Winter played the role of Rex Brady on the daytime soap opera "Days of Our Lives" from July 8, 2002 until July 26, 2005. After leaving "Days of our Lives", he had many small roles in television shows, such as "", "Love, Inc.", "Charmed", and "Just Legal." He guest-starred on ABC Family's "Wildfire" for five episodes. His character, R.J. Blake, a bull-rider who dated the character of Dani Davis (played by Nicole Tubiola), was killed in the episode "Heartless" which aired originally on February 28, 2007. Winter also appeared on "The Parkers" in the episode "The Boomerang Effect". Winter appeared in an episode of the CBS series "The Ex-List", and a recurring role of Jason McCallister, the brother of Senator Robert McCallister (Rob Lowe) and love interest of Kevin Walker (Matthew Rhys) on the ABC drama "Brothers & Sisters". He was a regular on the short-lived CBS series "Viva Laughlin" and "Moonlight". Winter appears in the feature films "Harold & Kumar Escape from Guantanamo Bay" (2008) and "The Ugly Truth" (2009).