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Dean Winters

Dean Winters

American actor
Dean Winters
The basics

Quick Facts

Intro American actor
Is Actor Film actor Television actor
From United States of America
Type Film, TV, Stage & Radio
Gender male
Birth 20 July 1964, New York City, New York, USA
Age 56 years
Star sign Cancer
Height: 1.8542 m
William Esper Studio
Colorado College
The details


Dean Winters (born July 20, 1964) is an American actor. He is best known for his role as Ryan O'Reily on the HBO prison drama Oz and has also appeared on such television series as Rescue Me, 30 Rock, and Law & Order: Special Victims Unit, as well as the character "Mayhem" in a series of Allstate Insurance commercials. Winters co-starred with Josh Duhamel in one season of the CBS Network cop drama series Battle Creek. In 2013-19, he had a recurring role as Detective 'The Vulture' Pembroke on the television comedy series Brooklyn Nine-Nine.

Early life

Winters was born in New York City, New York. He has two brothers: actor Scott William Winters and writer Bradford Winters, and a sister: Blair Winters.

He grew up on Long Island and spent his teenage years in Scottsdale, Arizona. He attended the Jesuit Brophy College Preparatory school in Phoenix, graduating in 1982. He graduated from Colorado College.


Winters has appeared in two of the Law & Order television series: Law & Order: Special Victims Unit, where he was a regular in the first season, and as a guest star in the Law & Order: Criminal Intent episode "Purgatory". More than ten years after his final appearance on SVU, he again portrayed Detective Brian Cassidy in the 13th-season finale "Rhodium Nights", became a recurring character in the 14th season and, in the 15th season, also became the love interest of Sergeant Olivia Benson (portrayed by Mariska Hargitay). 

Winters has also made guest appearances on Homicide: Life on the Street, Sex and the City, Third Watch, NYPD Blue, CSI: Miami, and as Dennis Duffy in 30 Rock as well as previously having an accompanying role in Rescue Me.

Winters starred in the 1999 romantic comedy Undercover Angel with Yasmine Bleeth and the 2002 direct-to-video horror film Hellraiser: Hellseeker.

He played Tom in PS, I Love You. In the US version of Life On Mars (2008-2009), he played the father of Detective Sam Tyler (played by Jason O'Mara). He also played Charley Dixon, the love interest of Sarah Connor (played by Lena Headey) in Terminator: The Sarah Connor Chronicles.

Winters was cast in the ABC drama pilot Happy Town, from the creators of October Road, but was replaced by Steven Weber after shooting the pilot.

On June 20, 2010, Winters was introduced as "Mayhem," the recurring character in a new television and radio advertising campaign for Allstate Insurance created by the Leo Burnett agency in Chicago.

Winters co-starred in one season of the CBS Network cop drama series Battle Creek, playing a small-town police force detective opposite Josh Duhamel, the FBI Resident Agent assigned to the town. The series was canceled in May 2015.

In 2013-2019, Winters reprised his role on Brooklyn Nine-Nine as The Vulture. He also had a supporting role as a divorce attorney on the HBO series Divorce.

Most recently, in March 2020, Winters was seen as "Dean Bostick" in Liz Garbus' mystery thriller Lost Girls, starring Amy Ryan and Thomasin McKenzie.

He has also finished filming for Fisher Stevens' drama Palmer, in which he will be seen alongside June SquibbJuno Temple, and Justin Timberlake. The release date is yet to be announced.

His other current projects are Christmas vs. The Walters, Street Justice, and Krystyna Loboda's comedy Rites & Wrongs.

Health issues

In June 2009, Winters contracted a bacterial infection and collapsed upon arrival at his doctor's office. While being transported across Central Park in an ambulance, he went into cardiac arrest for over two minutes. Paramedics were able to revive him, and he was hospitalized in intensive care for three weeks. Over the course of the next year, he developed gangrene, requiring the amputation of two toes and half of one thumb, and ten subsequent operations including a skin graft. Winters was away from acting until 2010 when Tina Fey brought him back to 30 Rock and he started work on the Mayhem campaign.



Year Title Role Notes 
1997 Conspiracy Theory Cleet film debut 
1997 Lifebreath Chrystie's Lover  
1999 Undercover Angel Harrison Tyler  
2001 Snipes Bobby Starr  
2001 Bullet in the Brain Bank Robber Short film 
2002 Hellraiser: Hellseeker Trevor Direct-to-Video 
2004 Brooklyn Bound Danny  
2004 Love Rome Dean  
2006 Bristol Boys Randy  
2006 Dead Calling Nick  
2007 P.S. I Love You Tom  
2009 Winter of Frozen Dreams Ken Curtis  
2009 Splinterheads Reggie  
2009 Today's Special Steve  
2010 Vipers in the Grass Frank Devine Short film 
2012 The Worst Night Short film 
2013 The Devil You Know Jake Kelly  
2013 Memoire Gregor Short film 
2014 Don Peyote Gun Dealer  
2014 John Wick Avi  
2016 Teenage Mutant Ninja Turtles: Out of the Shadows Bartender  
2017 Rough Night Detective Frazier  
2018 After Everything Blake  
2018 Father of the Year Geoff  
2018 A Civilized Life Conway Short film; also Producer 
2019 Framing John DeLorean John Valestra Documentary 
2020 Lost Girls Dean Bostick  
2020 Street Justice Patrick Hannigan Pre-production 


Year Title Role Notes 
1995–1996 Homicide: Life on the Street Tom Marans Television debut
Recurring role; 3 episodes 
1996 NYPD Blue Larry Episode: "Where'd the Van Gogh?" 
1996 The Playroom Unknown Television Short 
1997 Firehouse Nick Wilkinson Television Movie 
1997–1999 Millennium Young Michael Lanyard/Mr. Crocell 2 episodes 
1997–2003 Oz Ryan O'Reily Series regular; 56 episodes 
1998 New York Undercover Paul Delaney Episode: "Rat Trap" 
1999 Sex and the City John McFadden Episode: "The Fuck Buddy" 
1999 Saturday Night Live Ryan O'Reily Uncredited; Episode: "Jerry Seinfeld/David Bowie
1999–2019 Law & Order: Special Victims Unit Brian Cassidy Main role; 13 episodes
recurring role; 19 episodes 
2001 Deadline Des Lonegan Episode: "Shock" 
2002 Third Watch Bill Stram Episode: "The Unforgiven" 
2002 The Twilight Zone Gordon Episode: "Future Trade" 
2004 Strip Search Ned McGarth Television Movie 
2004–2011 Rescue Me Johnny Gavin Main role; 33 episodes 
2005 CSI: Miami Raymond Caine Episode: "10-7" 
2006–2012 30 Rock Dennis Duffy 

Recurring role; 15 episodes

Nominated – Gold Derby award for Best Guest Actor in a Comedy Series
Nominated – Online Film & Television Association award for Best Guest Actor in a Comedy Series

2008 Law & Order: Criminal Intent Mike Stoat Episode: "Purgatory" 
2008–2009 Terminator: The Sarah Connor Chronicles Charley Dixon Recurring role; 9 episodes 
2008–2009 Life on Mars Vic Tyler Recurring role; 3 episodes 
2012 Up All Night Casey Brinkley Episode: "Preschool Auction" 
2013 Westside Robbie Carver Television Movie 
2013–2019 Brooklyn Nine-Nine Detective Keith 'The Vulture' Pembroke Recurring role; 9 episodes 
2014 American Dad! Unknown Voice role; Episode: "News Glances with Genevieve Vavance" 
2015 Battle Creek Russ Agnew Main role; 13 episodes 
2016 Unbreakable Kimmy Schmidt Bunny Episode: "Kimmy Kidnaps Gretchen!" 
2016–2018 Divorce Tony Silvercreek Recurring role; 6 episodes 
2017–2019 Tangled: The Series Andrew Voice role; 2 episodes 
2019 Berlin Station Birdman Episode: "The Dream of the Four Policemen" 
2019 Wayne Daddy/Bobby Lucetti Recurring roles; 6 episodes 
2019 American Gods Mr. Town Episode: "The Beguiling Man" 
The contents of this page are sourced from Wikipedia article on 20 Oct 2020. The contents are available under the CC BY-SA 4.0 license.
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