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.
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.
His other current projects are Christmas vs. The Walters, Street Justice, and Krystyna Loboda's comedy Rites & Wrongs.
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.
|1997||Conspiracy Theory||Cleet||film debut|
|1999||Undercover Angel||Harrison Tyler|
|2001||Bullet in the Brain||Bank Robber||Short film|
|2007||P.S. I Love You||Tom|
|2009||Winter of Frozen Dreams||Ken Curtis|
|2010||Vipers in the Grass||Frank Devine||Short film|
|2012||The Worst||Night||Short film|
|2013||The Devil You Know||Jake Kelly|
|2014||Don Peyote||Gun Dealer|
|2016||Teenage Mutant Ninja Turtles: Out of the Shadows||Bartender|
|2017||Rough Night||Detective Frazier|
|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|
|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
|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"|