Young Robert Downey Jr.: A Look at His Dramatic Hollywood Journey From Bad Boy to Three-Time Oscar Nominee

Robert Downey Jr. is one of the most popular and acclaimed actors around, and his tumultuous journey through Hollywood has led to an inspiring story of redemption. The actor, who rose to prominence as a Brat Pack adjacent bad boy in the '80s and battled personal demons, had an amazing resurgence in the '00s as Marvel's Iron Man.

Currently, Downey is the frontrunner for the Best Supporting Actor Oscar for his role as antagonistic government official Lewis Strauss in Oppenheimer. He was previously nominated for playing a real-life actor, Charlie Chaplin, in the biopic Chaplin and a ridiculously over-the-top made-up actor in the satirical comedy Tropic Thunder. He has some serious range, and possesses a distinctive charisma that comes through in all his roles. Here's a look back at young Robert Downey Jr. in his cool-guy '80s days.

Destined for stardom

Young Robert Downey Jr. was exposed to the moviemaking world from childhood. His father, Robert Downey Sr., was a director known for his provocative low-budget films. In 1970, at just 5 years old, Downey Jr. made his screen debut in his dad's film Pound. He then appeared in two more of his dad's movies as a kid, and by the '80s, he started to pursue an acting career on his own terms.

In 1983, at 18, he had a small role in Baby It's You, and the next year, he appeared in the film Firstborn, which also featured a young Sarah Jessica Parker. The rising stars started dating, and would be a fashionable '80s power couple until they broke up in 1991.

Related: Young Sarah Jessica Parker: Take a Look Back at the Stylish Star’s Career Before ‘Sex and The City’

1985 was a busy year for Downey. His profile rose as he appeared in Tuff Turf, playing James Spader's friend, and Weird Science, playing a bully. He also joined the cast of Saturday Night Live, for a single infamous season in which the show underwent an ill-fated revamp.

Related: ‘Blacklist’ Star James Spader Then & Now: How He Became The Guy We Love to Hate

In 1986, Downey appeared in the comedy Back to School. He then returned to his roots in two movies directed by his dad, America and Rented Lips. Downey had his first starring role in 1987, opposite Molly Ringwald in The Pick-Up Artist.

Related: Molly Ringwald Movies: A Look Back Through the ’80s Teen Icon’s Best Films

He also starred in Less Than Zero, a very '80s literary adaptation in which he played a drug addict. The role was a case of art imitating life, as Downey was struggling with addiction off-camera and would battle it for many years. In an interview with The Guardian, he said, "the 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."

As the decade continued, Downey appeared in the teen movie Johnny Be Good and the period piece 1969 in 1988. He then appeared in That's Adequate, a mockumentary, True Believer, a courtroom drama, and Chances Are, a rom-com, in 1989.

Young Robert Downey Jr. the '90s A-lister

As the '90s dawned, Downey appeared in Air America and Soapdish, and in 1992, he had one of his most impressive roles, starring in Chaplin. Downey went deep to play the silent film icon, working with movement and speech coaches and studying Chaplin's filmography intensely. As he described it, "Chaplin was an absolute gift and a real bear of a challenge... I employed every single way I could try to show up for that role." His hard work led to his first Oscar nomination, and while he didn't win, the role established him as a versatile leading man.

Following Chaplin, Downey acted in edgy movies like Natural Born Killers (1994), Two Girls and a Guy (1997) and One Night Stand (1997), period dramas like Richard III (1995) and Restoration (1995), and comedies like Only You (1994), Home for the Holidays (1995) and Friends & Lovers (1999).

While Downey was working steadily throughout the '90s, he still faced personal battles, and was arrested multiple times on drug charges. An arrest record could tank any actor's career, and Downey experienced a precipitous decline. He came back with a well-received role in Ally McBeal in 2000, only to be arrested again and get fired.

An impressive comeback

Gradually, Downey returned to acting, with roles in films both praised (Kiss Kiss Bang Bang; Good Night, and Good Luck; Zodiac) and reviled (Gothika, The Shaggy Dog). In 2008, he staged one of the most surprising comebacks in modern Hollywood when he starred in Iron Man, the first film in the Marvel Cinematic Universe that would come to dominate the box office. Downey brought humor and swagger to the role, and would play it in nine more movies, ending with Avengers: Endgame in 2019.

2008 was also the year of Tropic Thunder, which earned Downey his second Oscar nomination for his hilarious role. His performance in 2009's Sherlock Holmes was another success. The popularity of Iron Man was such that Downey's filmography was dominated by the Marvel universe for years, but Oppenheimer, with its real-life drama and philosophical questions, marks a departure and gives him an intense role that he disappears into.

Related: Christopher Nolan Movies, Ranked: 10 of the Filmmaker’s Most Impressive Works

There's no one else quite like Downey in Hollywood, and we think an Oscar win for Oppenheimer would be well-deserved — and we look forward to seeing where he goes next.

Read on for more of our favorite leading men!

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