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Director Lasse Hallström admitted he was initially looking for a less good-looking actor but finally settled on Di Caprio as he had emerged as "the most observant actor" among all who auditioned.
the film became a critical success, resulting in various accolades for Di Caprio, who was awarded the National Board of Review Award and nominated for both an Academy Award and a Golden Globe for his portrayal.
When Robb decided to expand the black-and-white film to feature length, however, Di Caprio and costar Tobey Maguire had its release blocked by court order, arguing that they never intended to make it a theatrical release, as it would have commercial value thanks to their stardom.
In 1996, Di Caprio appeared opposite Claire Danes in Baz Luhrmann's film Romeo Juliet, an abridged modernization of William Shakespeare's romantic tragedy of the same name, which retained the original Shakespearean dialogue.
He began his film career by appearing in several commercials and educational films, following his older stepbrother Adam Farrar into television commercials, and landing an ad at age 14 for Matchbox cars.
In 1990, Di Caprio got a break on television when he was cast in the short-lived series based on the movie Parenthood.
Di Caprio next starred in Total Eclipse, a fictionalized account of the homosexual relationship between Arthur Rimbaud and Paul Verlaine.
He replaced River Phoenix, who died during pre-production on the project.
Later in 1993, Di Caprio co-starred as the mentally handicapped brother of Johnny Depp's character in What's Eating Gilbert Grape, a comic-tragic odyssey of a dysfunctional Iowa family.
The performance has a sharp, desperate intensity from beginning to end." Di Caprio's first effort of 1995 was Sam Raimi's The Quick and the Dead, a western film.
Sony Pictures was dubious over Di Caprio's casting, and as a result, co-star Sharon Stone decided to pay the actor's salary herself.
Upon the success of Titanic, Di Caprio stated in 2000: "I have no connection with me during that whole Titanic phenomenon and what my face became around the world [...] I'll never reach that state of popularity again, and I don't expect to.
It's not something I'm going to try to achieve either." The following year, Di Caprio made a self-mocking cameo appearance in Woody Allen's caustic satire of the fame industry, Celebrity (1998).
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After Parenthood, Di Caprio had bit parts on several shows, including The New Lassie and Roseanne, as well as a brief stint on the soap opera Santa Barbara, playing the young Mason Capwell.