The Shocking Events That Put Robert Downey Jr. Behind Bars (More Than Once)
"I said, 'You know what? I don't think I can continue doing this.'"
Updated Aug. 6 2025, 5:01 p.m. ET

Thanks in large part to his big bet on Marvel, Robert Downey Jr. is one of the wealthiest actors in the history of Hollywood. RDJ's success is all the more remarkable, though, because of how far he's come in the years since he first showed up as Tony Stark.
Although RDJ's success seems inevitable now, there was a time when it looked like his career had totally fallen apart.
Now that he's an Oscar winner, let's examine how he ended up in legal trouble throughout much of the late '90s.

Robert Downey Jr. in 1996.
Why did Robert Downey Jr. go to jail?
The long and short of it is that, between 1996 and 2001, Robert was arrested several times on charges related to drugs, including cocaine, heroin, and marijuana. In that period, he was in and out of jail on more than one occasion, and relapsed several times as well.
He reportedly told a judge that he had been addicted to drugs since he was 8 years old because his father had given them to him.
In June of 1996, he was arrested in possession of heroin, cocaine, crack cocaine, and an unloaded .357 Magnum handgun while speeding down Sunset Boulevard. A month later, he wandered into a neighbor's house while high and fell asleep in one of their beds. They refused to press charges.
He eventually spent time in court-ordered rehab, but after missing a mandatory drug test in 1997, he spent six months in Los Angeles County jail.

Robert Downey Jr.'s mugshot in 2001.
He missed another required drug test in 1999 and was arrested again. Following this arrest, he was sentenced to a three-year prison term at the California Substance Abuse Treatment Facility and State Prison.
Ultimately, though, he only spent a year in the facility before he was released on bail. Just a week after his release, he joined the cast of Ally McBeal and was acclaimed for his performance.
Ultimately, though, he was arrested yet again and ordered to go to rehab for another year. It wasn't until 2001 that he began to seriously focus on recovery, ultimately springboarding his return to Hollywood.
In an interview with Oprah Winfrey in 2004, Robert explained that his 2001 arrest was a breaking point, and he realized he could no longer live his life as he had been.

"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," he explained. "You can reach out for help in kind of a half-assed way, and you'll get it, and you won't take advantage of it. It's not that difficult to overcome these seemingly ghastly problems ... what's hard is to decide to do it."
RDJ's lows were lower than almost any successful actor in the history of Hollywood.
But it's fair to say that, in the years since, he's reached the pinnacle of what Hollywood actors dream about.