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The project achieved a worldwide box office take of 7 million.

Later that year, he starred in Jerry Zaks' family drama Marvin's Room, reuniting with Robert De Niro.

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.

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.

Budgeted at $US50 million, the film became a financial success, grossing $US144 million worldwide, Todd Mc Carthy of Variety noted that "Richard [Di Caprio's role] is too much the American Everyman and not enough of a well-defined individual to entirely capture one's interest and imagination, and Di Caprio, while perfectly watchable, does not endow him with the quirks or distinguishing marks to make this man from nowhere a dimensional character." Di Caprio's first film of 2002 was the biographical crime drama film Catch Me If You Can, based on the life of Frank Abagnale Jr., who, before his 19th birthday, used his charm, confidence, and several different personas, to make millions in the 1960s writing bad checks.

Since 2000, Di Caprio has received critical acclaim for his work in a wide range of film genres.

Di Caprio's subsequent films include The Man in the Iron Mask (1998), the biographical crime drama Catch Me If You Can (2002), and the epic historical drama Gangs of New York (2002), which marked his first of many collaborations with director Martin Scorsese.

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 auditionees.

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.

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Di Caprio's portrayals of Howard Hughes in The Aviator (2004) and Hugh Glass in The Revenant (2015) won him the Golden Globe Award for Best Actor – Motion Picture Drama, and his role as Jordan Belfort in The Wolf of Wall Street (2013) won him the award for Best Actor – Motion Picture Musical or Comedy.

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