- Directed his first two major-label music videos for RCA Recording artists, The Verve Pipe and Rachael Yamagata before graduating from Northwestern University's Radio/TV/Film program.
- Was a production assistant to Jay Bennett and Jonathon Parker at Wilco during the summer of 2000. With the help of Jonathon Parker, he used Wilco's recording equipment on nights and weekends to track the music to his first short film entitled, Horizon.
- His parents run a nudist club, Sanibel Naturists, located on a private beach on the gulf coast of Florida.
- Was a College Marketing Representative for Sony Music from fall 2000 to 2001. He exited Sony to direct his first music video for The Verve Pipe.
- Sister, Amy Riley-Lucas - is a partner and entertainment and media lawyer at O'Melveny and Myers, LLP.
- At 10 months old, appeared in an ad for children's pony saddles for Western Country Store and at age 7 appeared in Hoosiers (1986) opposite Dennis Hopper's character, Shooter.
- Brother-in-law of CAA talent agent, Rick Lucas.
- Plays drums and percussion in several bands. Originally majoring in Percussion Performance before a car accident involving a 92 yr old man (whom ran a red light while making a left turn fleeing his retirement community) badly injuring Riley'wrist. Started writing the screenplay to his first short film while completing physical therapy and recovering from several Orthopedic surgeries to rebuild his wrist.
- Maternal grandmother was cousins with brilliant, distinguished American director, Budd Boetticher. Both Riley and Boetticher attended the Culver Military Academy in Indiana. Both managed to execute a successful escape from the prison-like dormitory.
- Directly related to American writer, poet, and best-selling author James Whitcomb Riley whom wrote a poem in 1885 entitled, "Little Orphant Annie" that would become the basis for a long-running comic strip, a Broadway play and several successful feature films, Sirotka Enni (1986).
- Contracted the most deadly strain of E. Coli bacteria during Hurricane Sandy in early November 2012 while traveling from a screening of his film, Act Naturally in Soho, New York to Providence, RI at Brown University.
- Is an avid motorcycle and classic mustang enthusiast. Has a collection of classic mustangs, vintage 2-stroke dirt bikes and V-Twin cruisers. He often uses his personal vehicles as picture cars in his Music Videos and Films.
- Has personally screened his debut feature film, Act Naturally at over 100 clothing optional screenings held in art-house theaters and nudist resorts all over the globe.
- Is related to the 13th president of The United States, James K. Polk on his maternal grandmother's side.
- A recovering alcoholic, Riley has been sober since Sept 23rd, 2006. Active in Los Angeles Alcoholics Anonymous and Narcotics Anonymous programs and meetings.
- Plays drums, percussion, backing vocals and something guitar and electric ukulele with his Los Angeles, indie-rock band, Nak'd Lion. His co-producer, Deva Kox plays bass, one of the actors from several film collaborations, Carter James is the band's front man, and Art Director Mike Orth plays lead guitars.
- Built and owns the 3rd legally permitted Shipping Container Home in Los Angeles County.
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