Dean Winters

About

Actor who has played supporting roles for shows like 30 Rock and Rescue Me and stars as "Mayhem" in Allstate Insurance commercials. One of his most iconic roles is playing Ryan O'Reily on the HBO series Oz.

Before Fame

He had a late start in his acting career, enrolling in acting classes at age 27 and working as a bartender to support himself. He worked as a bartender before breaking into acting.

Trivia

He also made appearances on Law & Order, NYPD Blue, and CSI: Miami.

Family Life

He is the eldest child and has three siblings who are named Bradford, Blair and Scott.

Associated With

He played Dennis Duffy on 30 Rock, starring Tina Fey. He attended the same middle school as Matt Dillon and Kevin Dillon did. He and Rita Moreno are friends.