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.
Rebecca 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 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."
More InfoIn 2013, Reeves starred in his own directorial debut, the martial arts film Man of Tai Chi. The film has multilingual dialogue and follows a young man drawn to an underground fight club, partially inspired by the life of Reeves' friend Tiger Chen. Principal photography took place in China and in Hong Kong. Reeves was also assisted by Yuen Woo-ping, the fight choreographer of The Matrix films. Man of Tai Chi premiered at the Beijing Film Festival and the Cannes Film Festival, and received praise from director John Woo. A wider, warm response followed suit; Bilge Ebiri of Vulture thought the fight sequences were "beautifully assembled", and Reeves showed restraint with the film editing to present the fighters' motion sequences. The Los Angeles Times wrote, "The brutally efficient shooting style Reeves employs to film master choreographer Yuen Woo-ping's breathtaking fights ... is refreshingly grounded and old-school kinetic", while Dave McGinn of The Globe and Mail called the film "ambitious but generic". At the box office, Man of Tai Chi was a commercial disappointment, grossing only $5.5 million worldwide from a budget of $25 million. Also in 2013, Reeves played Kai in the 3D fantasy 47 Ronin, a Japanese fable about a group of rogue samurai. The film premiered in Japan but failed to gain traction with audiences. Initial reviews were not positive, causing Universal Pictures to reduce advertising spending for the film elsewhere. 47 Ronin was a box office flop and was mostly poorly received.
More InfoIn 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 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.
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