Dean Winters is a famous television actor that is most known for his character, Ryan O’Reily on the HBO prison drama, OZ. He is also recognized a lot for playing Mayhem in a series of Allstate Insurance commercials.


Dean Winters was born on July 20, 1964 in New York City, New York. He was born to American parents, Patrick Winters and Magna Winters. He was one of four children in his family unit. After growing up in Long Island, Winters along with his family moved to Scottsdale, Arizona. Being very skillful at basketball, he played in many games for his high school. He graduated from high school in 1982. He went to college at Colorado College and graduated in 1986. His major in college was theatre which would lay the blueprint for his future career.

Acting Career

Dean got his break in the acting industry through the HBO show Oz. His character, Ryan O’Reily was very much appreciated by the audiences. He starred in all 6 seasons of the popular TV show. After Oz wrapped up, he continued to act in several other TV shows. He was also part of the Law and Order series. He played the role of Detective Brian Cassidy in Law & Order: Special Victims Unit. His character was a regular in the first season. He came back to reprise his role of the detective in the 13th season finale. He also appeared as a recurring character in the 14th and 15th seasons of Law and Order: Special Victims Unit.

In 1999, he acted opposite Yasmine Bleeth in a romantic comedy called “Undercover Angel”. In 2002, he starred in a horror film called Hellraiser: Hellseeker. Winters has appeared in several major motion pictures including Conspiracy Theory (1997), Snipes (2001) and P.S. I Love you (2007).

Dean also made appearances as a guest star in many other TV shows like Third Watch, Sex and the City, Homicide: Life on the Street, and 30 Rock. He played the character Dennis Duffy in the popular comedy TV show 30 Rock. His character appeared in 14 episodes of the show because the producers enjoyed his comedic timing.

Working With The Best in Hollywood

In an interview with Esquire, Dean spoke about the process of working with high profile producers and directors. As he has made his way up the ladder in the entertainment industry, he has been offered better roles with elite crews. Vince Gillian is a highly respected executive producer that is most famous for creating the very successful show, Breaking Bad. He was also one of the main writers for the science fiction classic, X-Files. David Shore is known for creating the medical hit drama, House. When the duo created a new show for CBS called Battle Creek and asked Dean to be on the show because they respected his work.

The crazy thing about the offer from the two major creators was that Dean turned down their offer at first, “In the beginning I did. I said no not because of the material, it's just I've lived in New York my whole life and I'm a city kid, very comfortable here, so it's tough to say yes to something shooting in L.A. I did The Sarah Connor Chronicles years ago but I basically commuted coast to coast for that show.”


The job offer required travel which was a sticking point for Dean but something about the script convinced him to take the offer, “I got the script for Battle Creek around this time last year and I thought it was different and something I hadn't seen which was a buddy-cop show where they aren't buddies. I'd loved Breaking Bad and then knowing David Shore's work and Bryan Singer's The Usual Suspects is one of my all-time favorite films—like you said, you can't say no. “

Since Gilligan made his name on cable, there were initial doubts that his new show could work on a national network like CBS. Dean shared the same worries, “That was my biggest fear. I'm a big fan of storytelling, but I don't like censored stories, so I was very reluctant to jump into that. Not that there aren't great shows on network, but I was nervous. And they are well aware of the competition from cable, but at the end of the day, it's a lofty expectation that a network is going to do what Game of Thrones does. You can't do it. You're selling soap and toothpaste but these guys wanted to bring it to the edge and I feel this is True Detective-light.”

Medical Scare

Winters was contracted with a bacterial infection on June 2009. Because of the infection, he collapsed when he went to meet his doctor. He was immediately taken in an ambulance to the hospital but on the way there, he went into cardiac shock. Though he was unconscious for 2 minutes, he was successfully revived by the paramedics. He was then held in ICU for 3 more weeks. His medical condition did not improve as he was diagnosed with Gangrene which required him to cut off his one thumb and two toes. Ten more operations were required for his body to recover. Due to his medical condition, he was not able to act in TV. He joked in a TV interview that he was one of the few lucky to read his own obituary.

Personal Life

Dean Winters has not yet been married and there is no information available about his relationships. It is speculated that he is living the bachelor life because he is enjoying a recent rise in fame. He has acted for a long time but he didn’t hit it big until recently. He now has a lot of roles lined up which has made him a desired man in his dating circle. He will not have a hard time finding a wife soon.

Net Worth

Dean Winters has a net worth of 4 million dollars that he has made from his acting appearances in films, television, and commercials.

Last Modified: Apr 7, 2020

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