Chris began making films at the age of 13. Some of his works were well known in the Tampa Bay area, where he went to high school. The film Palm Harbor Vice (1991) (a Miami Vice (1984) parody) was a cult hit and received local media attention. The sequel, Palm Harbor Vice 2: Brotherhood of the Monkey (1993) earned Flynn an award for "Best Original Teleplay" at the 1996 Time Warner Spotlight Achievement Awards. Chris, followed up the films with The Epic of Detective Mandy: Book One - Satan Claus (1989) , a five part series of teleplays about monsters and zombies in a small town. The series was a cult hit, with a large following for the television broadcasts, as well as bootleg tapes circulating throughout the State of Florida.

To pay his way through film school, Chris began working overnights at The Home Shopping Network in the early 1990s (going to school during the day). He has since filled roles as technical director, director, editor, robotic cameras operator, audio mixer, and chyron graphics operator for companies such as: E! Entertainment Television, G4TV, Style Network, Current TV, TV Guide Channel, DirecTV, Disney, Nickelodeon, CBS Sports Network, Time Warner Sports, The Golf Channel, Fox Sports Net, Vin DiBona Productions, Freemantle North America and Home & Garden Television.

Chris continues to write/produce/direct and edit his own projects through his company, 'Keyframe Entertainment [us]' .