He is known for his role as Ryan O'Reily on the HBO prison drama Oz and his roles in the TV series Millennium, Rescue Me, 30 Rock, Sex and the City, and Law & Order: Special Victims Unit, as well as portraying "Mayhem" in a series of Allstate Insurance commercials.

He has also made guest appearances on Homicide: Life on the Street, Third Watch, NYPD Blue, CSI: Miami and as Dennis Duffy in 30 Rock as well as previously having an accompanying role in Rescue Me.

He starred in the 1999 romantic comedy Undercover Angel with Yasmine Bleeth and the 2002 direct-to-video horror film Hellraiser: Hellseeker.

Winters played Detective Sam Tyler's father in the US version of Life on Mars.

An HBO comedy special led him to the role he portrayed on Oz, the HBO-produced prison drama.

Winters co-starred in one season of the CBS cop drama series Battle Creek, playing a small-town police force detective opposite Josh Duhamel, the FBI resident agent assigned to the town.

He underwent multiple surgeries and developed gangrene, resulting in the amputation of two of his toes and half of one of his thumbs.