• Dean Winters is an American award-winning actor best known for his roles as Ryan O’Reilly in “Oz” and Dennis Duffy in “30 Rock”
• He is of Irish and Italian ancestry and is fluent in Italian
• His career began with roles in “Homicide: Life on the Street”, “Oz”, “Conspiracy Theory”, and “Undercover Angel”
• He found success with roles in “30 Rock”, “Brooklyn Nine-Nine”, “John Wick”, “Divorce”, and more
• He has a net worth of $6 million and is known for his role as Mayhem in Allstate Insurance Commercials

Who is Dean Winters?

Dean Winters is an American award-winning actor, perhaps still best known to the world as Ryan O’Reilly in the TV series “Oz” (1997-2003), and as Dennis Duffy in the TV series “30 Rock” (2006-2012), among several other notable roles that he has secured so far in his acting career.

Dean Winters Biography: Age, Childhood, and Education

Dean Gerard Winters was born on 20 July 1964 under the Cancer zodiac sign, in New York City, USA, to Patrick Winters and his wife Magna. He spent his childhood on Long Island with his two brothers, Scott and Bradford, and sister Blair. Of Irish and Italian ancestry, Dean is fluent in the Italian language.

He lived in Scottsdale, Arizona during his teenage years where he attended Chaparral High School. After matriculation, he became a student of Brophy College Preparatory, a Jesuit school located in Phoenix. Later, he enrolled at Colorado College, but also spent a summer at the Royal Academy of Dramatic Art (RADA) in London, England. His education didn’t end there, as he studied art history in London, and studied Italian in Florence, Italy.

Career Beginnings

Dean struggled to launch his acting career, and worked in bars and clubs around Manhattan with his brother Scott William Winters, who is now also an actor. However, it was during these bar stints that he met Tom Fontana, Primetime Emmy Award-winning writer, and a producer.

Fontana then wrote the character Tom Marans just for Dean in his TV series “Homicide: Life on the Street” – from 1995 to 1996, Dean appeared in three episodes of one of the most popular crime-drama series. In 1997, Fontana cast him again in his own creation, this time in the TV crime-drama series “Oz”, in which he co-starred alongside Ernie Hudson, J.K. Simmons, and Lee Tergesen, portraying Ryan O’Reilly in all 56 episodes of the Primetime Emmy Award-nominated series.

During his stint on “Oz”, Dean was building his portfolio by appearing in several other projects. For instance, he featured in the action mystery-thriller film “Conspiracy Theory” (1997), starring Mel Gibson, Julia Roberts, and Patrick Stewart, and co-starred in the comedy-drama film “Undercover Angel” (1999) with Yasmine Bleeth and Emily Mae Young.

Before the decade ended, Dean was selected for the part of Brian Cassidy in the TV crime-drama series “Law & Order: Special Victims Unit”, and was a recurring member up until 2019, appearing in 31 episodes of the eponymous crime-drama.

In 2002 he was the main star of the “Hellraiser” franchise film entitled “Hellraiser: Hellseeker”, and in 2004 appeared in films “Brooklyn Bound” and “Love Rome”.

Rise to Prominence

In 2006 he was cast in his first major role after “Oz”, and for that he credits Rita Moreno. She took him under her wing and helped the struggling actor, not only his mentor but also his best friend.

He was then selected for the part of Dennis Duffy in the TV comedy series “30 Rock”, sharing the screen with Tina Frey, Alec Baldwin and Tracy Morgan, while appearing in 15 episodes between 2006 and 2012, but it was enough to boost his career.

In 2008, he joined Lena Headey as her love interest in the fantasy action-drama series “Terminator: The Sarah Connor Chronicles”, and then in 2009 appeared in the comedy film “Spliterheads”, written and directed by Brant Sersen.

His next prominent role was as Detective ‘The Vulture’ Pembroke in the TV crime-drama series “Brooklyn Nine-Nine” (2013-2019), and then as Avi in the action crime-thriller film “John Wick”, with Keanu Reeves, Michael Nyquist and Alfie Allen in the lead roles, while in 2015 he portrayed Russ Agnew in the short-lived comedy crime-drama series “Battle Creek”, starring next to Josh Duhamel and Aubrey Dollar.

Dean Winters

Dean continued his rise to prominence, first as Detective Frazier in the comedy crime-thriller film “Rough Night”, with Scarlett Johansson, Kate McKinnon and Zoe Kravitz in the lead roles, and then as Tony Silvercreek in the TV comedy-drama series “Divorce”, with Sarah Jessica Parker, Thomas Haden Church, and Molly Shannon in the lead roles. He played Blake in the romantic comedy-drama film “After Everything” (2018), starring Marisa Tomei, Sendhil Ramamurthy and Gina Gershon, and in 2019 he was Bobby Luccetti in six episodes of the short-lived action-comedy series “Wayne”.

He guest-starred in the TV series’ “American Gods” and “City on a Hill”, both in 2019, while most recently he portrayed Jerry in the drama film “Palmer”, with Justin Timberlake, Juno Temple and Alisha Wainwright as the main stars of the film. He joined the cast of the Primetime Emmy Award-nominated new series “Girls5eva”, which includes the popular singer Sarah Bareilles, Busy Philipps and Paula Pell, and is currently working on several projects, including the film Street Justice”, which is now in pre-production. Furthermore, he is set to star as Brian Walters in the comedy film “Christmas vs. The Walters”, set for release late in 2021.

Personal Life, Dating, Single, Health Problems

When it comes to his personal life, Dean has been seen with a few celebrities by his side. Back in the ‘90s, he was in a relationship with actress Jennifer Esposito, but their romance didn’t last very long. His next romance was with Maggie Maggie Marigliano in 2002, but apparently that was also a short fling. Since then, he has been silent or secretive about his love life.

Dean has had several major health issues; in 2009 he contracted a pathogenic bacteria and went into cardiac arrest before being transported to the nearest hospital by ambulance – he was clinically dead for three and a half minutes before the paramedics were able to revive him. As a result, Dean spent three weeks in intensive care.

His health problems didn’t end there, as he developed gangrene and had to have two toes amputated and half of one thumb. He subsequently underwent a skin graft operations to repair the damaged tissue, so was on a break from acting for a year between 2009 and 2010.

Net Worth

As of mid- 2021, Dean Winters’ net worth has been estimated to be around $6 million, earned through his successful career as an actor, during which he has appeared in more than 65 film and TV titles, all of which have added to his wealth.

Appearance and Vital Statistics

This award-winning actor has dark brown hair and brown eyes. He stands at a height of 6ft 2ins (1.87m), while he weighs approximately 175lbs (79kgs).

His vital statistics are currently unknown, but he has a fit figure.

Hobbies and Trivia

Dean is also known as the character named Mayhem in the Allstate Insurance Commercials, so far featuring in more than 110 ads, which has also helped his career.

Dean loves spending time with his family and friends. He has remained close friends with Rita Moreno, and is also close with Tina Frey, as she joined him in the Mayhem commercials.

Dean has said that he avoids gyms, but remains fit by walking everywhere around New York City.

He’s also known as one of the founding actors in the Workhouse Theater in Tribeca.


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