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Kelly was born in Newport News, Virginia, the son of Lane and Ennis Kelly. He won a scholarship to the University of Southern California to study at the USC School of Cinema-Television. He made two short films at USC, "The Goodbye Place" and "Visceral Matter", before graduating in 1997.

"Donnie Darko" was his first feature and was nominated for 21 awards, winning 11 of them, including a nomination for a Saturn Award. The film later ended up #2 on Empire magazine's list of 50 greatest independent films of all time, behind Quentin Tarantino's "Reservoir Dogs".

Kelly wrote the screenplay for Tony Scott's biographical crime thriller "Domino" (2005), and went on to write and direct the postmodern L.A. satire "Southland Tales" (2006) and the science-fiction mystery "The Box" (2009), inspired by "The Twilight Zone" episode "Button, Button". Although his three films differ considerably in setting and characters, they share similar themes of time travel, existentialism, and spirituality.

Kelly's particular filmmaking sensibilities can be traced back to his viewing of Terry Giliam's "Brazil" (1985), as told to author Robert K. Elder in an interview for his book "The Film That Changed My Life" (2011).

The commercial underperformance of Kelly's films has made it difficult for him to secure financing for other projects, and as such he has not directed a film since 2009. In 2016, filmmaker Kevin Smith said of Kelly: "He is insanely creative and is not unlike Christopher Nolan. But Nolan wound up in the Warner Bros. system where he got special handling, and he got a lot of money to make huge art films like "Inception". Richard can be one of our greatest filmmakers. He is right now, but just a lot of people don't realize it. He's still a kid, and someone needs to Nolan that kid."