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* ''Series/{{The Twilight Zone|2002}} (2002) as Gordon

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* ''Series/{{The Twilight Zone|2002}} Zone|2002}}'' (2002) as Gordon



* ''Series/UpAllNight
* ''Series/BrooklynNineNine (2013-2019) as Keith Pembroke

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* ''Series/UpAllNight
* ''Series/BrooklynNineNine
''Series/BrooklynNineNine'' (2013-2019) as Keith Pembroke


Dean Winters (born July 20, 1964 in New York City, New York) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on ''Series/RescueMe'', ''Series/ThirtyRock'', ''Series/BrooklynNineNine'', and ''Series/LawAndOrderSpecialVictimsUnit''. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.

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Dean Winters (born July 20, 1964 in New York City, New York) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}.''Series/{{Oz}}''. He's also recognisable for regular and recurring roles on ''Series/RescueMe'', ''Series/ThirtyRock'', ''Series/BrooklynNineNine'', and ''Series/LawAndOrderSpecialVictimsUnit''. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.commercials.

!!His film roles include:
* ''Film/ConspiracyTheory'' (1997) as Cleet (film debut)
* ''Film/HellraiserHellseeker'' (2002) as Trevor
* ''Film/PSILoveYou'' (2007) as Tom
* ''Film/JohnWick'' (2014) as Avi
* ''Film/TeenageMutantNinjaTurtlesOutOfTheShadows'' (2016) as Bartender
* ''Film/RoughNight'' (2017) as Detective Frazier

!!His TV and serial roles include:
* ''Series/NYPDBlue'' (1996) as Larry
* ''Series/{{Millennium}}'' (1997-1999) as young Michael Lanyard[=/=]Mr. Crocell
* ''Series/{{Oz}}'' (1997-2003) as Ryan O'Reily
* ''Series/LawAndOrderSpecialVictimsUnit'' (1999-2019) as Brian Cassidy
* ''Series/ThirdWatch'' (2002) as Bill Stram
* ''Series/{{The Twilight Zone|2002}} (2002) as Gordon
* ''Series/RescueMe'' (2004-2011) as Johnny Gavin
* ''Series/CSIMiami'' (2005) as Raymond Caine
* ''Series/ThirtyRock'' (2006-2012) as Dennis Duffy
* ''Series/LawAndOrderCriminalIntent'' (2008) as Mike Stoat
* ''Series/TerminatorTheSarahConnorChronicles'' (2008-2009) as Charley Dixon
* ''Series/UpAllNight
* ''Series/BrooklynNineNine (2013-2019) as Keith Pembroke
* ''WesternAnimation/AmericanDad'' (2014) as Edward
* ''Series/BattleCreek'' (2015) as Russ Agnew
* ''Series/UnbreakableKimmySchmidt'' (2016) as Bunny
* ''WesternAnimation/TangledTheSeries'' (2017-2019) as Andrew
* ''Series/BerlinStation'' (2019) as Birdman
* ''Series/{{Wayne}}'' (2019) as Daddy[=/=]Bobby Lucetti
* ''Series/AmericanGods'' (2019) as Mr. Town
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!!Tropes related to him:
* TypeCasting: Many of his roles are detectives in police procedural and crime drama shows.


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!Notable Roles
{{Oz}} as Ryan O'Reily 1997-2003

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!Notable Roles
{{Oz}} as Ryan O'Reily 1997-2003
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{{Oz}} as Ryan O'Reily 1997-2003

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\n {{Oz}} as Ryan O'Reily 1997-2003


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!Notable Roles

{{Oz}} as Ryan O'Reily 1997-2003


Dean Winters (born July 20, 1964) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on ''Series/RescueMe'', ''Series/ThirtyRock'', ''Series/BrooklynNineNine'', and ''Series/LawAndOrderSpecialVictimsUnit''. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.

to:

Dean Winters (born July 20, 1964) 1964 in New York City, New York) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on ''Series/RescueMe'', ''Series/ThirtyRock'', ''Series/BrooklynNineNine'', and ''Series/LawAndOrderSpecialVictimsUnit''. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.


Dean Winters (born July 20, 1964) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on ''Series/RescueMe'', ''Series/ThirtyRock'', ''Series/BrooklynNineNine'', and ''Series/LawAndOrderSpecialVictimsUnit''. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.

to:

[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/dean_winters.jpg]]

Dean Winters (born July 20, 1964) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on ''Series/RescueMe'', ''Series/ThirtyRock'', ''Series/BrooklynNineNine'', and ''Series/LawAndOrderSpecialVictimsUnit''. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.commercials.
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Dean Winters (born July 20, 1964) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on ''Series/RescueMe'', ''Series/ThirtyRock'', and ''Series/LawAndOrderSpecialVictimsUnit''. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.

to:

Dean Winters (born July 20, 1964) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on ''Series/RescueMe'', ''Series/ThirtyRock'', ''Series/BrooklynNineNine'', and ''Series/LawAndOrderSpecialVictimsUnit''. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.


Dean Winters (born July 20, 1964) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on Series/RescueMe, Series/ThirtyRock and Series/LawAndOrderSpecialVictimsUnit. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.

to:

Dean Winters (born July 20, 1964) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on Series/RescueMe, Series/ThirtyRock ''Series/RescueMe'', ''Series/ThirtyRock'', and Series/LawAndOrderSpecialVictimsUnit.''Series/LawAndOrderSpecialVictimsUnit''. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.

Added DiffLines:

Dean Winters (born July 20, 1964) is an American actor perhaps best known for his starring role as the manipulative, Irish-American career criminal Ryan O'Reily on the critically acclaimed prison drama Series/{{Oz}}. He's also recognisable for regular and recurring roles on Series/RescueMe, Series/ThirtyRock and Series/LawAndOrderSpecialVictimsUnit. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.

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