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The Devil's Advocate did well at the box office and garnered good reviews.The 1999 science fiction-action hit The Matrix, a film in which Reeves had a starring role, was a box office success and attracted positive reviews.He made news by refusing to take part in Speed 2: Cruise Control – despite the offered million paycheque, which would have been his largest to date – in favour of touring with his band and playing the title role in a 1995 Manitoba Theatre Centre production of Hamlet in Winnipeg, Manitoba.

After a few minor roles, Reeves received a sizeable role in the 1986 drama film River's Edge, which depicted how a murder affected a group of teens.

Following this film's critical success, he spent the late 1980s appearing in a number of movies aimed at teenage audiences, including the lead roles in Permanent Record and the unexpectedly successful 1989 comedy, Bill & Ted's Excellent Adventure, along with its 1991 sequel, Bill & Ted's Bogus Journey.

During the early 1990s, Reeves started to break out of his teen-film period.

He appeared in high-budget action films such as Point Break, for which he won MTV's "Most Desirable Male" award in 1992.

He later dropped out and did not obtain a high school diploma.

Reeves' first studio movie appearance was Youngblood (1986), in which he played a Québécois goalie.

He is one of the top three Hamlets [Lewis has] seen, for a simple reason: he is Hamlet." Reeves' choices after A Walk in the Clouds failed with critics and audiences.

Big-budget films such as the sci-fi action film Johnny Mnemonic and the action-thriller Chain Reaction were critically panned and failed at the box office, while indie films like Feeling Minnesota were also critical failures.

Reeves' career choices after Speed were eclectic: despite his successes, Reeves continued to accept supporting roles and appear in experimental films.

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