Dean Winters
Biography
Dean Winters is an American actor who was born in New York City and raised on Long Island. He got his first credited screen role on Homicide: Life on the Street after meeting its creator, Tom Fontana, while tending bar, and Fontana went on to write the part of Ryan O'Reily for him on the prison drama Oz, a role he played across 56 episodes from 1997 to 2003. He was a regular on the first season of Law & Order: Special Victims Unit as Detective Brian Cassidy, a character he returned to years later, and had recurring roles as Johnny Gavin on Rescue Me and Dennis Duffy on 30 Rock. On film he played Avi in John Wick (2014), Tom in P.S. I Love You (2007), and appeared in Hellraiser: Hellseeker (2002), Framing John DeLorean (2019) and The Out-Laws (2023). He also played Mayhem in Allstate commercials.
62years old
Turns 63 on July 20in 280 days
- Born New York City
- Star sign: CancerThe sign runs June 21 to July 22
- Also credited as Dean Gerard Winters
Movie Career
- Films
- 15
- Career span
- 23 years2002 to 2025
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Big break
Winters met Tom Fontana, the creator of Homicide: Life on the Street, while tending bar, and agreed to a three-episode arc. Fontana then created the role of Ryan O'Reily for Oz with Winters in mind.
A role that slipped away
Winters was cast in Happy Town, an ABC drama pilot made by the creators of October Road, but Steven Weber replaced him after the pilot was shot.
Big break
Tina Fey brought Winters back to acting in 2010, when he returned to 30 Rock after time away from the profession.
Dean Winters movies on Netflix
Highest 2 Lowestas Det. Higgins
The Out-Lawsas Vince Millen
Christmas vs. The Waltersas Brian Walters
Palmeras Jerry
Lost Girlsas Dean Bostick
Framing John DeLoreanas John Valestra
After Everythingas Blake
Rough Nightas Detective Frazier
Don Peyoteas Gun Dealer
John Wickas Avi
Today's Specialas Steve
Winter of Frozen Dreamsas Ken Curtis
P.S. I Love Youas Tom
Strip Searchas Ned McGrath
Hellraiser: Hellseekeras Trevor Gooden
Best known for
The films on Netflix they are best known for, with the part played in each.
Worked with
Dean Winters shares two films with Kevin Corrigan, and one with each of the others. Pick a number on the chart or a name in the list to see the films they share.









Films together
Kevin Corrigan2 films together, 2009 to 2020
Kevin Corrigan's page Lost Girls2020IMDb rating 6.2Winters as Dean BostickCorrigan as Joe Scalise
Today's Special2009IMDb rating 6.6Winters as SteveCorrigan as Stanton
Gina Gershon2 films together, 2007 to 2018
Gina Gershon's page After Everything2018IMDb rating 6.5Winters as BlakeGershon as Tracy
P.S. I Love You2007IMDb rating 7.0Winters as TomGershon as Sharon
Willem Dafoe1 film together, 2014
Willem Dafoe's page John Wick2014IMDb rating 7.5Winters as AviDafoe as Marcus
Alec Baldwin1 film together, 2019
Alec Baldwin's page Framing John DeLorean2019IMDb rating 6.5Winters as John ValestraBaldwin as John DeLorean
Bruce Dern1 film together, 2021
Bruce Dern's page Christmas vs. The Walters2021IMDb rating 4.5Winters as Brian WaltersDern as Cliff Walters
John Leguizamo1 film together, 2014
John Leguizamo's page John Wick2014IMDb rating 7.5Winters as AviLeguizamo as Aurelio
Chad StahelskiDirector, 1 film, 2014
All films by Chad Stahelski John Wick2014IMDb rating 7.5Winters as Avi
David LeitchDirector, 1 film, 2014
All films by David Leitch John Wick2014IMDb rating 7.5Winters as Avi
Richard LaGraveneseDirector, 1 film, 2007
All films by Richard LaGravenese P.S. I Love You2007IMDb rating 7.0Winters as Tom
Box office
What Dean Winters's films earned in cinemas worldwide.
Combined worldwide box office
$292 million
5 of the 15 films have a worldwide figure.
Of the 15 films: 5 worldwide figure; 3 us gross only; 4 never in cinemas; 3 figure not found.
- 5Worldwide figure
- 3US gross only
- 4Never in cinemas
- 3Figure not found
Top grosser

Highest grossing
The five biggest films earned 100% of the total. The bars are drawn to scale.
- 1$157M53.7% of the total
- 2$86M29.5% of the total
- 3$47M16.2% of the total
- 4$1.5M0.5% of the total
- 5$401K0.1% of the total










