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Dean Gerard Winters (born July 20, 1964) is an American actor. He is known for his role as
Ryan O'Reily Ryan O'Reily is a main character in the television series '' Oz''. He was portrayed by Dean Winters from 1997 to 2003, who also played the character in the 2024 short film ''ZO''. Character overview "''Prisoner #97P904: Ryan O'Reily. Convicte ...
on the
HBO Home Box Office (HBO) is an American pay television service, which is the flagship property of namesake parent-subsidiary Home Box Office, Inc., itself a unit owned by Warner Bros. Discovery. The overall Home Box Office business unit is based a ...
prison drama '' Oz'' and his roles in the TV series ''
Millennium A millennium () is a period of one thousand years, one hundred decades, or ten centuries, sometimes called a kiloannum (ka), or kiloyear (ky). Normally, the word is used specifically for periods of a thousand years that begin at the starting ...
'','' Rescue Me'', ''
30 Rock ''30 Rock'' is an American satire, satirical sitcom television series created by Tina Fey that originally aired on NBC from October 11, 2006, to January 31, 2013. The series, based on Fey's experiences as head writer for ''Saturday Night Live' ...
'', ''
Sex and the City ''Sex and the City'' is an American romantic comedy, romantic comedy-drama television series created by Darren Star for HBO, based on Sex and the City (newspaper column), the newspaper column and 1996 book by Candace Bushnell. It premiered in th ...
'', 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 ''Brooklyn Nine-Nine'' is an American police procedural sitcom television series that aired on Fox Broadcasting Company, Fox, and later on NBC, from September 17, 2013, to September 16, 2021, for eight seasons and 153 episodes. Created by Dan G ...
''. He also appeared in the 2023 Netflix film '' The Out-Laws'' and the 2024 AMC series '' Monsieur Spade''.


Early life

Winters was born in
New York City New York, often called New York City (NYC), is the most populous city in the United States, located at the southern tip of New York State on one of the world's largest natural harbors. The city comprises five boroughs, each coextensive w ...
on July 20, 1964. He was raised on
Long Island Long Island is a densely populated continental island in southeastern New York (state), New York state, extending into the Atlantic Ocean. It constitutes a significant share of the New York metropolitan area in both population and land are ...
. 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 Scottsdale is a city in eastern Maricopa County, Arizona, United States, and is part of the Phoenix metropolitan area. Named Scottsdale in 1894 after its founder Winfield Scott (chaplain), Winfield Scott, a retired Chaplain Corps (United States ...
. He attended Chaparral High School and graduated from Brophy College Preparatory, a Jesuit school in Phoenix, in 1982, and from
Colorado College Colorado College is a private college, private liberal arts colleges in the United States, liberal arts college in Colorado Springs, Colorado. Founded in 1874 by Thomas Nelson Haskell in his daughter's memory, the college offers over 40 majors a ...
in 1986.


Career

Winters has appeared in two of the ''
Law & Order ''Law & Order'' is an American police procedural and legal drama television series created by Dick Wolf and produced by Wolf Entertainment and Universal Television, launching the ''Law & Order'' franchise. ''Law & Order'' aired its entire ...
'' 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 In Christianity, Purgatory (, borrowed into English language, English via Anglo-Norman language, Anglo-Norman and Old French) is a passing Intermediate state (Christianity), intermediate state after physical death for purifying or purging a soul ...
". He also made an appearance in Season 2 of the television series ''
Sex and the City ''Sex and the City'' is an American romantic comedy, romantic comedy-drama television series created by Darren Star for HBO, based on Sex and the City (newspaper column), the newspaper column and 1996 book by Candace Bushnell. It premiered in th ...
'' 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 ''Third Watch'' is an American crime drama television series created by John Wells and Edward Allen Bernero that aired on NBC from September 23, 1999, to May 6, 2005, with a total of 132 episodes spanning over six seasons. It was produced ...
'', ''
NYPD Blue ''NYPD Blue'' is an American police procedural television series set in New York City, exploring the struggles of the fictional 15th Precinct detective squad in Manhattan. Each episode typically intertwines several plots involving an ensemble ca ...
'', '' CSI: Miami'' and as Dennis Duffy in ''
30 Rock ''30 Rock'' is an American satire, satirical sitcom television series created by Tina Fey that originally aired on NBC from October 11, 2006, to January 31, 2013. The series, based on Fey's experiences as head writer for ''Saturday Night Live' ...
'' 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 Direct-to-video or straight-to-video refers to the release of a film, television series, short or special to the public immediately on home video formats rather than an initial theatrical release or television premiere. This distribution strat ...
horror film Horror is a film genre that seeks to elicit physical or psychological fear in its viewers. Horror films often explore dark subject matter and may deal with Transgressive art, transgressive topics or themes. Broad elements of the genre include Mo ...
'' 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 The possibility of life on Mars is a subject of interest in astrobiology due to the planet's proximity and similarities to Earth. To date, no conclusive evidence of past or present life has been found on Mars. Cumulative evidence suggests that ...
''. He also played Charley Dixon, Sarah Connor's love interest, in '' Terminator: The Sarah Connor Chronicles''. Winters performed stand-up comedy at Catch a Rising Star,
The Comic Strip The Comic Strip are a group of British comedians who came to prominence in the 1980s. They are known for their television series ''The Comic Strip Presents...'', which was labelled as a pioneering example of the alternative comedy scene. The c ...
, and the Comedy Cellar alongside notable comedians
Jerry Seinfeld Jerome Allen Seinfeld ( ; born April 29, 1954) is an American stand-up comedian, actor, writer, and producer. As a stand-up comedian, Seinfeld specializes in observational comedy. Seinfeld gained stardom playing a semi-fictionalized version ...
,
Paul Reiser Paul Reiser (; born March 30, 1956) is an American actor, comedian, and writer. He played the roles of Michael Taylor in the 1980s sitcom ''My Two Dads'', Paul Buchman in the NBC sitcom ''Mad About You'', Modell in the 1982 film ''Diner (1982 f ...
, and Chris Rock. An
HBO Home Box Office (HBO) is an American pay television service, which is the flagship property of namesake parent-subsidiary Home Box Office, Inc., itself a unit owned by Warner Bros. Discovery. The overall Home Box Office business unit is based a ...
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 Steven Robert Weber (born March 4, 1961) is an American actor and comedian. He is best known for his role as Brian Hackett on the television series '' Wings'', and as Dr. Dean Archer on NBC’s Chicago Med. He also voiced Charlie B. Barkin in '' ...
after shooting the pilot. Winters was away from acting until 2010, when
Tina Fey Elizabeth Stamatina "Tina" Fey (; born May 18, 1970) is an American actress, comedian, writer, and producer. Known for her comedic roles in sketch comedy, television and film, Fey has received List of awards and nominations received by Tina Fe ...
brought him back to ''
30 Rock ''30 Rock'' is an American satire, satirical sitcom television series created by Tina Fey that originally aired on NBC from October 11, 2006, to January 31, 2013. The series, based on Fey's experiences as head writer for ''Saturday Night Live' ...
''. 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 ''Brooklyn Nine-Nine'' is an American police procedural sitcom television series that aired on Fox Broadcasting Company, Fox, and later on NBC, from September 17, 2013, to September 16, 2021, for eight seasons and 153 episodes. Created by Dan G ...
'' as The Vulture and had a supporting role as a divorce attorney on the HBO series ''
Divorce Divorce (also known as dissolution of marriage) is the process of terminating a marriage or marital union. Divorce usually entails the canceling or reorganising of the legal duties and responsibilities of marriage, thus dissolving the M ...
''. In 2018, he was cast as Mr. Town in the second season of
Starz Starz (stylized in all caps as STARZ; pronounced "stars") is an American pay television network owned by Starz Entertainment, and is the flagship property of Starz Inc. Launched in 1994 as a multiplex service of what is now Starz Encore, ...
's ''
American Gods ''American Gods'' (2001) is a fantasy novel by British author Neil Gaiman. The novel is a blend of Americana (culture), Americana, fantasy, and various strands of ancient and modern mythology, all centering on the mysterious and taciturn Shad ...
''. In 2019, he was in the film ''
Framing John DeLorean ''Framing John DeLorean'' is a 2019 American documentary film directed by Don Argott and Sheena M. Joyce and written by Dan Greeney and Alexandra Orton, about the life of John DeLorean. The film stars Alec Baldwin, Morena Baccarin, Josh Char ...
''.


Personal life

Winters has
neuropathy Peripheral neuropathy, often shortened to neuropathy, refers to damage or disease affecting the nerves. Damage to nerves may impair sensation, movement, gland function, and/or organ function depending on which nerve fibers are affected. Neuropa ...
, 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 Amputation is the removal of a Limb (anatomy), limb or other body part by Physical trauma, trauma, medical illness, or surgery. As a surgical measure, it is used to control pain or a disease process in the affected limb, such as cancer, malign ...
of two of his toes and half of one of his thumbs.


Filmography


Film


Television


References


External links

* {{DEFAULTSORT:Winters, Dean 1964 births Living people 20th-century American male actors 21st-century American male actors American amputees American male film actors American male television actors Colorado College alumni Male actors from New York City Male actors from Scottsdale, Arizona American people of Irish descent American people of Italian descent