As a teen, he started attending the Stagedoor Manor Performing Arts Training Center just as his parents’ marriage broke down. After they split, his father moved to California and for several years, Downey Jr. bounced between the east and west coast until finally settling in with roommate, Kiefer Sutherland, in Hollywood for three years.
After taking on theater roles in off-Broadway shows, he was hired as part of a fresh, younger crew on Saturday Night Live. While the entire season was panned, Downey Jr., who was barely 20 at the time, was singled out by Rolling Stone as the worst SNL cast member in the history of the show.
Fortunately, while he narrowly missed being cast as Duckie in Pretty in Pink, he had other projects on the horizon and found his way into lighthearted ’80s classics such as Weird Science, Back to School, and The Pick-Up Artist.
“Chaplin” changed the game
With his credibility growing in the industry, Downey Jr. was trusted with meatier roles in films such as Less Than Zero, Air America, and Soapdish. His solid performances helped earn him the role that would fully establish him as an incredible actor.
Downey Jr. was given the opportunity to portray Hollywood icon, Charlie Chaplin, and he took the preparation very seriously. He learned to play the violin and tennis with his left hand, enlisted the help of a coach to perfect Chaplin’s signature walk and demeanor, and was even rewarded by being nominated for an Academy Award for his performance.
Failed relationships and fatherhood
During an appearance on the Howard Stern Show, Sarah Jessica Parker discussed seeing Downey Jr. so long after their eight-year relationship ended and explained, “It was really nice. It was surprisingly not weird [to get together]. I guess you spend so many years with someone ― we were 18 when we met ― and fundamentally we’re sort of the same. I think the difference is he has a family and a wife and obviously his career is a massive thing, but I think his true nature — it was completely familiar.”
When Downey Jr. was asked about the downfall of their romance, he openly admitted, “I was so selfish. I liked to drink, and I had a drug problem, and that didn’t jibe with Sarah Jessica, because it is the furthest thing from what she is. She provided me a home and understanding. She tried to help me. She was so miffed when I didn’t get my act together.”
Eventually, Downey Jr. moved on. After just 42 days of dating, he married singer/actress, Deborah Falconer, in 1992. Two years later, the couple welcomed their son, Indio Falconer Downey. Unfortunately, Downey Jr. ‘s stints in rehab and jail led to their divorce in 2004, with Falconer claiming custody of their son.
Between 1996 and 2001, Downey Jr. spent a lot of time in the company of law enforcement. With charges stemming from possession of marijuana, cocaine, heroin, and even a handgun the actor eventually explained to a judge in 1999, “It’s like I have a shotgun in my mouth, and I’ve got my finger on the trigger, and I like the taste of the gun metal.”
At one point, while under the influence, Downey Jr. entered a neighbor’s home and fell asleep in one of their beds. The court determined he needed to undergo regular drug testing while fulfilling three years of probation. When he missed one of the mandatory tests, he served six months in the Los Angeles County jail.
Sadly, Downey Jr. ‘s downward spiral only continued. After missing another drug test, he was sentenced to three years in prison at the California Substance Abuse Treatment Facility and State Prison in Corcoran, California. While he was allowed to finish filming In Dreams before reporting for incarceration, he was fired as the voice actor for the animated show, God, The Devil, and Bob.
Unexpectedly in 2000, after just a year in prison, he was released early after a judge determined that he had spent enough time behind bars. He posted $5,000 in bail and, a week later, was cast as a love interest on the hit show Ally McBeal.
Not surprisingly, his performance was acclaimed and he was not only nominated for an Emmy Award in the Outstanding Supporting Actor in a Comedy Series category but actually won a Golden Globe for Best Supporting Actor in a mini-series or television film. Unfortunately, Downey Jr. felt the praise was undeserved and said, “It was my lowest point in terms of addictions. At that stage, I didn’t give a [expletive] whether I ever acted again.”
Despite the fact that he was arrested over the 2000 Thanksgiving holiday weekend in his hotel room for drug possession, Ally McBeal producers planned to extend his appearances on the show since he had boosted the sagging ratings so much.