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 and starring in the 2014 film John Wick. 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 and education Winters was born in New York City on July 20, 1964. He was raised on Long Island. He is of Irish and Italian descent, and speaks fluent Italian. He has two brothers, actor Scott and writer Bradford, and a sister, Blair. 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, and from Colorado College in 1986.
Career Winters' first credited on-camera appearance was on Homicide: Life on the Street. Winters had met creator Tom Fontana while working as a bartender, eventually agreeing to appear on a three-episode arc. Fontana subsequently wrote the part of Ryan O'Reily with Winters in mind for Oz, appearing on 56 episodes between 1997 and 2003. Following Oz's conclusion, Winters had a recurring role on Rescue Me, playing Johnny Gavin between 2004 to 2011.
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, and also became Captain Olivia Benson's love interest. He has also made guest appearances on Third Watch, NYPD Blue, CSI: Miami and as Dennis Duffy in 30 Rock.
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.
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.
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. In 2019, Fey joined Winters in a series of "Mayhem" commercials.
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.
In 2018, he was cast as Mr. Town in the second season of Starz's American Gods.
In 2019, he appeared in the film Framing John DeLorean.
Personal life 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. Winters is a distant cousin to American singer Dick Valentine, lead singer of the rock band Electric Six.
Filmography Film Year Title Role Notes1997 Conspiracy Theory Cleet Lifebreath Chrystie's Lover 1999 Undercover Angel Harrison Tyler2001 Snipes Bobby StarrBullet in the BrainBank RobberShort film 2002 Hellraiser: Hellseeker Trevor Gooden Direct to video2004 Brooklyn Bound Danny Love Rome Dean2006 Bristol Boys Randy Dead Calling Nick 2007 P.S. I Love You Tom2009 Winter of Frozen Dreams Ken Curtis Splinterheads Reggie Today's Special Steve 2013 The Devil You Know Jake Kelly2014 Don Peyote Gun Dealer John Wick Avi 2016 Teenage Mutant Ninja Turtles: Out of the Shadows Bartender 2017 Rough Night Detective Frazier2018 After Everything Blake Father of the Year Geoff 2019 Framing John DeLorean John Valestra Documentary 2020 Lost Girls Dean Bostick2021 Palmer Jerry Christmas vs. the Walters Brian Walters 2023 The Out-Laws Vince Millen 2024ZORyan O'ReilyShort film Justice League: Crisis on Infinite Earths - Part Three Captain Storm (voice) Direct-to-video 2025 Highest 2 Lowest Det. Higgins
Television Year Title Role Notes 1995–1996 Homicide: Life on the Street Tom Marans 3 episodes1996 NYPD Blue Larry Episode: "Where'd the Van Gogh?" The Playroom UnknownTelevision film 1997 Firehouse Nick Wilkinson 1997, 1999 Millennium Young Michael Lanyard/Mr. Crocell 2 episodes 1997–2003 Oz Ryan O'Reily Main role, 56 episodes 1998 New York Undercover Paul Delaney Episode: "Rat Trap"1999 Sex and the City John McFadden Episode: "The Fuck Buddy" Saturday Night Live Ryan O'Reily Uncredited; Episode: "Jerry Seinfeld/David Bowie" 1999–2000,2012–2014,2017–2019, 2025 Law & Order: Special Victims Unit Detective Brian Cassidy Recurring role (seasons 1, 13–15, 19–20, 27), 32 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 2004–2007,2009, 2011 Rescue Me Johnny Gavin Main role (seasons 1–4), 30 episodes; recurring role (seasons 5, 7), 3 episodes 2005 CSI: Miami Raymond Caine Episode: "10-7" 2006, 2008–2012 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 Life on Mars Vic Tyler 3 episodes 2012 Up All Night Casey Brinkley Episode: "Preschool Auction" 2013 Westside Robbie Carver Television film 2013–2015,2017, 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 Rapunzel's Tangled Adventure Andrew Voice role, 2 episodes2019 Berlin Station Birdman Episode: "The Dream of the Four Policemen" Wayne Daddy/Bobby Lucetti Recurring role, 6 episodes 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 4 episodes 2022 Joe vs. Carole Jeff Lowe Miniseries, 3 episodes2024 Monsieur Spade Father Morgan Miniseries, 2 episodes So Help Me Todd Dick Franks 2 episodes2026 The Fall and Rise of Reggie Dinkins "FDNY: Chicago" Star Episode: "Put it on Your Cabbage!"
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