Dean Winters: The Resilient Journey of an Award-Winning Actor

Dean Winters is an American award-winning actor best known for playing Ryan O’Reilly in “Oz” (1997-2003) and Dennis Duffy in “30 Rock” (2006-2012), among other significant roles.

Dean Winters’ Net Worth?

Film and television star Dean Winters has a $6 million net worth. He was known for playing Ryan O’Reily in “Oz” (1997–2003), Johnny Gavin in “Rescue Me” (2004–2011), and Dennis Duffy in “30 Rock” (2006–2012). Winters has portrayed Mayhem in Allstate advertising since 2010. He has appeared in “P.S. I Love You” (2007), “John Wick” (2014), “Lost Girls” (2020), and “Law & Order: Special Victims Unit” (1999-2019), “Terminator: The Sarah Connor Chronicles” (2008-2009), “Brooklyn Nine-Nine” (2013-2019), and “Battle Creek” (2015).

Dean Winters produced, starred, and acted in the 2018 Award-winning short film “A Civilised Life.” His work in movies and television has strengthened his position.

Profile of Dean Winters Full name Dean Gerard Winters Dean Winters Gender Male Birthday: July 20, 1964 Age: 58 in 2023 Astrological sign Cancer Birthplace New York City, USA Current residence Tribeca, NY Nationality American Ethnicity Irish-Italian mixed race Religion Christianity Sexuality Straight Six-foot-two-inch height 187 pounds 174 kilogrammes 79 Hair colour Dark brown Eye colour Light brown Three siblings (Scott, Bradford, and Blair Winters) Former partner Maggie Marzigliano (2002) Chaparral High School Brophy College Preparatory and Colorado College Profession American actor, stuntman, producer Net value $6m 

Dean Winters Biography

Dean Gerard Winters was born in New York City to Patrick and Magna Winters on July 20, 1964, under the Cancer zodiac sign. He grew up on Long Island with brothers Scott and Bradford and sister Blair. Dean, of Irish and Italian descent, speaks Italian.

Scottsdale was his teenage home, where he attended Chaparral High School. His Jesuit school was Brophy College Preparatory in Phoenix after matriculation. He later attended Colorado College and spent a summer at RADA in London. He also studied art history in London and Italian in Florence.

Career Beginnings

Dean struggled to start his acting career and worked in Manhattan pubs and clubs with his brother Scott William Winters, who is also an actor. These pub appearances introduced him to Primetime Emmy-winning writer and producer Tom Fontana.

Fontana penned Tom Marans for Dean in his 1995–1996 TV series “Homicide: Life on the Street,” appearing in three episodes of one of the most successful crime dramas. Fontana cast him again in his own creation, “Oz,” in 1997, co-starring with Ernie Hudson, J.K. Simmons, and Lee Tergesen as Ryan O’Reilly in all 56 episodes of the Primetime Emmy Award-nominated criminal thriller.

Dean expanded his portfolio by appearing in various productions while on “Oz”. He appeared in the action mystery-thriller “Conspiracy Theory” (1997) with Mel Gibson, Julia Roberts, and Patrick Stewart, and in the comedy-drama “Undercover Angel” (1999) with Yasmine Bleeth and Emily Mae Young.

Dean was cast as Brian Cassidy on “Law & Order: Special Victims Unit” before the decade ended and appeared in 31 episodes till 2019.

In 2002, he starred in “Hellraiser: Hellseeker” and in 2004, in “Brooklyn Bound” and “Love Rome”.

Rise to Prominence

Rita Moreno helped him land his first major job following “Oz” in 2006. She became his mentor and dearest friend, helping the struggling performer.

He then played Dennis Duffy in 15 episodes of “30 Rock” with Tina Frey, Alec Baldwin, and Tracy Morgan from 2006 to 2012, which boosted his reputation.

Dean Gerard appears in Brant Sersen’s 2009 comedy “Spliterheads” after playing Lena Headey’s love interest in “Terminator: The Sarah Connor Chronicles” in 2008.

He then played Detective ‘The Vulture’ Pembroke in the TV crime-drama series “Brooklyn Nine-Nine” (2013–2019), Avi in the action crime-thriller film “John Wick” with Keanu Reeves, Michael Nyquist, and Alfie Allen, and Russ Agnew in the short-lived comedy crime-drama series “Battle Creek” with Josh Duhamel and Aubrey Dollar in 2015.

Personal Life

Dean died for about five minutes in a NYC ambulance in June 2009. In “US Weekly,” he said, “A childhood ailment made me septic. I died in an ambulance, but Lenox Hill Hospital’s excellent doctors revived me after four and a half minutes.” Winters fell into cardiac arrest in the ambulance and spent three weeks in the ICU before recovering at home for a month.

He lost two toes and half a thumb to gangrene. Dean revealed he had casts on one foot and both arms and had to be propped up on a seat during the “30 Rock” season finale after 10 gangrene surgeries, including skin grafts.

Awards and Nominations

Winters won Best Narrative Short at the California International Shorts Festival and Best Picture at the Hollywood International Moving Pictures Film Festival for “A Civilised Life” in 2018.

The Flickerfest International Short Film Festival (Best Film), Los Angeles World International Film Festival (Best Short Category Overall), New York City Independent Film Festival (Best Short Film), and Phoenix Film Festival (Best Live Action Short Film) also nominated “A Civilised Life”.

From “30 Rock,” Dean received Online Film & Television Association Award nominations for Best Guest Actor in a Comedy Series (2008) and Gold Derby Award nominations for Comedy Guest Actor (2008) and Comedy Guest Actor of the Decade (2010).

Real Estate

Winters bought a 2,500-square-foot New York City duplex loft for roughly $3.5 million in 2018. The two-story residence has a glass-walled solarium, two bedrooms, 2.5 bathrooms, a skylight, and a corkscrew staircase.

Frequently Asked Questions 

Q. Which Dean Winters roles are notable?

Dean Winters is most known for playing Ryan O’Reilly in “Oz” (1997–2003), Dennis Duffy in “30 Rock” (2006–2012), Johnny Gavin in “Rescue Me” (2004–2011), and Mayhem in Allstate Insurance commercials.

Q. Dean Winters’ work: any awards?

Dean Winters received Best Narrative Short at the California International Shorts Festival and Best Picture at the Hollywood International Moving Pictures Film Festival for “A Civilised Life” (2018).

Q. Dean Winters had what health issues?

Dean Winters went into cardiac arrest in June 2009 and died for about five minutes in a New York City ambulance. He lost two toes and half a thumb to infection and gangrene.

Q. Dean Winters said which TV show helped his career after “Oz”?

Dean Winters attributes his career success to his part as Dennis Duffy in “30 Rock” (2006–2012).


Dean Winters’ rise from New York City’s bars to a $6 million actor shows his resilience and talent. Winters’ memorable parts in “Oz,” “30 Rock,” and Allstate Insurance advertisements are among his many TV, film, and commercial roles. Winters has overcome health issues, including a near-death experience, and won honours for his work on the short film “A Civilised Life.” His story shows his power, versatility, and craft dedication.

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