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Dean Winters

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Dean Winters
Winters in October 2010
Born
Dean Gerard Winters

(1964-07-20) July 20, 1964 (age 60)
New York City, U.S.
OccupationActor
Years active1995–present
RelativesScott William Winters (brother)

Dean Gerard Winters (born July 20, 1964) is an American actor. He is known for his role as Ryan O'Reily on the HBO prison drama Oz and his roles in the TV series Millennium, 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 had a recurring role as "The Vulture" on the comedy series Brooklyn Nine-Nine. He also appeared in the 2023 Netflix film The Out-Laws and the 2024 AMC series Monsieur Spade.

Early life

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Winters was born in New York City on July 30, 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] 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.

Career

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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, 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 P.S. 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.[3]

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.[4][5]

Winters was away from acting until 2010, when Tina Fey brought him back to 30 Rock. Also that year, Winters was introduced as "Mayhem", a recurring character in a television and radio advertising campaign for Allstate Insurance created by the advertising agency Leo Burnett Chicago.[6] In 2019, Fey joined Winters in a series of "Mayhem" commercials.[7]

Winters played Avi in John Wick. Winters co-starred in one season of the CBS 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. He had a recurring role on Brooklyn Nine-Nine as The Vulture and had a supporting role as a divorce attorney on the HBO series Divorce.[8]

In 2018, he was cast as Mr. Town in the second season of Starz's American Gods.[9]

In 2019, he was in the film Framing John DeLorean.

Personal life

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Winters has neuropathy, resulting in numbness and sensitivity issues in his hands and feet. In 2009, Winters contracted a bacterial infection and went into cardiac arrest. He underwent multiple surgeries and developed gangrene, resulting in the amputation of two of his toes and half of one of his thumbs.[10][11]

Filmography

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Film

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Year Title Role Notes
1997 Conspiracy Theory Cleet
Lifebreath Chrystie's Lover
1999 Undercover Angel Harrison Tyler
2001 Snipes Bobby Starr
2002 Hellraiser: Hellseeker Trevor Direct to video
2004 Brooklyn Bound Danny
Love Rome Dean
2006 Bristol Boys Randy
Dead Calling Nick
2007 P.S. I Love You Tom
2009 Winter of Frozen Dreams Ken Curtis
Splinterheads Reggie
Today's Special Steve
2013 The Devil You Know Jake Kelly
2014 Don Peyote Gun Dealer
John Wick Avi
2016 Teenage Mutant Ninja Turtles: Out of the Shadows Bartender
2017 Rough Night Detective Frazier
2018 After Everything Blake
Father of the Year Geoff
2019 Framing John DeLorean John Valestra Documentary
2020 Lost Girls Dean Bostick
2021 Palmer Jerry
Christmas vs. the Walters Brian Walters
2023 The Out-Laws Vince Millen
2024 Justice League: Crisis on Infinite Earths - Part Three Captain Storm (voice) Direct-to-video
2025 Highest 2 Lowest TBA Post-production

Television

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Year Title Role Notes
1995–1996 Homicide: Life on the Street Tom Marans 3 episodes
1996 NYPD Blue Larry Episode: "Where'd the Van Gogh?"
The Playroom Unknown Short
1997 Firehouse Nick Wilkinson Television film
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"
Saturday Night Live Ryan O'Reily Uncredited; Episode: "Jerry Seinfeld/David Bowie"
1999 Law & Order: Special Victims Unit Brian Cassidy 9 episodes
2001 Deadline Des Lonegan Episode: "Shock"
2002 Third Watch Bill Stram Episode: "The Unforgiven"
The Twilight Zone Gordon Episode: "Future Trade"
2004 Strip Search Ned McGarth Television film
2004–2011 Rescue Me Johnny Gavin Main role
2005 CSI: Miami Raymond Caine Episode: "10-7"
2006–2012 30 Rock Dennis Duffy Recurring role
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
Life on Mars Vic Tyler 3 episodes
2011–2014 Law & Order: Special Victims Unit Brian Cassidy Recurring role
2012 Up All Night Casey Brinkley Episode: "Preschool Auction"
2013 Westside Robbie Carver Television film
2013–2019 Brooklyn Nine-Nine Detective Keith 'The Vulture' Pembroke Recurring role
2014 American Dad! Edward Voice role; Episode: "News Glances with Genevieve Vavance"
2015 Battle Creek Russ Agnew Main role
2016 Unbreakable Kimmy Schmidt Bunny Episode: "Kimmy Kidnaps Gretchen!"
2016–2018 Divorce Tony Silvercreek Recurring role
2017–2019 Tangled: The Series Andrew Voice role
2018–2019 Law & Order: Special Victims Unit Brian Cassidy Recurring role
2019 Berlin Station Birdman Episode: "The Dream of the Four Policemen"
Wayne Daddy/Bobby Lucetti Recurring roles
American Gods Mr. Town Episode: "The Beguiling Man"
City on a Hill Ralph Hook Episode: "It's Hard to Be a Saint in the City"
2021 Girls5eva Nick 3 episodes
2022 Joe vs. Carole Jeff Lowe Limited series
2024 Monsieur Spade Father Morgan Miniseries
So Help Me Todd Dick Franks Episodes: "Dial M for Margaret" & "Is the Jury Out?"

References

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  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. ^ "Dean Winters: Charley Dixon". IMDb. Retrieved December 13, 2018.
  4. ^ Andreeva, Nellie (February 22, 2009). "Slew of pilots flesh out casts". The Hollywood Reporter. Archived from the original on February 27, 2009. Retrieved January 21, 2022.
  5. ^ "Guide". TheFutonCritic.com. Retrieved May 20, 2010.
  6. ^ "2010: Allstate disrupts insurance industry with introduction of "Mayhem"". thedrum.com. Retrieved December 13, 2018.
  7. ^ "Tina Fey takes the driver's seat in Allstate's new Mayhem spots". adage.com. November 1, 2019.
  8. ^ "Dean Winters: Tony Silvercreek". IMDb. Retrieved December 13, 2018.
  9. ^ "Dean Winters cast as Mr. Town in the second season of 'American Gods'". Deadline. June 4, 2018. Archived from the original on June 12, 2018. Retrieved July 21, 2018.
  10. ^ "Dean Winters is in constant pain from multiple amputations". The Independent. November 2, 2021. Retrieved April 1, 2024.
  11. ^ France, Lisa Respers (November 3, 2021). "Dean Winters living in pain after multiple amputations". CNN. Retrieved April 1, 2024.
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