Annual earnings: $75 million
Biggest flop: Friends & Lovers (1999)

Twenty years ago, Robert Downey Jr. was one of Hollywood's most in-demand actors, and a first-time Oscar nominee for his role in Chaplin. A decade later, he was better known for his multiple drug and alcohol-related arrests and failed attempts at rehab. Though he continued acting throughout these troubled times, he wasn't the first choice on any studio executive's list of leading men. Which would explain why he’d agree to take a role in Friends & Lovers—and give Stephen Baldwin top billing!

(Barely) released in 1999, Friends & Lovers is a poorly made romantic-drama about a group of friends who spend a weekend skiing, talking, and talking some more in Park City, Utah. In his review of the film, Roger Ebert stated that: “I don't want to review Friends & Lovers, I want to flunk it. This movie is not merely bad, but incompetent. I get tapes in the mail from 10th graders that are better made than this.”

Audiences clearly weren’t interested either. The film's total box office take? $33,543—about .06 percent of what Downey cleared just on a supporting role in The Avengers. Talk about full circle!