Foster’s worries were well-founded. The following year was a period in which Downey kept getting in trouble with the law. Arrested three times in the summer of 1996, he was busted for (among other things) possession of cocaine and heroin. The frequency of his arrests quickly eviscerated his reputation, leaving former reps fearing the worst. Loree Rodkin, his one-time manager, told People that summer, “Every day I look in the newspaper, and I think that I am going to read Robert’s obituary.”
In 1997, he was sentenced to six months in prison because of a violation of his probation. (In the interim, he’d made headlines a few more times, including being arrested on a narcotics charge after he’d broken into a neighbor’s house and fallen asleep in a child’s bedroom.) The judge who sentenced Downey to the six-month term was Mira, who you may remember ruled a few years later that the actor go to prison for three years. Mira had watched Downey try and fail to turn his life around: Back in 1997, he told Downey, “I’m going to incarcerate you, and I’m going to incarcerate you in a way that’s very unpleasant for you. I don’t care who you are. What I care about is that there is a life to be saved from drugs.”
Downey was apologetic then as well, saying, “I don’t know why … the severity and the fear … of you, of death and of not being able to live a life free of drugs has not been enough to make me not continually relapse … again. I really need to do this, even if I don’t want to, I need to.”
Getting released early from prison after the 1999 sentencing didn’t do any good: He was arrested twice in the next year, leading to him being sent to a rehab facility. (It had not been Downey’s first such visit.) Around the same time, he won an Emmy after being cast on “Ally McBeal,” but he said in 2003, “I’m probably not the best person to ask about that period. It was my lowest point in terms of addictions. At that stage, I didn’t give a fuck whether I ever acted again.” And yet, there were great performances: He’s funny in “Bowfinger” and “Wonder Boys,” and there are those who think the 2003 cult classic “The Singing Detective” is the best thing he’s ever done.
But that was also the year he finally got serious about getting sober. His second wife, Susan, whom he met when she produced his film “Gothika,” gave him (in Downey’s words) an “ultimatum,” which started him down the road to staying clean. In his Winfrey interview, Downey admitted, “You think [overcoming addiction is] supposed to get more and more dramatic, it’s not a movie. It’s real life. For me, I just happened to be in a situation the very last time and I said, ‘You know what? I don’t think I can continue doing this.’ And I reached out for help and I ran with it, you know? … It’s really not that difficult to overcome these seemingly ghastly problems. … What’s hard is to decide.”