Initially, Shiloh acted in the commercial for the First 5 California which was directed by Vadim Perelman. Later, he got an opportunity to play the role in his debuted television series – episode named as Cold Case. After which, it was followed by series of TV soap operas namely Lincoln Heights and Drake & Josh. Consequently, in the year 2007, he was given the opportunity to enter the big screen through the role of Edgar in the movie Interstate. However, he returned back to television series – Jericho in the year 2006 as well as 2007 through the role of Sean Henthorn. However, he became extremely popular with his role as a rink manager in the movie Skateland along with the co-star Ashley Greene.
However, Shiloh was extremely happy to get the role of a romantic lead player along with the co-actress Amanda Seyfried. As a matter of fact, this role made him reach new heights in the Hollywood film industry. Most prominently, he was regarded as the Breakout Stars to watch for in the year 2011 by the NextMovie.com of MTV Networks. His upcoming movies namely Chronically Metropolitan and Edge of Winter in the role of Fenton and Richard respectively which are still in the filming stage since 2016. The other television shows include Three Rivers, Gossip Girl, The Cleaner, and much more.