The True Triumph of Robert Downey Jr.’s Second Act

in less than two weeks, Robert Downey Jr. is probably going to win an Academy Award. He’s already taken home the Golden Globe and the SAG Award for his portrayal of Lewis Strauss, the man who decides to get revenge on J. Robert Oppenheimer, in Christopher Nolan’s acclaimed “Oppenheimer,” and there seems to be nothing standing in his way to claiming his first Oscar on March 10th. 

For anyone who has been a fan of Downey over the last several decades, his presumed win will be gratifying—a culmination of a career filled with ups and downs. But for those who remember, it may also be a surreal, poignant moment. Not that long ago, such a scene seemed impossible. It is not hyperbole to say that, at one point, many of us were scared that we’d lose one of the most talented actors of his generation. The Oscar will be deeply satisfying, but maybe not as much as the fact that, after so much struggle and scandal, Downey is in a good place. These stories tend to end in tears. His, happily, has not.

It has now been 25 years since Downey was arguably facing the darkest moment of his life. In the summer of 1999, he was sentenced to a three-year prison term, found guilty of drug and weapons possession. The actor’s addiction issues were well-documented by that point, but Downey’s attorney, Robert Shapiro, asked Judge Lawrence Mira for mercy, insisting Downey had changed. Mira was unconvinced, saying, “I don’t believe your client is committed to not using drugs. You may call that addiction. But there is some level of choice. I don’t think we have any alternative [to jail]. We have used them all.” In the courtroom, Downey described his addiction in vivid, harrowing fashion: “It’s like I’ve got a shotgun in my mouth, with my finger on the trigger, and I like the taste of the gun metal.”

Downey ended up serving only one year, but it was easy to imagine that the worst was yet to come. Whether before or after that 1999 sentencing, Gen-Xers had gotten accustomed to their heroes dying due to their demons: River Phoenix, Kurt Cobain, Philip Seymour Hoffman. In the early ‘90s, Downey had received a Best Actor nomination for “Chaplin,” a star on the rise, but the second half of that decade was littered with arrests and incidents—the kinds of things that make an actor seem like an out-of-control bad boy destined to do permanent harm to himself. You see it enough, and you get used to the patterns. Sadly resigned, you wait for the other shoe to drop.

His dependency issues had roots in his upbringing, just as his interest in acting had. In that courtroom in 1999, Downey said that he’d been addicted to drugs since he was eight. Downey’s father, independent filmmaker Robert Downey Sr., who had his own addiction battles, later admitted to letting his son smoke a joint when the boy was just six: “I knew I had made a terrible, stupid mistake … Giving a little kid a toke of grass just to be funny.”

The younger Downey had appeared in some of his dad’s movies as a kid, but he started garnering the world’s attention thanks to films like “Weird Science.” And then he was picked for “Saturday Night Live.” Downey and many of his fellow cast members were dismissed after one season. Sometimes, “SNL” makes bad decisions about who gets cut from the show—Downey would be the first to admit his firing was not one of those instances. “I learned so much in that year about what I wasn’t,” he’d say later. “I was not somebody who was going to come up with a catchphrase. I was not somebody who was going to do impressions. I was somebody who was very ill-suited for rapid-fire sketch comedy.” 

Still, Downey found the energy of live comedy exhilarating, adding, “You get a lot of cred just for being able to even participate in that level of real-time stress and excitement.”

By the late 1980s, he was a legitimate star, his good looks and smart-ass demeanor utilized in romantic comedies like “The Pick-up Artist” and “Chances Are.” (Considering his role in “Oppenheimer,” it’s amusing to point out that Downey played Albert Einstein in the 1989 mockumentary “That’s Adequate.”) But the most pivotal movie was “Less Than Zero,” an adaptation of the Bret Easton Ellis novel that saw him play Julian, a drug addict in a downward spiral. His performance was gripping, but Downey all-too-closely identified with the character. 

“Until that movie, I took my drugs after work and on the weekends,” he’d say later. “Maybe I’d turn up hungover on the set, but no more so than the stuntman. That changed on ‘Less Than Zero.’ … [T]he role was like the ghost of Christmas future. The character was an exaggeration of myself. Then things changed and, in some ways, I became an exaggeration of the character. That lasted far longer than it needed to last.”

Downey’s career continued to blossom in the 1990s: Beyond “Chaplin,” he was superb in Robert Altman’s ensemble piece “Short Cuts” and suitably unhinged in Oliver Stone’s combustible “Natural Born Killers.” On screen, he seemed willing to do anything—not bug-eyed crazed like Nicolas Cage but rippling with immediacy and unpredictability—but his drug use was increasingly becoming an issue. Sarah Jessica Parker, whose seven-year relationship with the actor ended in 1991, later admitted of their time together, “It taught me how I love and what’s the difference between loving and taking care of people and what’s necessary and what grown-ups should and shouldn’t do for one [another]. And maybe it taught me a little bit about being a parent, too, because … the way I cared for Downey were things that might be more suitable for a parent.” 

It wasn’t just girlfriends who were concerned: In an interview with Oprah Winfrey, Downey recalled working on 1995’s “Home for the Holidays,” director Jodie Foster taking him aside and saying, “You know you’re doing great on this film, and I know that you’re loaded, too. … I’m worried about you. Not on this one, because we’re almost done and you’re going to be okay, and I know you have a really strong work ethic and you’re kind of like a lab rat. You’re really resilient. That’s not a good thing in this situation. I’m worried about you for the next movie.”

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 a Golden Globe 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.”

I’m lucky never to have dealt with addiction, or to have anyone close to me who has, so I can’t pretend to know how complicated sobriety can be. But even so, I imagine it was much more challenging than Downey lets on. What’s undeniable is that, since getting sober in 2003, his career rebounded, even reached new heights. Whether it’s the R-rated crime comedy “Kiss Kiss Bang Bang” or his role in the stirring drama “Good Night, and Good Luck,” he suddenly conveyed a weightier presence than he’d shown in his younger years. His turn as “Zodiac’s” haunted investigative reporter Paul Avery is arguably his finest hour — Downey’s trademark sardonic humor mixing with something far bleaker and emotional — and he’s a hoot in “A Scanner Darkly,” tapping into that dark comedy’s paranoid vibe. 

But no movie of that era—not even “Tropic Thunder,” which earned him his second Oscar nomination and spurred ongoing debate about whether his satiric blackface performance was inappropriate—defined his comeback more than 2008’s “Iron Man.” Released the same summer as Nolan’s “The Dark Knight,” the other comic-book movie that changed the industry, “Iron Man” was no sure thing, with Downey (not that far removed from his legal issues) hardly an A-list superstar. But director Jon Favreau stuck by him, and the two men helped make the Marvel Cinematic Universe the biggest thing in Hollywood. There was a period when Downey was practically unemployable. (Mel Gibson, his “Air America” co-star, put up the money to help insure Downey for “The Singing Detective,” a favor that—no matter Gibson’s many abhorrent acts—has kept Downey forever grateful to his friend.) But now, all of a sudden, Downey was cinema’s most important star.

Flash-forwarding to today, when superhero fatigue is starting to feel permanent, it can be hard to appreciate how meaningful Downey was to the MCU. Ironically, years earlier, “SNL” had hired him and others in the hopes that established actors would help revitalize the struggling show—in a sense, that’s what Downey actually did for Marvel, giving it an instant legitimacy. When other Oscar nominees (like Mark Ruffalo) or respected indie stars (such as Scarlett Johansson) started signing up for the MCU, it wasn’t so shocking. Alongside Nolan’s Batman films, which had earned Heath Ledger a posthumous Oscar, the Marvel films sought the best actors in the world to sell the drama within the blockbuster spectacle. 

But other actors came and went in superhero movies. Some, like Chris Evans, openly lamented the demands of stardom. Not Downey: From “Iron Man” to his heroic death in 2019’s “Avengers: Endgame,” he was front and center. At MCU premieres, he always spoke last. He was the team captain. It wasn’t simply Tony Stark’s death that irrevocably changed the franchise’s future—it was the fact that Robert Downey Jr. wasn’t part of the MCU anymore that made the difference. Those movies’ heart—their upstart energy—was gone. Five years later, Kevin Feige is still trying to find a worthy replacement. 

Since exiting the MCU, Downey has kept working, never badmouthing the Iron Man years but also wanting to create a little distance. As he once put it, “I am not my work. I am not what I did with that studio. I am not that period of time that I spent playing this character.” Some of those post-Marvel projects have been disastrous—even on a bet, avoid “Dolittle”—but others were clearly personal. 

Working with prolific documentarian Chris Smith (“American Movie,” “Jim & Andy: The Great Beyond”), Downey decided to make a tribute to his father. “Sr.” chronicled Robert Downey Sr.’s filmmaking career, but its most affecting moments came from the two men simply talking, the son asking his dad about his life. There’s no grand catharsis—no moment of riveting candor in which they tearfully hash out their shared battles with addiction—but it’s clear that part of their bond was formed by what Sr. had introduced into Jr.’s world by giving him that joint so long ago. Downey Sr., who has Parkinson’s in the film, died in 2021, more than a year before the documentary’s release, and “Sr.” feels like a melancholy farewell to a father from his boy, who struggled as much as the old man with demons. But it also feels like the closing of a chapter for Downey, with a new one about to be written.

“Oppenheimer” was the first movie Downey made after his dad’s passing, his connection to some of the film’s New Mexico locations stemming from spending time there with his dad when he was a teenager. After working on the documentary and taking an acting hiatus, Downey got back in front of the camera to play a man so unlike himself—or, at least, the men he usually portrays. Strauss is deeply insecure and petty, his arrogance belying his smallness. Lacking any sense of humor, Strauss is the villain, the Salieri trying to take down his personal Mozart. Where Downey’s characters tend to be highly verbal, almost hyperactive, Strauss was hushed, unanimated. Tony Stark was triumphant—Lewis Strauss is humiliated in the most public fashion imaginable. Robert Downey Jr. returned to cinemas, but he wasn’t the man we remembered.