It was 1999, and Robert Downey, Jr., an Oscar-nominated actor, teetered on the edge of a chasm. If Superior Court Judge Lawrence Mira — who had seen Downey stand before him on several occasions — had taken mercy on him, he might be dead now; it’s a fact that the actor recognizes. But Mira had no mercy left to grant. Downey had used up the judge’s goodwill with a series of bad choices, and the judge no longer saw the benefit of court-mandated rehabs and facilities. “It’s like I’ve got a shotgun in my mouth, my finger on the trigger and I like the taste of gun metal,” Downey said, pleading his case to stay free of prison. “We tried rehabilitation, and it simply hasn’t worked,” the judge responded. With a slam of the gavel, Downey’s fate was decided… three years in prison. It was the culmination of missteps in the actor’s personal life, but it wasn’t the end of his troubles, nor was it the start. In The Family Downey was born into a showbiz family. His father, Robert Downey, Sr., was known as a maverick filmmaker, part of the underground scene. Downey, Sr.’s satirical takes on Hollywood and politics began in 1961, and he acted in and directed a number of films through the ’60s and ’70s, including 1970’s Pound, which featured the acting debut of a 5-year-old Robert Downey, Jr. The counter-culture of the times also contributed to what would become Downey, Jr.’s dangerous obsession with substances. When he was just 8 years old, his father introduced him to marijuana. The drug use between father and son would continue for some time. “There was always a lot of pot and coke around. When my dad and I would do drugs together,” Downey said in the 1988 book The New Breed, “it was like him trying to express his love for me in the only way he knew how.”

Downey, Jr. began settling into the Hollywood role he was seemingly destined for. At 17, he dropped out of school, left L.A. and trekked to New York to become a serious thespian. He starred in one season of Saturday Night Live and had a small role in the cult comedy classic Weird Science. In 1987, he filmed his breakthrough role in Less Than Zero, in which he played a drug-addled youth whose life was spinning out of control. “Until that movie,” Downey said, “I took my drugs after work and on the weekends. That changed on Less Than Zero. The role was like the ghost of Christmas Future. I became an exaggeration of the character.” Downey’s life began rotating in perilous fashion: He entered his first rehab in 1988. His manager at the time received the brunt of his frustration when he exited the rehab facility. “I couldn’t stand to see him demolish himself,” she told People in 1996. “And when he came out, he fired me for making him face it.” Still, the thespian continued to turn in great performances in films like Chances Are and Soapdish. In 1992, he married Deborah Falconer, and the two bought a place in Malibu. But Downey’s demons were clawing at him badly, and his binges became more and more pronounced. At 26, Downey would get his biggest role as Charlie Chaplin in the film Chaplin. Despite the film getting less than positive reviews, Downey’s performance was so strong that he received an Oscar nomination.

He followed that performance up with another riveting turn in Oliver Stone’s Natural Born Killers. Downey was mounting an offensive to be known as one of the best actors of his generation, seemingly adept at playing any kind of role. But behind the scenes, he was unraveling due to a substance abuse problem that was about to rear itself onto the front page of every entertainment publication. The Trouble With Robert It was 11:15 in the morning on June 23, 1996, when police noticed a black Explorer careening down the Pacific Coast Highway doing 20 MPH over the speed limit. When officers pulled the vehicle over, they discovered Robert Downey, Jr., high and with a car full of substances and a weapon; they found heroin, cocaine, crack, and a .357 magnum. He had been discovered, and his problems had become fodder for entertainment programs and publications everywhere. Downey posted the $10,000 bond to get out of jail, but less than three weeks later, another incident occurred. Inebriated, Downey walked into his neighbor’s home, went to an 11-year old’s bedroom, undressed and slipped into the bed to fall asleep. His neighbor didn’t recognize him when she pulled back the sheets to her son’s bed, and called the police when Downey wouldn’t respond.

In 1995, Downey had begun a steady intake of crack and heroin, but it wasn’t as though no one was trying to help the falling actor. Sean Penn and Dennis Quaid allegedly drove him down to Arizona to spend time in a treatment facility — this was before the arrest with the unloaded gun — but Downey left after a few days and hitchhiked his way back home. When he returned, police arrested him for driving his Porsche in the nude. After Downey was detained following the incident at his neighbor’s home, he was court-mandated to attend a rehab facility. On July 20, 1996, Downey escaped from the facility through a bathroom window. Security tracked him down and hauled him off to jail. Several days later, he stood before Judge Mira, who placed the actor on probation and mandated a supervised stay in a treatment facility. For a short time, it almost seemed like he finally would get it. He hired sobriety coaches, went back to working on films, and took regular drug tests, which he passed. After skipping one test, though, Downey found himself back in jail, this time for 113 days. The stay would prove to be a brutal affair for the actor, as he allegedly woke up in a pool of his own blood after being targeted by the inmates; he would require surgery on his face. After his release, Downey would skip three drug tests, and by 1999, he found himself in front of Judge Mira once again. This time, the judge’s patience had run dry. For violating his parole on several occasions, Downey was sentenced to 36 months in prison, the same prison that housed Charles Manson. He would serve less than 12 months in the penitentiary, but it was a lesson that Downey was ready to absorb, even though his road to redemption would come with a few more bumps. Resurrection “There’s no way to explain how spiritually debilitating it is to be taken out of the loop of your life. It’s like dying,” Downey told NBC News from prison. It seemed like Downey was ready to get back to work following his release in 2000, but even successful resurrections have trouble getting off the ground. He was offered an eight-episode arc on the popular series Ally McBeal for the sum of $500,000. Downey did great in the role, even scoring a Golden Globe for his performance, but something dark was still scratching around inside Downey. His marriage was failing, and with his depression at a high, he found himself in a hotel room with the substances that had derailed his life. In November of 2000, police received a 911 call that there was someone in a hotel room with drugs and a gun, and that they were unstable. When officers responded to the call, they found Downey with four grams of cocaine and methamphetamine. He was subsequently fired from Ally McBeal. “For some folks it’s just a function of age,” Downey told Vanity Fair last year. “It’s perfectly normal for people to be obsessive about something for a period of time, then leave it alone.” But Downey wasn’t ready to “leave it alone” just yet. He awaited another trial, and as prosecutors deliberated with his legal team, Downey was arrested yet again in 2001. With few Hollywood production companies looking to insure the actor, his work slowed down, and he entered a drug-treatment facility for one year. He was struggling to get sober, but his marriage had already strained itself to its brink: His wife filed for divorce. Still, Downey remained optimistic and doing his best to work his way back to the top. In 2003, he starred in The Singing Detective, for which he received rave reviews. He starred in Gothika, Eros, A Scanner Darkly, and by 2005, it seemed like the man was on his way back. Also in 2005, he married his second wife, Susan, whom he credits with helping save him.