In 1990, Wiles began to pursue an interest in film-making, working on the set of the film Mr. and Mrs. Bridge, filming on location in Kansas City. Not long after, the Stephen King tele-movie, Sometimes They Come Back, came to town and he worked on the crew as well as appearing in scenes as an extra. After forming some connections while working on these films, Wiles ventured to Los Angeles where he appeared in commercials before landing the lead in an after-school special. In 1994, he had a part in the Bon Jovi music video "Always". 1994 also gave him his first lead role, in the indie movie WindRunner, appearing with Margot Kidder and Russell Means. In 1995, Wiles made the first of 32 appearances in Beverly Hills, 90210 as Colin Robbins, a role which gained him some note in Hollywood. In 1999, Wiles garnered the role of Maurice 'Bosco' Boscorelli in the television drama Third Watch; he appeared in all six seasons of the show from 1999-2005.

Wiles expanded into directing and writing, as well as theatre. In the summer of 2002, he appeared in the Cape Playhouse production of Mass Appeal alongside Malachy McCourt, and in 2003 he was in Imua! Theatre Company's production of Safe which was co-written and directed by fellow Third Watch star Anthony Ruivivar. Upon completion of the final season of Third Watch, Wiles began work on his independent film Lenexa, 1 Mile (2006) which he wrote and also directed. Wiles appeared alongside Geena Davis and Donald Sutherland in the TV series Commander in Chief. He played a soldier in the series Army Wives, appearing in two episodes. He directed, produced and wrote a 2009 movie, Play Dead. He had a small part in the 2007 movie Zodiac. He appeared in 2009's horror thriller remake of The Stepfather. In the summer of 2010, he co-starred in the NBC drama-suspense miniseries, Persons Unknown.

Wiles performed a role as guest-star on Law & Order: SVU on October 20, 2010.

In 2015, Wiles was part of the main cast for the MTV series Scream in the role of Sheriff Clark Hudson.