Last Updated on March 10, 2023
Dean Gerard Winters is an American actor best known for portraying Ryan O’Reily on the HBO prison drama ‘Oz.’
Winters also had major roles on the television series ‘Rescue Me,’ ’30 Rock,’ ‘Law & Order: Special Victims Unit,’ ‘Brooklyn Nine-Nine,’ and ‘Sex and the City’ to mention but a few.
Dean Winters Quick Facts
| Full Name: | Dean Gerard Winters |
| Popular Name: | Dean Winters |
| Nicknames: | N/A |
| Birth Date: | July 20, 1964 |
| Age: | 58 years |
| Parents: | Patrick Winters and Magna Winters |
| Siblings: | Scott William Winters (brother), Bradford Winters (brother) and Blair Winters (sister) |
| Birth Place: | New York City, New York, United States |
| Nationality: | American |
| Ethnicity: | Mixed (Irish and Italian) |
| Religion: | Christianity |
| Education: | Chaparral High School, Brophy College Preparatory, and Colorado College |
| Marital Status: | Married to Kathleen Coen |
| Sexual Orientation: | Straight |
| Children: | 2 daughters – Grace Winters and Faith Winters |
| Net Worth: | USD 6 million |
| Source of Wealth: | Acting, Endorsement Deals, and Other Ventures |
| Height: | 6′ 2″ (1.87 m) |
| Weight: | In kilograms: 79 kg; In pounds: 174 lbs. |
Early Life and Career Information
Early Life
Dean Gerard Winters was born on July 20, 1964, in New York City, New York, United States, to Patrick Winters and Magna Winters. His father was an electrical engineer, whereas his mother was a homemaker.
Winters attended Chaparral High School. He graduated from Brophy College Preparatory, a Jesuit school based in Phoenix, Arizona. He then proceeded to Colorado College and graduated from the institution in 1986.
Film Career
Dean Winters made his film debut portraying Cleet in the 1997 movie ‘Conspiracy Theory.’ The same year, he played Chrystie’s Lover in ‘Lifebreath.’
In 1999, Winters portrayed Harrison Tyler in the blockbuster ‘Undercover Angel.’ Two years later, he had a role in the films ‘Snipes’ and ‘Bullet in the Brain.’ He also appeared in Hellraiser: Hellseeker (2002), Brooklyn Bound (2004), Love Rome (2004), Bristol Boys (2006), and Dead Calling (2006).
Winters’ next major film role was as Tom in the 2007 movie ‘P.S. I love You.’ In 2009, the Hollywood superstar appeared in three notable movies – ‘Winter of Frozen Dreams,’ ‘Splinterheads,’ and ‘Today’s Special.’
Dean Winters played Frank Devine in the 2010 short film ‘Vipers in the Grass.’ He appeared in another short movie titled ‘The Worst’ two years later.
In 2013, Winters had roles in the films ‘The Devil You Know’ and Memoire.’ The following year, he portrayed a gun dealer in ‘Don Peyote’ and Avi in ‘John Wick.’
Below are other noteworthy films that Dean Winters has graced over the years;
• Teenage Mutant Ninja Turtles: Out of the Shadows (2016)
• Rough Night (2017)
• After Everything (2018)
• Father of the Year (2018)
• Framing John DeLorean (2019)
• Lost Girls (2020)
• Palmer (2021)
Television Career
Dean Winters made his television debut in a 1995 episode of ‘Homicide: Life on the Street.’ He had recurring roles as Tom Marans in three episodes of the series until 1996.
Winters subsequently portrayed Larry in a 1996 episode of ‘NYPD Blue.’ The following year, he played Nick Wilkinson in the television movie ‘Firehouse.’
Dean Winters appeared in two episodes of ‘Millennium’ between 1997 and 1999. He eventually landed his breakout television role portraying Ryan O’Reily on the HBO prison drama ‘Oz.’ He starred in 56 episodes of the series from 1997 to 2003.
Winters had several television roles while starring in Oz. They include New York Undercover (1998), Sex and the City (1999), Saturday Night Live (1999), Third Watch (2002), and The Twilight Zone (2002). It’s also during this period that Winters began starring in his biggest television project after Oz – Law & Order: Special Victims Unit. He portrayed Brian Cassidy in 31 episodes of the series from 1999 to 2019.
In 2004, Winters appeared as Ned McGarth in an episode of ‘Strip Search.’ The same year, he began portraying Johnny Gavin in ‘Rescue Me’ and went on to feature in 33 episodes of the series until 2011.
Dean Winters’ next television role was as Raymond Caine in a 2005 episode of ‘CSI: Miami.’ He then landed recurring roles as Dennis Duffy in 15 episodes of 30 Rock (2006 – 2012) and as Charley Dixon in 9 episodes of Terminator: The Sarah Connor Chronicles (2008 – 2009).
The following are other major television shows that Dean Winters has featured in over the years;
• Law & Order: Criminal Intent (2008)
• Life on Mars (2008 – 2009)
• Up All Night (2012)
• Westside (2013; television movie)
• Brooklyn Nine-Nine (2013 – 2019)
• Divorce (2016 – 2018)
• Tangled: The Series (2017 – 2019; as a voice actor)
• Berlin Station (2019)
• Wayne (2019)
• Girls5eva (2021)
Other Ventures
Besides his illustrious acting career, Dean Winters has also dabbled in comedy over the years. Winters has performed stand-up alongside renowned comedians like Chris Rock, Jerry Seinfeld, and Paul Reiser.
Dean Winters’ Net Worth
As of November 1, 2022, Dean Winters had a net worth of $6 million. Winters owes much of his wealth to his successful acting career.
A sizable chunk of his earnings also come from his side ventures, including comedy and endorsements. The ‘Oz’ superstar is well-known for portraying Mayhem in several television and radio commercials by Allstate Insurance.
Lessons from Dean Winters
1. Seize the moment
Dean Winters is renowned for making the most of every acting opportunity that comes his way. That explains why he has landed recurring roles on multiple television series.
2. Be yourself
Winters believes in maintaining a powerful self-image, whether in personal or professional engagements. He once said, ‘The best thing an actor can bring to a role is himself – that’s no secret.’
3. Hard work supersedes everything else
Dean Winters’ zeal is unmistakable. His determination is evident both on-screen and off-screen. It’s another reason the ‘Oz’ star has amassed incredible wealth and fame.
Famous Quotes by Dean Winters
• I never go into a scene – ever, ever, ever – thinking, I have to make myself more empathetic toward the audience. Once you start doing that, you get into really dangerous territory. I think you start to become kind of untrue to the character.
• I wanted to become an actor so I didn’t have to put on a suit and sell insurance.
• I’ve done a few jobs out there for the money, and I find those jobs have come back to haunt me.
• School and I never seemed to walk hand in hand.
• Unfortunately, in the Hollywood way, respect comes in the form of a trophy a lot of the time.
Wrap Up
Dean Winters is an actor with tons of movies and television credits to his name. The Hollywood sensation has amassed a $6 million net worth as at November 1, 2022.
