Silberling began his entertainment industry career before completing his studies. In 1986, he became a Production Assistant for a children's program. He then began to direct television and film. Silberling's 2002 film, Moonlight Mile, is loosely based on his bereavement following the murder of his girlfriend, actress Rebecca Schaeffer, in 1989. In 2006, Silberling's movie 10 Items or Less was the first movie made legally available for download during its theatrical run. This became possible through ClickStar and Silberling's close relationship with its owners Morgan Freeman and Lori McCreary. On March 1, 1999, he started out his own production company Reveal Entertainment, with a first-look development deal at DreamWorks.[4] The first project under Reveal was an attempt to purchase the script The Mystery Dance, for himself to direct in mind, but the idea was later scrapped.[5]
Silberling was approached by Warner Bros. as one of the candidates to direct Harry Potter and the Sorcerer's Stone in 1998. Although he began to enthusiastically plan the film in his mind and was ready to sign on to direct it, Chris Columbus was ultimately chosen as the director.[6] On October 22, 2014, his Reveal Entertainment company signed a deal with CBS Television Studios.[7] He was currently signed with ICM Partners.[8]