Dean Winters

Dean Winters

61 · Born: Jul 20, 1964

Personal Details

Official Socials
BornJul 20, 1964 New York City, New York, USA
Relatives
  • Scott William Winters (Sibling)
  • Bradford Winters (Sibling)
  • Blair Winters (Sibling)
  • Hudson Dean Zamacona (Niece or Nephew)

Biography

Dean Winters is a talented actor, renowned for his versatility and impressive range. His breakthrough role was as Ryan O'Reily on HBO's critically-acclaimed series Oz, which earned him widespread recognition. He subsequently made a memorable appearance as Tina Fey's character's "Beeper King" boyfriend on the Emmy-winning comedy, 30 Rock.

Winters's outstanding comedic performance in 30 Rock was included in Entertainment Weekly's "Must List" and Variety's short-list of Emmy-worthy guest performances. In addition to his work in television, he has appeared in several films, including P.S. I Love You, alongside Hilary Swank.

On the small screen, Winters was a series regular on FX's critically-acclaimed drama Rescue Me, playing the role of Johnny Gavin, an NYPD police detective, and brother to Denis Leary's character. He also recurred as Lena Headey's former love interest on the Fox series, Terminator: The Sarah Connor Chronicles.

Winters has also had notable roles in various other television shows, including Law & Order: Special Victims Unit, where he played Detective Brian Cassidy, and CSI: Miami, Sex and the City, Third Watch, The Twilight Zone, Millennium, New York Undercover, NYPD Blue, and Homicide: Life on the Street.

In addition to his television work, Winters has appeared in a range of films, including Winter of Frozen Dreams, Bristol Boys, Hellraiser: Hellseeker, Bullet in the Brain, Snipes, Undercover Angel, All Shook Up, Conspiracy Theory, starring Mel Gibson and Julia Roberts, Firehouse, Sidney Lumet's television movie Strip Search, and The Devil You Know.

Furthermore, Winters has become synonymous with his role as the Allstate spokesmodel character known as Mayhem, and has continued to impress audiences with his diverse range of performances throughout his career.

Career

2025
Highest 2 Lowest
Highest 2 Lowest as Det. Higgins
ZO
ZO as Ryan O'Reily
Monsieur Spade
Monsieur Spade as Father Morgan
2023
The Out-Laws
The Out-Laws as Vince Millen
2022
Joe vs. Carole
Joe vs. Carole as Jeff Lowe
2021
DC Showcase: The Losers
DC Showcase: The Losers as Capt. Storm (voice)
Palmer
Palmer as Jerry
2020
Lost Girls
Lost Girls as Dean Bostick
2019
Framing John DeLorean
Framing John DeLorean as John Valestra
Wayne
Wayne as Bobby
2018
2017
Rough Night
Rough Night as Detective Frazier
Divorce
Divorce as Tony Silvercreek
2015
Battle Creek
Battle Creek as Detective Russ Agnew
2014
Don Peyote
Don Peyote as Gun Dealer
2013
2009
2006
Rescue Me
Rescue Me as Johnny Gavin
2005
2004
Strip Search
Strip Search as Ned McGrath
2002
Hellraiser: Hellseeker
Hellraiser: Hellseeker as Trevor Gooden
2001
Snipes
Snipes as Bobby Starr
Bullet in the Brain
Bullet in the Brain as Bank Robber
1999
Undercover Angel
Undercover Angel as Harrison Tyler
1997
Firehouse
Firehouse as Nick Wilkinson
Lifebreath
Lifebreath as Chrystie's Lover
Oz
Oz as Ryan O'Reily