Prolific in film since 1984, Reeves' most acclaimed and highest-grossing films, according to the review aggregate site Rotten Tomatoes, include: River's Edge (1987), Bill and Ted's Excellent Adventure (1989), My Own Private Idaho (1991), Much Ado About Nothing (1993), Speed (1994), The Matrix (1999), John Wick (2014), John Wick: Chapter 2 (2017), John Wick: Chapter 3 – Parabellum (2019), and Toy Story 4 (2019). Reeves' has won three MTV Movie Awards, and received two Best Actor nominations at the Saturn Awards. He was nominated twice for a People's Choice Award: Favorite Male Movie Star and Favorite Action Movie Star, for his performance in John Wick: Chapter 3 – Parabellum (2019).
On December 24, 1999, Reeves' girlfriend, Jennifer Syme, gave birth eight months into her pregnancy to Ava Archer Syme-Reeves, who was stillborn. The couple broke up several weeks later. On April 2, 2001, Syme was killed when her vehicle collided with three parked cars on Cahuenga Boulevard in Los Angeles. She was being treated for depression at the time, and police found prescription medication in her car. Reeves, who was scheduled to film The Matrix sequels the following spring, sought "peace and time", according to friend Bret Domrose of Dogstar.
More InfoRebecca Miller's The Private Lives of Pippa Lee was Reeves' sole release of 2009, which premiered at the 59th Berlin International Film Festival. The romantic comedy and its ensemble received an amicable review from The Telegraph's David Gritten; "Miller's film is a triumph. Uniformly well acted, it boasts a psychologically knowing script, clearly written by a smart, assertive human". In 2010, he starred in another romantic comedy, Henry's Crime, about a man who is released from prison for a crime he did not commit, but then targets the same bank with his former cellmate. The film was not a box office hit. Reeves' only work in 2011 was an adult picture book titled Ode to Happiness, which he wrote, complemented by Alexandra Grant's illustrations. Reeves co-produced and appeared in a 2012 documentary, Side by Side. He interviewed filmmakers including James Cameron, Martin Scorsese, and Christopher Nolan; the feature investigated digital and photochemical film creation. Next, Reeves starred in Generation Um... (2012), an independent drama which was critically panned.
More InfoAfter this series of commercial failures, Reeves career rebounded in 2014. He played the titular role in the action thriller John Wick, directed by Chad Stahelski. In the first instalment of the John Wick franchise, Reeves plays a retired hitman seeking vengeance. He worked closely with the screenwriter to develop the story; "We all agreed on the potential of the project. I love the role, but you want the whole story, the whole ensemble to come to life", Reeves said. Filmed on location in the New York City area, the film was eventually released on October 24 in the United States. The Hollywood Reporter was impressed by the director's "confident, muscular action debut", and Reeves' "effortless" performance, which marked his return to the action genre. Jeannette Catsoulis of The New York Times praised Reeves' fight scenes and noted he is "always more comfortable in roles that demand cool over hot, attitude over emotion". John Wick proved to be a box office success, grossing $86 million worldwide. Next, Reeves starred in a smaller-scale horror feature, Knock Knock (2015), a remake of the 1977 film Death Game. Described as "over-the-top destruction" by the Toronto Star, Reeves plays a father, home alone, when two young women show up and start a game of cat and mouse. His other releases in 2015 were the documentaries Deep Web, about crime on the dark web, and Mifune: The Last Samurai, about the life of a Japanese actor (Toshiro Mifune) famous for playing samurai characters. He narrated both films.
More InfoIn a 2005 article for Time magazine, Lev Grossman called Reeves' "Hollywood's ultimate introvert". He has been described as a workaholic, charming and "excruciatingly shy". During the production of Constantine, director Francis Lawrence commented on his personality, calling him "hardworking" and "generous". His co-star Shia LaBeouf said, "I've worked with him for a year and a couple of months, but I don't really know him that much". Erwin Stoff of 3 Arts Entertainment has served as Reeves' agent and manager since he was 16, and produced many of his films. Stoff said Reeves "is a really private person" and keeps his distance from other people.
More InfoReturning to the John Wick franchise, Reeves starred in John Wick: Chapter 3 – Parabellum (2019), the third feature in the series directed by Chad Stahelski. The film takes place immediately after the events of John Wick: Chapter 2 and features new cast members including Halle Berry. The film was another box office hit, grossing $171 million in the United States and more than $155 million internationally. The Globe and Mail's reviewer gave the film three out of four stars, praising the action choreography for not becoming boring, but felt there was "aesthetic overindulgence" with the cinematography. The Guardian's Cath Clarke questioned Reeves' acting–writing "he keeps his face statue-still", and added "three movies in, franchise bloat is beginning to set in". Reeves was nominated for Favorite Male Movie Star of 2019 in the People's Choice Awards, and the film itself was nominated for Best Contemporary Film in the Art Directors Guild Awards. Reeves had a cameo role in the Netflix original film Always Be My Maybe (2019), which he took on to highlight his Asian ancestry. He then voiced Duke Caboom in Toy Story 4 (2019), the fourth instalment of Pixar's Toy Story franchise. That same year, on April 27 and 28, a film festival was held in his honour, called KeanuCon, hosted in Glasgow, Scotland. Over two days, nine of his films were screened for guests.
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