[2][5] He graduated from Alburnett Junior-Senior High School in 1997, and his original intention was to earn a college degree to complement his Equine interests,[2][3] but he was "discovered" at the Westdale Mall in Cedar Rapids by a local talent scout[6] and flew to New York City to compete at the International Modeling and Talent Association (IMTA) Convention.
[12] For the film New York Minute, he and co-star Jared Padalecki were hand-picked for their roles by stars Mary-Kate and Ashley Olsen.
[6] For their work in the film, key production members were awarded a 2005 CAMIE Award; These included executive producer Todd Garner, director Michael Tollin, screenwriter Mike Rich, and actors Cuba Gooding Jr., Ed Harris, Riley Smith, Alfre Woodard, Brent Sexton, S. Epatha Merkerson and Sarah Drew.
[14] He played Russ, the love interest of Mary Elizabeth Winstead's character in the dancing film Make It Happen.
Smith took up the guitar to fill downtime while on film sets, and in 2006, he and Henri O'Connor formed the band "The Life of Riley", of which he is guitarist and lead singer.
[12] As of August 2010, the Los Angeles–based group has released three CDs: The Life of Riley (2007), Long Way Home EP (2009) and Live in Hollywood at the Hotel Cafe (2010).