- Spent six years traveling around the world after graduating college.
- Was a New York City bartender before landing his first acting role.
- Joined the Workhouse Theatre Company while studying with Will Esper.
- Nearly died from a bacterial infection in 2009; he spent three weeks in the ICU and had to have two toes and half a thumb amputated.
- In 2010, began playing Mayhem in a long-running series of Allstate Insurance ads.
- Blair Winters — Sister
- Scott William Winters — Brother
- Brad Winters — Brother
- Colorado College, Colorado Springs, Colorado, United States