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c. 1985-86

Robert Downey, Jr., age 20, on Saturday Night Live

He's been the highest paid actor in Hollywood. He's also been at rock bottom.

Yes, there was a senior. But when it comes to the name “Robert Downey,” it’s likely you think only of the younger of the two. A man now known best for being clad in iron, Robert Downey, Jr. has been the highest paid actor in Hollywood. He’s also been right at rock bottom.

Robert Downey Jr
Al Levine/NBCU Photo Bank/Getty Images

On screen since the age of five, Downey made his debut in 1970, when he played a sick puppy in one of his father’s films. Downey’s struggles with drug addictions are well documented. But what is less known is that his father was also a drug addict, and first introduced his son to marijuana at age six.

This set of pictures was taken when, at 20, Downey was hired by Saturday Night Live. But he only lasted a season, and has the honor of being Rolling Stone‘s “Worst SNL Cast Member of All Time.” (In discussing the Downey sketch “Suitcase Boy,” Rolling Stone said it “originated from some parallel dimension where skits aren’t supposed to be funny.”)

Gradually, Downey’s career picked up, moving from off-Broadway to Broadway to cinema. The trajectory was positive, and took him, in 1992, all the way to the title role in Chaplin, for which he was nominated for an Academy Award. What could possibly go wrong?

Robert Downey Jr
Al Levine/NBCU Photo Bank/Getty Images

Downey went wrong.  As he told a judge in 1999, after one of the many drug arrests he faced during the 90s, “It’s like I have a shotgun in my mouth, and I’ve got my finger on the trigger, and I like the taste of the gun metal.” Downey spent more than a year living in a drug rehab center.

The turnaround started in 2001 with, improbably, an acting role in an Elton John video. Gradually Downey found himself back on the big screen — though producers weren’t taking chances. One withheld 40% of Downey’s salary until shooting was complete, and that became standard practice for anyone hiring him.

RM Lewis Jr./NBCU Photo Bank/Getty Images
RM Lewis Jr./NBCU Photo Bank/Getty Images

Then came 2008’s Iron Man. Suddenly Saturday Night Live seemed a very long time ago — although, in the shot above, with Downey in a silver-suit, it seemed strangely prophetic.

Robert Downey Jr. and Randy Quaid
RM Lewis Jr./NBCU Photo Bank/Getty Images
Jon Lovitz, Madonna, Damon Wayans, Robert Smigel, Robert Downey Jr.
Alan Singer/NBCU Photo Bank/Getty Images
Terry Sweeney, Jon Lovitz, Joan Cusack, Robert Downey Jr.
RM Lewis Jr./NBCU Photo Bank/Getty Images
Robert Downey Jr.
NBC/NBCU Photo Bank/Getty Images
Randy Quaid, Robert Downey Jr.
Alan Singer/NBCU Photo Bank/Getty Images
Terry Sweeney, Robert Downey Jr., Randy Quaid
NBC/NBCU Photo Bank/Getty Images

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