Dean Winters

Dean Gerard Winters was born on July 20, 1964, in New York City and raised on Long Island. He spent his teenage years in Scottsdale, Arizona, graduating from Brophy College Preparatory in 1982 and Colorado College in 1986. Winters began his acting career relatively later, attending an acting class at age 27. His early television work included a recurring role on NBC’s ‘Homicide: Life on the Street’ before he gained significant recognition.

His career breakthrough came in 1997 with his role as Ryan O’Reily on the HBO prison drama ‘Oz,’ a character known for his manipulative yet compelling nature. Winters’ performance on ‘Oz’ was consistently strong, and the character played integral parts in many of the series’ storylines. He further diversified his portfolio with roles in various television series such as ‘Millennium,’ ‘Rescue Me,’ ’30 Rock,’ ‘Sex and the City,’ and ‘Law & Order: Special Victims Unit’ as Detective Brian Cassidy. He reprised his role as Detective Brian Cassidy in ‘Law & Order: Special Victims Unit’ more than ten years after his initial appearances, becoming a recurring character in later seasons and a love interest for Captain Olivia Benson.

Winters has also appeared in films such as ‘P.S. I Love You’ (2007) and ‘John Wick’ (2014), where he played Avi. A significant turning point in his career came in 2010 when he was cast as ‘Mayhem,’ a recurring character in a television and radio advertising campaign for Allstate Insurance. This role brought him widespread recognition and demonstrated his comedic range. His recent work includes roles in the Netflix film ‘The Out-Laws’ (2023) and the AMC series ‘Monsieur Spade’ (2024), along with recurring roles in ‘Brooklyn Nine-Nine’ as ‘The Vulture’ and ‘Divorce’ as a divorce attorney.