At 5, Robert Downey Jr. – the son of director Robert Downey and actress Elsie Downey – makes his film debut playing a puppy in his father's film Pound. While his director father introduces him to acting, he also introduces him to marijuana as a kid. "When my dad and I would do drugs together," he says, "it was like him trying to express his love for me in the only way he knew how."
Downey falls for Firstborn costar Sarah Jessica Parker, and the couple soon moves in together. But the actor's drug use causes tension in their relationship. "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica," he later tells Parade. In 1991, Parker ends their seven-year relationship. "She tried to help me," he says. "She was so miffed when I didn't get my act together."
After briefly appearing on Saturday Night Live in 1985, Downey catches Hollywood's eye with star turns in The Pick-up Artist and Less Than Zero, in which he plays a junkie. Having shot the film at the height of his addiction, the actor later tells the Chicago Tribune, "I didn't know if art was imitating life, or what was imitating what."
After a 42-day courtship, Downey weds singer Deborah Falconer. "It was really her personality, though it was of great benefit that she happens to be one of the most drop-dead gorgeous women I'd ever seen," he tells Playboy in 1997 of their quickie wedding. On September 7, 1993, the couple welcomes a son, Indio.
Downey beats out A-listers Billy Crystal and Robin Williams to land the role of Charlie Chaplin in the biopic Chaplin. Though the film is a box office disappointment, it earns Downey a Best Actor Oscar nomination.
After separating from Falconer, Downey has several run-ins with the law for possession of heroin and cocaine, being under the influence and a bizarre incident in which he breaks into a neighbor's home. The actor, who spends nearly four months in prison in 1997, ends up serving another year in 1999 for another misstep. "You are actually in the safest place on Earth," he later says of prison. "Safe from the intruders."
Following his release from prison, Downey joins the cast of Ally McBeal, eventually earning a supporting actor Golden Globe for his performance as Larry Paul. However, the actor continues to struggle with sobriety, and following arrests that November and in April 2001, he is written off the show.
After completing a year at a live-in rehab facility, Downey is let off of probation. "It's going to be a long time before I can ever say, 'I'm well on the road to recovery,'" he says in court, "but this past year...there has been progress." The actor returns to work with roles in 2003's The Singing Detective and Gothika, where he meets and begins dating Hollywood producer Susan Levin.
With Levin, Downey takes another trip down the aisle. "[She] has got me in a freakin' choke chain, and I love it," the actor, who credits Levin for helping him clean up his act, says of his new wife. That same year, he stars in the comedy Kiss Kiss Bang Bang and George Clooney's Good Night, and Good Luck.
Downey returns to superstardom with the comic book blockbuster, Iron Man, which rakes in $98 million during its opening weekend. "Nobody appreciates this opportunity more," says director Jon Favreau. "To have another shot at this, after what he's had and lost, is as redemptive a story as the movie itself." That August, the actor takes a risk, donning "black face" for his role in Tropic Thunder, which earns him his second Oscar nomination.
BIOGRAPHY (top to bottom): Ron Galella/WireImage; Barry King/Wireimage; Everett; Ron Galella/WireImage; Everett; Splash News Online; FOX; Warner Bros.; Julie Skarratt/Landov; Zade Rosenthal/Marvel Entertainment