By the age of nine, Wylie was busy with voice-over work, including the voice of young Prince Derek in The Swan Princess (1994),[3] and David in All Dogs Go to Heaven 2 (1996).

as Curly (1996–2002), Crayola Kids Adventures, Napoleon as the title character (1997), The King and I (1999) as Louis Leonowens, and Walt Disney Television Animation's pilot Kitty's Dish (as Josh).

Wylie's voice credits also include Batman Beyond, Pepper Ann as Crash, As Told By Ginger as Ian Richton, Midnight Club II, Jimmy Olsen in the 2007 direct-to-DVD film, Superman: Doomsday, the roles of Fred Nerk, Nigel Thrall and Bananas B on American Dragon: Jake Long, Avatar: The Last Airbender, Ben 10, and the character Justin in The Easter StoryKeepers.

This was followed by appearances in many other television programs, including as a series regular in Love and Marriage as Max, Ed as David Mirsky (2001), and Gilmore Girls as Brad Langford (2001–2003), he played Garfield in The Biggest Fan (2002) and as a guest star in 7th Heaven as Marvin, Sliders as Trevor, Touched by an Angel as Andy Erskine, Judging Amy as Nicholas Binkow, MTV Undressed as Owen, Entourage, Living Single, Monk, CSI: Miami, and Veronica Mars.

Wylie was cast as Garfield (Debbie Warden's older brother) in the Dream Street film The Biggest Fan.

Wylie's first motion picture appearance was in Child's Play 2 (1990), which was followed by roles in films including Kindergarten Cop as Larry (1990), Santa With Muscles (1996), Children of the Corn V: Fields of Terror as Ezekial (1998), Breaking Free as Billy (1995), Cutaway as Cal (2000), Can of Worms as Nick (1999), Flying Virus as Adam (2001), Daybreak as Newton Warner (2001), Rebound (2005), and American Pie Presents: Band Camp as Guy (2005).

He has also appeared frequently in regional theatre, including in Camelot as Merlyn-Tom-Morgan at the North Shore Music Theatre (Massachusetts) in 2005,[5] Big River as Huck Finn, 110 in the Shade as Jimmy Curry in 2004 at the Pasadena Playhouse (California),[6] On the Town as Chip in 2003 at the Gateway Playhouse, Bellport, New York,[7] Footloose as Willard, Precious Sons as Freddie Jr., House Arrest as Todd, and Beauty and the Beast, as Chip.