Dean Winters

Dean Gerard Winters (born July 20, 1964) is an American character actor. He is known for his role as Ryan O'Reily on the HBO prison drama Oz and had roles in TV series Rescue Me, 30 Rock, Sex and the City and Law & Order: Special Victims Unit, as well as portraying "Mayhem" in a series of Allstate Insurance commercials. He co-starred in one season of the CBS Network cop drama series Battle Creek and currently has a recurring role as the Vulture on the comedy series Brooklyn Nine-Nine.

Dean Winters
Winters in October 2010
Dean Gerard Winters

(1964-07-20) July 20, 1964 (age 57)
Years active1995–present
RelativesScott William Winters (brother)

Early lifeEdit

Dean Gerard Winters was born in New York City on July 20, 1964.[1] He was raised on Long Island. He is of Irish and Italian descent, and speaks fluent Italian.[1] He has two brothers, actor Scott and writer Bradford, and a sister, Blair.[2][3] Winters spent his teenage years in Scottsdale, Arizona. He attended Chaparral High School and graduated from Brophy College Preparatory, a Jesuit school in Phoenix, in 1982,[1] and from Colorado College in 1986.[4]


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". He also made an appearance in Season 2 of the television series Sex and the City as John McFadden. 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 Captain Olivia Benson's love interest. He 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.

He 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. Winters played Detective Sam Tyler's father in the US version of Life On Mars. He also played Charley Dixon, Sarah Connor's love interest, in Terminator: The Sarah Connor Chronicles.[5]

Winters performed stand-up comedy at Catch a Rising Star, The Comic Strip, and the Comedy Cellar alongside notable comedians Jerry Seinfeld, Paul Reiser, and Chris Rock. An HBO comedy special led him to the role he portrayed on OZ, the HBO-produced prison drama.

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.[6][7]

On June 20, 2010, Winters was introduced as "Mayhem", a recurring character in a new television and radio advertising campaign for Allstate Insurance created by the advertising agency Leo Burnett Chicago.[8]

He also played Avi in John Wick. 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. Most recently, he reprised his role on Brooklyn Nine-Nine as The Vulture and had a supporting role as a divorce attorney on the HBO series Divorce.[9] In 2018, he was cast as Mr. Town in the second season of Starz American Gods.[10]

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.[11] 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.[11] Winters was away from acting until 2010, when Tina Fey brought him back to 30 Rock, and he started work on the Mayhem television commercial campaign.[11] In 2019, Fey joined Winters in a series of Mayhem commercials.[12]



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
2021 Street Justice Patrick Hannigan Pre-production
2021 Christmas vs. The Walters Brian Walters Post-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 F**k Buddy"
1999 Saturday Night Live Ryan O'Reily Uncredited; Episode: "Jerry Seinfeld/David Bowie"
1999–2019 Law & Order: Special Victims Unit Brian Cassidy Recurring role; 31 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! Edward 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"
2019 City on a Hill Ralph Hook Episode: "It's Hard to Be a Saint in the City"
2021 Girls5eva Nick 3 episodes
TBA Joe Exotic Jeff Lowe Limited series[13]


  1. ^ a b c "Meet Mayhem: The Man Who Made Insurance Interesting". Business Insider. April 19, 2012. Retrieved March 14, 2014.
  2. ^ "Dean Winters' profile at". Turner Classic Movies. Retrieved January 4, 2011.
  3. ^ "Scott William Winters' profile at". IMDb. Retrieved March 20, 2018.
  4. ^ "Dean Winters Married, Wife, Divorce, Girlfriend or Gay". Retrieved March 21, 2018.
  5. ^ "Dean Winters: Charley Dixon". Retrieved 2018-12-13.
  6. ^ Andreeva, Nellie (2009-02-22). "Slew of pilots flesh out casts". Archived from the original on February 27, 2009. Retrieved 2010-05-20.
  7. ^ "Guide". Retrieved 2010-05-20.
  8. ^ "2010: Allstate disrupts insurance industry with introduction of "Mayhem"". Retrieved 2018-12-13.
  9. ^ "Dean Winters: Tony Silvercreek". Retrieved 2018-12-13.
  10. ^ "Dean Winters cast as Mr. Town in the second season of 'American Gods'". Deadline. June 4, 2018. Retrieved July 21, 2018.
  11. ^ a b c "Dean Winters' amazing journey back from death". New York Post. June 18, 2010. Retrieved September 30, 2012.
  12. ^ "Tina Fey takes the driver's seat in Allstate's new Mayhem spots". November 1, 2019.
  13. ^ Otterson, Joe (June 24, 2021). "'Joe Exotic' Peacock Series Casts Dean Winters as Jeff Lowe". Variety. Retrieved June 24, 2021.

External linksEdit