The movie that broke Robert Downey Jr’s heart: “It was going to be my coming-out party”

In the early 2000s, Robert Downey Jr began the road to recovery, which led to his becoming the biggest movie star in the world in his 40s.

The prodigiously talented actor spent much of the ’90s high on drugs, embroiled in scandal, and in trouble with the law, but after yet another stint in court-ordered rehab in 2001, he emerged determined that enough was enough. Over the next seven years, he rebuilt his reputation, married the love of his life, and completed an unlikely comeback with 2008’s Iron Man. Interestingly, though, he believed an earlier movie was supposed to be his reintroduction to the Hollywood A-list – and when it died at the box office, he was heartbroken.

In truth, the story of Downey Jr’s comeback began with a false start. In 2000, he was given a chance at redemption when he was cast in the uber-successful legal comedy-drama Ally McBeal. His performance nabbed him an ‘Outstanding Supporting Actor in a Comedy Series’ Emmy nomination. However, he wound up only working on the show for eight months after a pair of high-profile drug-related arrests forced producers to fire him.

Downey Jr spent a year in a rehabilitation facility after letting yet another chance for redemption slip through his fingers. When he was released, he was determined to change things but was unemployable in Hollywood and on the brink of filing for bankruptcy. He told Oprah Winfrey, “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.”

However, proving to Hollywood that he could now be trusted wasn’t an easy road. Even though Downey Jr got himself clean, no producer would hire him, and it took Mel Gibson paying his insurance bond out of his own pocket on 2003’s The Singing Detective to get the star back in the game. That same year, he starred in Gothika with Halle Berry after signing a contract with producer Joel Silver that would become standard over the next few years. In essence, he had to defer 40% of his salary until production wrapped with no incident.

Interestingly, Silver helped Downey Jr nab his next big gig – and the resurgent star saw this as the big one. He was hired as the lead in the Shane Black neo-noir black comedy Kiss Kiss Bang Bang, the famed Lethal Weapon screenwriter’s first stab at directing. The film was a two-hander with the late Val Kilmer – another troubled star in need of a comeback in the mid-2000s – and was released to rave reviews. Unfortunately, these reviews didn’t translate into ticket sales, and Kiss Kiss Bang Bang barely managed to scrape back its budget at the box office.

“It was going to be my coming-out party, my emergence into 21st-century cinema,” a crestfallen Downey told Entertainment Weekly in 2008. “When it tanked, I was heartbroken.”

There was a silver lining to Kiss Kiss Bang Bang flopping, though – a pretty massive one, in fact. While he was reeling from, in his opinion, the “best film I’ve ever done” failing to find an audience, he discovered that at least one crucial person had seen and loved it. “It wound up being a calling card,” Downey Jr revealed in 2020. “It came out, and it bombed, but Jon Favreau saw it, and he said, ‘This guy could do an action movie.’ And so that wound up being my calling card into the Marvel Universe.”

Indeed, Favreau was looking for an outside-the-box pick to play the charming weapons dealer turned metal-suited superhero Iron Man, and he became convinced Downey Jr was his man after watching his insanely charismatic turn in Kiss Kiss Bang Bang. The rest, as they say, is history.

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