Dean Winters
Known for
An American actor with a gift for wry, hard-edged comic and dramatic roles. He gained a following as the doomed Ryan O'Reily on 'Oz' and Dennis, Liz Lemon's on-again beau, on '30 Rock', and reached wide fame as the accident-prone Mayhem in a long-running insurance ad campaign. On film he played the concierge Charon's colleague and other tough-guy parts, appearing in 'John Wick' (2014) and 'Palmer' (2021). With a gravelly voice and sardonic edge, he is an American character actor equally adept at menace and deadpan comedy.
Dean Winters
29 Movies
31 Series
An American actor with a gift for wry, hard-edged comic and dramatic roles. He gained a following as the doomed Ryan O'Reily on 'Oz' and Dennis, Liz Lemon's on-again beau, on '30 Rock', and reached wide fame as the accident-prone Mayhem in a long-running insurance ad campaign. On film he played the concierge Charon's colleague and other tough-guy parts, appearing in 'John Wick' (2014) and 'Palmer' (2021). With a gravelly voice and sardonic edge, he is an American character actor equally adept at menace and deadpan comedy.
Movies
Plays Cleet
Conspiracy Theory
1997
Plays Avi
John Wick
2014
Plays Bartender
Teenage Mutant Ninja Turtles: Out of the Shadows
2016
Plays Det. Higgins
Highest 2 Lowest
2025
Plays Detective Frazier
Rough Night
2017
Plays Tom
P.S. I Love You
2007
Plays Mikey
Eenie Meanie
2025
Plays Jerry
Palmer
2021
Plays Vince Millen
The Out-Laws
2023
Plays Captain Storm (voice)
Justice League: Crisis on Infinite Earths Part Three
2024
Plays Trevor Gooden
Hellraiser: Hellseeker
2002
Plays Reggie
Splinterheads
2009
Plays Harrison Tyler
Undercover Angel
1999
Plays Dean Bostick
Lost Girls
2020
Plays Geoff
Father of the Year
2018
Producer
Plays Ryan O'Reily
Zo
2024
Plays Ned McGrath
Strip Search
2004
Plays Jake Kelly
The Devil You Know
2013
Plays Danny
Brooklyn Bound
2005
Plays Blake
After Everything
2018
Plays Capt. Storm (voice)
DC Showcase: The Losers
2021
Plays Gun Dealer
Don Peyote
2014
Plays Brian Walters
Christmas vs The Walters
2021
Plays Ken Curtis
Winter of Frozen Dreams
2009
Plays Bank Robber
Bullet in the Brain
2001
Plays Randy
Bristol Boys
2005
Plays Bobby Starr
Snipes
2001
TV Shows
Plays Ryan O'Reily
Oz
1997
Plays Johnny Gavin
Rescue Me
2004
Plays Brian Cassidy
Law & Order: Special Victims Unit
1999
Plays Dennis Duffy
30 Rock
2006
Plays Detective Russ Agnew
Battle Creek
2015
Plays Bobby
Wayne
2019
Plays Charley Dixon
Terminator: The Sarah Connor Chronicles
2008
Plays Keith 'The Vulture' Pembroke
Brooklyn Nine-Nine
2013
Plays Tony Silvercreek
Divorce
2016
Plays Nick
Girls5eva
2021
Plays Jeff Lowe
Joe vs Carole
2022
Plays Vic Tyler
Life on Mars
2008
Plays Tom Marans
Homicide: Life on the Street
1993
Plays Father Morgan
Monsieur Spade
2024
Plays Andrew (voice)
Rapunzel's Tangled Adventure
2017
Plays Mr. Crocell
Millennium
1996
Plays Dick Frank
So Help Me Todd
2022
Plays Des Lonegan
Deadline
2000
Plays "FDNY: Chicago" Star
The Fall and Rise of Reggie Dinkins
2026
Plays Gordon
The Twilight Zone
2002
Plays Birdman
Berlin Station
2016
Plays Bill Stram
Third Watch
1999
Plays Raymond Caine
CSI: Miami
2002
Plays John McFadden
Sex and the City
1998
Plays Casey Brinkley
Up All Night
2011
Plays (voice)
American Dad!
2005
Plays Bunny (voice)
Unbreakable Kimmy Schmidt
2015
Plays Mike Stoat
Law & Order: Criminal Intent
2001
Plays Larry
NYPD Blue
1993
Plays Paul Delaney
New York Undercover
1994
Latest Trailers
Watch Trailer
Eenie Meanie
Full Filmography
The Fall and Rise of Reggie Dinkins
"FDNY: Chicago" Star · 1 episode
2026–
TV
Eenie Meanie
Mikey
2025
Film
Highest 2 Lowest
Det. Higgins
2025
Film
Justice League: Crisis on Infinite Earths Part Three
Captain Storm (voice)
2024
Film
Zo
Ryan O'Reily
2024
Film
Monsieur Spade
Father Morgan · 2 episodes
2024–
TV
The Out-Laws
Vince Millen
2023
Film
So Help Me Todd
Dick Frank · 2 episodes
2022–
TV
Joe vs Carole
Jeff Lowe · 3 episodes
2022–
TV
Photos
Frequently Asked Questions
How old is Dean Winters and where are they from?
Dean Winters is 62 years old, born on July 20, 1964 in New York City, New York, USA.
What are the most famous roles of Dean Winters?
Dean Winters is best known for roles in John Wick, Teenage Mutant Ninja Turtles: Out of the Shadows, P.S. I Love You.
How many movies has Dean Winters been in?
Over a 30-year career (since 1996), Dean Winters has appeared in 29 movies and 31 TV shows.
What was Dean Winters's first movie?
The career of Dean Winters began with Firehouse (1996).
What is Dean Winters's most recent movie or series?
Dean Winters's most recent release is The Fall and Rise of Reggie Dinkins, which premiered on January 18, 2026.
What TV shows has Dean Winters appeared in?
On television, Dean Winters has appeared in Law & Order: Special Victims Unit, Brooklyn Nine-Nine, American Dad!, Sex and the City.
Dean Winters
1964-07-20 · New York City, New York, USA
Dean Winters (born July 20, 1964) is an American actor, who is known for his roles as Bobby on the YouTube series Wayne, Detective Brian Cassidy on Law & Order: SVU, Detective Russ Agnew on Battle Creek, 'The Vulture' Detective Pembroke on Brooklyn Nine-Nine, Charley Dixon on FOX's Terminator: The Sarah Connor Chronicles, Dennis Duffy on NBC's 30 Rock, Johnny Gavin on FX's Rescue Me, Ryan O'Reily on HBO's Oz. He also portrays "Mayhem" in Allstate commercials.