Inside Robert Downey Jr.'s Unbelievable Hollywood Comeback, From Jail to Winning an Oscar

Hollywood couldn't have scripted it better.

When Robert Downey Jr. heard his name announced—as expected—at the 2024 Oscars on March 10, he was receiving more than a Best Supporting Actor honor for disappearing into the role of Lewis Strauss in Oppenheimer, which dominated the night with seven wins, including Best Picture.

But as Downey himself acknowledged in some way or another every time he was on a stage this year, his juggernaut of an awards season was also a career achievement honor, a warm hug from the industry, a tangible sign of appreciation for the fact that he's still here.

"This is more of a most-improved player thing," he cracked in January at the Golden Globes. And at the SAG Awards, he offered coyly, "Why me? Why now? Why do things seem to be going my way?"

He kicked off his latest charming AF acceptance speech Sunday by thanking his "terrible childhood" and the Academy "in that order," and ultimately dedicated his win to his kids—30-year-old son Indio (with ex-wife Deborah Falconer) and son Exton, 12, and daughter Averi, 9 with wife Susan Downey. In between, the 58-year-old notably shouted out his entertainment lawyer Tom Hansen, for spending half of their 40 years together "trying to get me insured and bailing me out of the hoosegow."

And that means prison, for anyone who was wondering.

Though now it feels like we're talking about somebody else from a different timeline in the multiverse, Downey was in and out of jail between 1996 and 2001, including a year he spent between August 1999 and August 2000 in the hoosegow (actually the California Substance Abuse Treatment Facility and State Prison, Corcoran, or SATF at Corcoran II) after violating his probation from a June 1996 cocaine and weapon possession case by missing a drug test.

Charges that actually were not related to the July 1996 night he infamously passed out in an obliging bedroom after walking into the wrong house in Malibu. Though he was arrested for trespassing and being under the influence of a substance, the owner of the home was reluctant to press charges, telling the Los Angeles Times, "This is a nice guy who has troubles. It was a very unfortunate incident, whatever caused the problem. We hope he gets better." 

Quite the indicator of just how much people have been rooting for Downey since the beginning. From when he first flashed his star appeal in '80s movies like The Pick-Up Artist and Less Than Zero, to when he earned his first Oscar nomination—Best Actor for Chaplin—in 1993 when he was only 27, and all the way through when he filmed both U.S. Marshals and In Dreams while on furlough from jail in 1997 (the first time he violated probation from his June 1996 bust), the man has worked.

It's impossible to know where all this legal trouble would've landed Downey in the social media age, but who wants to know? (The Internet is incensed enough because he seemingly snubbed presenter Ke Huy Quan at the Oscars. P.S. They hugged a minute later, it was fine.) Point being, Downey's good days amid his struggles earned him enough credit among his peers (if not from insurance companies) that the chances kept coming, until he eventually got healthy enough to make his own luck.  

Which, incidentally, did not happen until after he got out of prison in August 2000, was arrested that November, won a Golden Globe in January 2001 for Ally McBeal, was arrested again that April, got fired from Ally McBeal and then spent nine months in court-mandated treatment and got clean for good.

Meeting his future wife Susan, a producer on his 2003 thriller Gothika, certainly helped his long-term prospects for success. ("She found me, a snarling rescue pet, and you loved me back to life," he said during his Oscar speech. "That's why I'm here.")

Yet though he made a bunch of movies in the aughts before joining the MCU, including Kiss Kiss Bang Bang, Zodiac and Good Night, and Good Luck, Downey wasn't joking about the struggle to get insured.

Lamenting the "cheap speed skaters" who prevented him from doing a Woody Allen movie at the time, Downey told The New York Times in 2003, ''But it's really all my fault if I want to think about it for half an hour.''

Business Insider has estimated that Downey made $435 million playing Tony Stark/Iron Man over the course of his MCU run, starting with $2.5 million for 2008's Iron Man and finishing with a base salary of $75 million for his explosive Avengers: Endgame exit in 2019.

But in the beginning, Marvel wanted no part of him and director Jon Favreau had to fight like hell to get him into consideration. Which was ultimately a rather worthwhile struggle, but there's definitely a before and an after when it comes to this chapter of Downey's life. 

"Right now, my BlackBerry is literally overloading and crashing, and the phone is never not ringing," he told Rolling Stone in 2008 in the wake of Iron Man's $575 million global showing at the summer box office. "It's crazy. Like a Super Bowl. Like a landslide. Like nothing I've ever experienced."

He shot Tropic Thunder right after Iron Man, earning his second Oscar nomination and first for Best Supporting Actor in 2009. And while he's presumably since switched to an iPhone, he's been the RDJ the millennials know and love ever since. (Incidentally, then-California Gov. Jerry Brown pardoned Downey in 2015, his office explaining that the actor had since "lived an honest and upright life, exhibited good moral character, and conducted himself as a law-abiding citizen.")

When Downey noted in his Oscar speech that he "needed this job more than it needed me," some of the Internet speculated that he was dissing the MCU—which, Angela Bassett's Golden Globe win and Oscar nomination for Black Panther: Wakanda Forever aside, is known less for producing rich, multilayered performances than it is for keeping actors busy for years with demanding shooting schedules.

But from here it sounded like the self-aware star was acknowledging that his post-MCU passion project, 2020's Dolittle, didn't really work out, and he had simply been searching for the right role.

In the meantime, the 2022 Netflix documentary Sr., about the actor's filmmaker father Robert Downey Sr., that he laboriously shepherded into being was very well-received. (In the film, the elder Downey, who died in 2021, expressed regret for exposing his son to drugs at such a young age. As in, first passing his son a joint when the boy was 6 to be funny in front of his poker night buddies.) 

And for Downey, doing Oppenheimer—about the creation of the atomic bomb and what that meant for the entire world—made perfect sense. "For me," he explained during an actors roundtable for The Hollywood Reporter, "it was a logical thing from Sr. going back into, 'What is this thing that my dad's generation rebelled against?'"

He compared the massive production to "100 people making a watch together every day" and joked about finding out what sort of movie star treatment was available to him once he arrived on the set of the Christopher Nolan-directed epic.

"It's fun to realize what you're becoming accustomed to," Downey said. "'Like, OK, let's talk about my perks.' 'There are none.' 'OK, well, hold on a second here...'" Laughing, he mimicked Nolan with his English accent telling him, "'You can have $300 a day to spend it however you'd like.'"

Miming his own disbelief, Downey cracked, "I was like, 'That's my dry-cleaning budget!'" But getting serious, he added, "First of all, I think, maximum humility is where we get that spot [as actors], whether we can choose to do it or the situation requires. It's like, you should be scared, you should have approach anxiety to this, because this is real s--t. If you do it right." 

For the many times he did it right, and even for the times that he didn't, Downey is now an Oscar winner.

And what a night it was. See all the winners from the 2024 Academy Awards:

American Fiction
Anatomy of a Fall
Barbie
The Holdovers
Killers of the Flower Moon
Maestro
WINNER: Oppenheimer
Past Lives
Poor Things
The Zone of Interest

Annette Bening, NYAD
Lily Gladstone, Killers of the Flower Moon
Sandra Hüller, Anatomy of a Fall
Carey Mulligan, Maestro
WINNER: Emma Stone, Poor Things

Bradley Cooper, Maestro
Colman Domingo, Rustin
Paul Giamatti, The Holdovers
WINNER: Cillian Murphy, Oppenheimer
Jeffrey Wright, American Fiction

Emily Blunt, Oppenheimer
Danielle Brooks, The Color Purple
America Ferrera, Barbie
Jodie Foster, NYAD
WINNER: Da'Vine Joy Randolph, The Holdovers

Sterling K. Brown, American Fiction
Robert De Niro, Killers of the Flower Moon
WINNER: Robert Downey Jr., Oppenheimer
Ryan Gosling, Barbie
Mark Ruffalo, Poor Things

Anatomy of a Fall, Justine Triet
Killers of the Flower Moon, Martin Scorsese
WINNER: Oppenheimer, Christopher Nolan
Poor Things, Yorgos Lanthimos
The Zone of Interest, Jonathan Glazer

WINNER: The Boy and the Heron
Elemental
Nimona
Robot Dreams
Spider-Man: Across the Spider-Verse

Best International Feature Film

Io Capitano, Italy
Perfect Days, Japan
Society of the Snow, Spain
The Teachers' Lounge, Germany
WINNER: The Zone of Interest, United Kingdom

Bobi Wine: The People's President
The Eternal Memory
Four Daughters
To Kill a Tiger
WINNER: 20 Days in Mariupol

Best Documentary Short Film

The ABCs of Book Banning
The Barber of Little Rock
Island in Between
WINNER: The Last Repair Shop
Nǎi Nai and Wài Pó

The After
Invincible
Knight of Fortune
Red, White and Blue
WINNER: The Wonderful Story of Henry Sugar

Letter to a Pig
Ninety-Five Senses
Our Uniform
Pachyderme
WINNER: War Is Over! Inspired by The Music of John & Yoko  

Barbie
Killers of the Flower Moon
Napoleon
Oppenheimer
WINNER: Poor Things

"The Fire Inside," Flamin' Hot
"I'm Just Ken," Barbie
"It Never Went Away," American Symphony
"Wahzhazhe (A Song For My People)," Killers of the Flower Moon
WINNER: "What Was I Made For?," Barbie

American Fiction
Indiana Jones and the Dial of Destiny
Killers of the Flower Moon
WINNER: Oppenheimer
Poor Things

The Creator
Maestro
Mission: Impossible - Dead Reckoning Part One
Oppenheimer
WINNER: The Zone of Interest

Golda
Maestro
Oppenheimer
WINNER: Poor Things
Society of the Snow

Barbie
Killers of the Flower Moon
Napoleon
Oppenheimer
WINNER: Poor Things

WINNER: Anatomy of a Fall
The Holdovers
Maestro
May December
Past Lives

WINNER: American Fiction
Barbie
Oppenheimer
Poor Things
The Zone of Interest

The Creator
WINNER: Godzilla Minus One
Guardians of the Galaxy Vol. 3
Mission Impossible - Dead Reckoning Part One
Napoleon

Best Film Editing

Anatomy of a Fall
The Holdovers
Killers of the Flower Moon
WINNER: Oppenheimer
Poor Things

Best Cinematography

El Conde,
Killers of the Flower Moon
Maestro
WINNER: Oppenheimer
Poor Things