In 2001, Reeves continued to explore and accept roles in a diverse range of genres. The first was a romantic comedy, Sweet November, a 1968 remake of the same name. This was his second collaboration with Charlize Theron; the film was met with a generally negative reception. Desson Thompson of The Washington Post criticized it for its "syrupy cliches, greeting-card wisdom and over-the-top tragicomedy", but commended Reeves for his likability factor in every performance he gives. Hardball (2001) marked Reeves' attempt in another sports comedy. Directed by Brian Robbins, it is based on the book Hardball: A Season in the Projects by Daniel Coyle. Reeves plays Conor O'Neill, a troubled young man who agrees to coach a Little League team from the Cabrini Green housing project in Chicago as a condition of obtaining a loan. Film critic Roger Ebert took note of the film's desire to tackle difficult subjects and baseball coaching, but felt it "drifts above the surface", and Reeves' performance was "glum and distant".
In 1999, Reeves starred in the critically acclaimed science fiction film The Matrix, the first instalment in what would become The Matrix franchise. Reeves portrays computer programmer Thomas Anderson, a hacker using the alias "Neo", who discovers humanity is trapped inside a simulated reality created by intelligent machines. Written and directed by the Wachowskis, Reeves had to prepare by reading Kevin Kelly's Out of Control: The New Biology of Machines, Social Systems, and the Economic World, and Dylan Evans's ideas on evolutionary psychology. The principal cast underwent months of intense training with martial arts choreographer Yuen Woo-ping to prepare for the fight scenes. The Matrix proved to be a box office success; several critics considered it to be one of the best science fiction films of all time. Kenneth Turan of the Los Angeles Times felt it was a "wildly cinematic futuristic thriller that is determined to overpower the imagination", despite perceiving weaknesses in the film's dialogue. Janet Maslin of The New York Times credited Reeves for being a "strikingly chic Prada model of an action hero", and thought the martial arts stunts were its most strongest area. The Matrix received Academy Awards for Best Film Editing, Best Sound Editing, Best Visual Effects, and Best Sound.
More InfoReeves made a foray into television films in 1986, including NBC's Babes in Toyland, Act of Vengeance and Brotherhood of Justice. He made his first motion picture appearances in Peter Markle's Youngblood (1986), in which he played a goalkeeper, and in the low-budget romantic drama, Flying. He was cast as Matt in River's Edge, a crime drama about a group of high school friends dealing with a murder case, loosely based on the 1981 murder of Marcy Renee Conrad. The film premiered in 1986 at the Toronto International Film Festival to a largely positive response. Janet Maslin of The New York Times describes the performances of the young cast as "natural and credible", with Reeves being described as "affecting and sympathetic".
More InfoReeves starred alongside Patrick Swayze, Lori Petty and Gary Busey in the action thriller Point Break (1991), directed by Kathryn Bigelow. He plays an undercover FBI agent tasked with investigating the identities of a group of bank robbers. To prepare for the film, Reeves and his co-stars took surfing lessons with professional surfer Dennis Jarvis in Hawaii. Reeves had never surfed before. Upon its release, Point Break was generally well-received, and a commercial success, earning $83.5 million at the box office. Reeves' performance was praised by The New York Times for "considerable discipline and range", adding, "He moves easily between the buttoned-down demeanor that suits a police procedural story and the loose-jointed manner of his comic roles". Writing for The Washington Post, Hal Hinson called Reeves the "perfect choice" and praised the surfing scenes, but opined "the filmmakers have their characters make the most ludicrously illogical choices imaginable". At the 1992 MTV Movie Awards, Reeves won the Most Desirable Male award.
More InfoAfter the success of The Matrix, Reeves avoided another blockbuster in favour of a lighthearted sports comedy, The Replacements (2000). He agreed to a pay cut to enable Gene Hackman co-star in the film. Against his wishes, Reeves starred in the thriller The Watcher (2000), playing a serial killer who stalks a retired FBI agent. He said that a friend forged his signature on a contract, which he could not prove; he appeared in the film to avoid legal action. Upon its release, the film was critically panned. That year, he had a supporting role in another thriller, Sam Raimi's The Gift, a story about a woman (played by Cate Blanchett) with extrasensory perception asked to help find a young woman who disappeared. The film grossed $44 million worldwide. Film critic Paul Clinton of CNN thought the film was fairly compelling, saying of Reeves' acting: "[Raimi] managed to get a performance out of Reeves that only occasionally sounds like he's reading his lines from the back of a cereal box."
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