• Home
  • /
  • Film
  • /
  • Dean Winter | Facts, American Actor, Age, Stats, Career, Biography, Personal Life

Dean Winter | Facts, American Actor, Age, Stats, Career, Biography, Personal Life


IntroAmerican actor
IsActor, Film actor, Television actor
FromUnited States of America
TypeFilm, Television, Stage and Radio
Birth20 July 1964, New York City
Age55 years
StatsHeight: 1.8542 m


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.


Winters was born in New York City, New York. He has three siblings: actor Scott William Winters, writer Bradford Winters, and 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 Sergeant 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.

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 agency Leo Burnett 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 cancelled in May 2015.

Most recently, Winters has reprised his role on Brooklyn Nine-Nine as The Vulture and had a supporting role as a divorce attorney on the HBO series Divorce.


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.



  • Conspiracy Theory (1997)
  • Lifebreath (1997)
  • Firehouse (1997; TV film)
  • Undercover Angel (1999)
  • Snipes (2001)
  • Bullet in the Brain (2001)
  • Hellraiser: Hellseeker (2002; direct-to-video)
  • Strip Search (2004; TV film)
  • Brooklyn Bound (2004)
  • Love Rome (2004)
  • Bristol Boys (2005)
  • Dead Calling (2006)
  • P.S. I Love You (2007)
  • Winter of Frozen Dreams (2009)
  • Splinterheads (2009)
  • 7 to the Palace (2009)
  • Today’s Special (2009)
  • The Devil You Know (2013)
  • John Wick (2014)
  • Teenage Mutant Ninja Turtles: Out of the Shadows (2016)

TV Series

  • Homicide: Life on the Street (1995–96)
  • NYPD Blue (1996)
  • Millennium (1997–99)
  • Oz (1997–2003) (main role)
  • New York Undercover (1998)
  • Sex and the City (1999)
  • Law & Order: Special Victims Unit (1999–2000, 2012–14)
  • Deadline (2001)
  • Third Watch (2002)
  • The Twilight Zone (2002) (Episode: “Future Trade”)
  • CSI: Miami (2005)
  • Rescue Me (2004–11)
  • 30 Rock (2006–13)
  • Law & Order: Criminal Intent (2008)
  • Terminator: The Sarah Connor Chronicles (2008–09) (main role)
  • Life on Mars (2008–09)
  • Happy Town (2009)
  • Up All Night (2012)
  • Brooklyn Nine-Nine (2013–15)
  • Battle Creek (2015) (lead role)
  • Unbreakable Kimmy Schmidt (2016)
  • Divorce (2016)

Music Videos

  • Bonnie & Shyne – Shyne feat. Barrington Levy (2001)
  • Ravitz, Justin (2008-03-17). “Bloomberg Films ’30 Rock’ Cameo”. The Huffington Post. Retrieved 2008-03-17.
Spread the love

Leave a Reply