Annual earnings: $39 million
Biggest flop: Total Eclipse (1995)
Two years before he was boarding Titanic, Leonardo DiCaprio was playing poet Arthur Rimbaud in Agnieszka Holland’s Total Eclipse, about the French teen’s tempestuous relationship with his mentor/lover Paul Verlaine (David Thewlis). Audiences didn’t seem to care; the film took in just north of $330,000 at the box office. But it did see a slight uptick in video sales two years later, once DiCaprio had cemented his heartthrob status as Jack Dawson and his legion of female fans learned that Leo went full-frontal for this film.