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However while working on Growing Pains, Leo had auditioned for the lead in 'This Boy's Life', a disturbing, gritty, R-rated movie based on the life of writer Tobias Wolff. Whilst Leo didnt have much acting experience under his belt, after seven auditions Leo beat hundreds of actors for the role. At the time Leo admits, "It was like winning the lottery".Though Leo's natural, brilliant performance in this "coming of age" movie didn't hit home at the box office, he gained instant recognition as a young talented rising actor.

Leo follwed up his role in 'This Boy's Life' with the quirky character-driven drama 'What's Eating Gilbert Grape' (1993) Acting as Arnie, the mentally and physically challenged hyperactive younger brother of Gilbert Grape, played by Johnny Depp. Leo's reviews were brilliant with many magazines stating that Leo was "exasperatingly heartbreakingly real" and that his performance would "take your breathe away".

On the heels of the challenging but little seen 'This Boy's Life' and the accolade-reaping but little seen 'What's Eating Gilbert Grape' Leo was offered a part in the Western 'The Quick and the Dead'. It was to be his first big-budget movie. For that reason alone Leo nearly didnt take the part and most say he probably shoul'nt have. The film was a total flop at the box office and quickly yanked from theaters.

Soon, however, his luck was to change. His next film was 'Basketball Diaries' where he played a character named Jim Carroll - a real life 70's self-destructive teenager rebel turned poet and musician, alongside other actors such as Marky Mark (Yes thats right..from Marky Mark and the funky bunch). Leo's acting reviews were again brilliant and although the film came out with an R-rating Leo stated, "For a person my age (20 at the time) this is one of the best stories around".

Following 'Basketball Diaries' was the modest hit 'Marvin's Room' which allowed Leo the opportunity to act alongside two of America's finest actresses, Meryl Streep and Diane Keaton. However one of Leo's biggest breaks which lead to his worldwide recognition was his choice to star in the film 'Romeo and Juliet'. Never much of a student of the classics, Leonardo areed to play the lead in William Shakespeares 'Romeo and Juliet' only after being assured of two conditions. One, he would have a say in the actress cast as Juliet and secondly, that he wouldnt be playing a retro Romeo, but a cutting-edge hero. Leo wasnt interested in filming a traditional adaption, 'This would be a more wild, interesting version", he felt.

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