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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.
Di Caprio's debut film role was in the comedic sci-fi horror film Critters 3, in which he played the stepson of an evil landlord, a role that Di Caprio described as "your average, no-depth, standard kid with blond hair." Di Caprio made his big screen breakthrough in 1992, when he was handpicked by Robert De Niro out of 400 young actors to play the lead role in This Boy's Life adapted from Tobias Wolff's memoir of the same name.
He played opposite De Niro, who was acting as his stepfather, and Ellen Barkin as his mother.
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.Based on Scott Mc Pherson's screenplay adaptation of his own 1991 stage play of the same name, the film revolves around two sisters, played by Meryl Streep and Diane Keaton, who are reunited through tragedy after 17 years of estrangement.In 1997, Di Caprio starred in James Cameron's Titanic (1997) as twenty-year-old Jack Dawson, a penniless Wisconsin man who wins two tickets for the third-class on the ill-fated RMS Titanic.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.