In 2006, Downey was surprisingly cast for the title character in the film Iron Man, with director Jon Favreau explaining the choice by stating: "Downey, Jr., wasn't the most obvious choice but he understood what makes the character tick. He found a lot of his own life experience in 'Tony Stark.' Favreau insisted in having Downey as he repeatedly claimed that Downey would be to Iron Man what Johnny Depp is to the Pirates of the Caribbean trilogy, a lead actor that could both elevate the quality of the film and increase the public's interest on it. For the role Downey had to gain more than 20 pounds of muscle in five months so as to look like he "had the power to forge iron. The film was globally released between April 30 and May 3, 2008, grossing over $300 million in the United States and Canada and receiving rave reviews which cite Downey's performance as a highlight of the film. As a result, both Downey and Favreau have already stated their interest in making Iron Man a trilogy. He also made a small appearance as Iron Man's alter ego Tony Stark in the film The Incredible Hulk and is in talks to appear as Iron Man in the future film of the Avengers, all of which are a part of Marvel Studios' attempt to depict the same Marvel Universe on film.
After Iron Man, Downey appeared in another 2008 summer film, the Ben Stiller directed Tropic Thunder, starring Stiller and Jack Black. For the role Downey had to wear blackface makeup, something that Stiller and Downey feared could become controversial:
When asked by Harry Smith on CBS's The Early Show who his model was for his portrayal of the self-absorbed method actor Kirk Lazarus in Tropic Thunder, Downey laughed before responding, "Sadly, my sorry-ass self.
The first role Downey has accepted since Iron Man is the lead in Guy Ritchie's Sherlock Holmes. He is also in negotiations to star in DreamWorks Pictures' adaptation of the graphic novel Cowboys & Aliens, a potential 2010 tentpole that plans to mix the genres Western and science fiction.
Downey says he has been drug-free since July 2003, thanks to the help of his family, therapy, meditation, twelve-step recovery programs, yoga and the practice of Wing Chun Kung Fu. He has described his religious beliefs as "Jewish-Buddhist," although he has been interested in the past by Christianity and the Hare Krishna ideology.
|1970||Pound||a puppy||Directed by Robert Downey Sr.|
|1972||Greaser's Palace||uncredited||Directed by Robert Downey Sr.|
|1975||Moment to Moment||uncredited||Directed by Robert Downey Sr.|
|1980||Up the Academy||Caleb Yoon||Directed by Robert Downey Sr.|
|1983||Baby It's You||Stewart|
|1985||Deadwait (short subject)|
|Tuff Turf||Jimmy Parker|
|1986||Back to School||Derek|
|1987||The Pick-up Artist||Jack Jericho|
|Less Than Zero||Julian Wells|
|1988||Johnny Be Good||Leo Wiggins|
|Rented Lips||Wolf Dangler|
|1989||That's Adequate||Albert Einstein|
|True Believer||Roger Baron|
|Chances Are||Alex Finch|
|1990||Air America||Billy Covington|
|1991||Too Much Sun||Reed Richmond|
|Soapdish||David Seton Barnes|
|1992||Chaplin||Charlie Chaplin||Academy Award for Best Actor nomination|
|1993||Luck, Trust & Ketchup: Robert Altman in Carver Country||documentary|
|Heart and Souls||Thomas Reilly|
|The Last Party||himself||documentary written by Downey|
|Short Cuts||Bill Bush|
|A Century of Cinema||documentary|
|Natural Born Killers||Wayne Gale|
|Only You||Peter Wright, alias Damon|
|1995||Richard III||Lord Rivers|
|Home for the Holidays||Tommy Larson|
|Mr. Willowby's Christmas Tree (TV)||Mr. Willowby|
|1997||Danger Zone||Jim Scott|
|One Night Stand||Charlie|
|Two Girls and a Guy||Blake Allen|
|Hugo Pool||Franz Mazur|
|1998||''The Gingerbread Man||Clyde Pell|
|U.S. Marshals||Special Agent John Royce|
|1999||In Dreams||Vivian Thompson|
|Friends & Lovers||Hans|
|Black and White||Terry Donager|
|2000||Wonder Boys||Terry Crabtree|
|Auto Motives||Rob||short subject|
|2001||Last Party 2000||documentary|
|2002||Lethargy||Animal therapist||short subject|
|2003||Whatever We Do||Bobby||short subject|
|The Singing Detective||Dan Dark|
|Charlie: The Life and Art of Charles Chaplin||documentary|
|2004||Eros (segment "Equilibrium")||Nick Penrose|
|2005||Game 6||Steven Schwimmer|
|Kiss Kiss Bang Bang||Harry Lockhart|
|Good Night, and Good Luck.||Joe Wershba|
|Hubert Selby Jr: It/ll Be Better Tomorrow||documentary|
|2006||The Shaggy Dog||Dr. Kozak|
|A Scanner Darkly||James Barris|
|A Guide to Recognizing Your Saints||Dito Montiel|
|Fur: An Imaginary Portrait of Diane Arbus||Lionel Sweeney|
|Lucky You||Telephone Jack|
|2008||Charlie Bartlett||Principal Gardner|
|Iron Man||Tony Stark/Iron Man|
|Tropic Thunder||Kirk Lazarus|
|The Incredible Hulk||Tony Stark||cameo|
|The Soloist||Steve Lopez||post-production|
|2009||Sherlock Holmes||Sherlock Holmes||filming|
|2010||Cowboys & Aliens||Zeke Jackson||pre-production|
|Iron Man 2||Tony Stark/Iron Man||pre-production|
|2011||The Avengers||Tony Stark/Iron Man||pre-production|
|1985-1986||Saturday Night Live||18 episodes|
|2000-2002||Ally McBeal||Larry Paul||15 episodes|
|2005||Family Guy||Patrick Pewterschmidt||voice, episode "The Fat Guy Strangler"|
|2001||Best Performance by an Actor in a Supporting Role in a Series, Mini-Series or Motion Picture Made for TV ("Ally McBeal")||Golden Globe|