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In 1992, Di Caprio 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.
He next had recurring roles in various television series, such as the soap opera Santa Barbara and the sitcom Growing Pains.
He debuted in his film career by starring as Josh in Critters 3 (1991).
The film was directed by Michael Caton-Jones and released in 1993.
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.
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.He next starred in Agnieszka Holland' Total Eclipse, which he co-lead with David Thewlis.The feature is a fictionalized account of the homosexual relationship between Arthur Rimbaud (Di Caprio) and Paul Verlaine (Thewlis).Di Caprio is the founder of his own production company, Appian Way Productions.He began his 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 by Mattel, which he considered his first role.