In 2005, Reeves played the titular role in Constantine, an occult detective film, about a man who has the ability to perceive and communicate with half-angels and half-demons in their true form. The film was a respectable box office hit, grossing $230 million worldwide from a $100 million budget but attracted mixed-to-positive reviews. The Sydney Morning Herald's critic noted that "Constantine isn't bad, but it doesn't deserve any imposing adjectives. It's occasionally cheesy, sometimes enjoyable, intermittently scary, and constantly spiked with celestial blatherskite". He next appeared in Thumbsucker, which premiered at the Sundance Film Festival in 2005. A comedy adapted from the 1999 Walter Kirn novel of the same name, the story follows a boy with a thumb-sucking problem. Reeves and the rest of the cast garnered positive critical reviews, with The Washington Post describing it as "a gently stirring symphony about emotional transition filled with lovely musical passages and softly nuanced performances".
In 1997, he starred in the supernatural horror The Devil's Advocate alongside Al Pacino and Charlize Theron. Reeves agreed to a pay cut of several million dollars so that the film studio could afford to hire Pacino. Based on Andrew Neiderman's novel of the same name, the feature is about a successful young lawyer invited to New York City to work for a major firm, who discovers the owner of the firm is a devil. The Devil's Advocate attracted positive reviews from critics. Film critic James Berardinelli called the film "highly enjoyable" and noted, "There are times when Reeves lacks the subtlety that would have made this a more multi-layered portrayal, but it's nevertheless a solid job".
More InfoIn 1989, Reeves starred in the comedy-drama Parenthood directed by Ron Howard. Nick Hilditch of the BBC gave the film three out of five stars, calling it a "feelgood movie" with an "extensive and entertaining ensemble cast". In 1990, Reeves gave two acting performances. He portrayed an incompetent hitman in the black comedy I Love You to Death, and played Martin, a radio station employee in the comedy Tune in Tomorrow. He also appeared in Paula Abdul's music video for Rush Rush which featured a Rebel Without a Cause motif, with him in the James Dean role.
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 InfoIn 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".
More InfoTowards the end of the 1980s, Reeves starred in several dramas aimed at teen audiences, including as the lead in The Night Before (1988), a comedy starring opposite Lori Loughlin, The Prince of Pennsylvania (1988) and Permanent Record (1988). Although the latter received mixed reviews, Variety praised Reeves' performance, "which opens up nicely as the drama progresses". His other acting efforts included a supporting role in Dangerous Liaisons (1988), which earned seven nominations at the 61st Academy Awards, winning three: Best Adapted Screenplay, Best Costume Design, and Best Production Design. This was followed by Bill & Ted's Excellent Adventure (1989), in which he portrays a slacker who travels through time with a friend (portrayed by Alex Winter), to assemble historical figures for a school presentation. The film was generally well-received by critics and grossed $40.5 million at the worldwide box office. Film review aggregator Rotten Tomatoes gave the film a 79% approval rating with the critical consensus: "Keanu Reeves and Alex Winter are just charming, goofy, and silly enough to make this fluffy time-travel Adventure work".
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