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1[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/dean_winters.jpg]]
2
3Dean 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.
4
5His brother is actor Creator/ScottWilliamWinters.
6
7!!His film roles include:
8* ''Film/ConspiracyTheory'' (1997) as Cleet (film debut)
9* ''Film/HellraiserHellseeker'' (2002) as Trevor
10* ''Film/PSILoveYou'' (2007) as Tom
11* ''Film/JohnWick'' (2014) as Avi
12* ''Film/TeenageMutantNinjaTurtlesOutOfTheShadows'' (2016) as Bartender
13* ''Film/RoughNight'' (2017) as Detective Frazier
14* ''[[Film/TheOutLaws2023 The Out-Laws]]'' (2023) as Vince Millen
15
16!!His TV and serial roles include:
17* ''Series/NYPDBlue'' (1996) as Larry
18* ''Series/Millennium1996'' (1997-1999) as young Michael Lanyard[=/=]Mr. Crocell
19* ''Series/{{Oz}}'' (1997-2003) as Ryan O'Reily
20* ''Series/LawAndOrderSpecialVictimsUnit'' (1999-2019) as Brian Cassidy
21* ''Series/ThirdWatch'' (2002) as Bill Stram
22* ''Series/{{The Twilight Zone|2002}}'' (2002) as Gordon
23* ''Series/RescueMe'' (2004-2011) as Johnny Gavin
24* ''Series/CSIMiami'' (2005) as Raymond Caine
25* ''Series/ThirtyRock'' (2006-2012) as Dennis Duffy
26* ''Series/LawAndOrderCriminalIntent'' (2008) as Mike Stoat
27* ''Series/TerminatorTheSarahConnorChronicles'' (2008-2009) as Charley Dixon
28* ''Series/BrooklynNineNine'' (2013-2019) as Keith Pembroke
29* ''WesternAnimation/AmericanDad'' (2014) as Edward
30* ''Series/BattleCreek'' (2015) as Russ Agnew
31* ''Series/UnbreakableKimmySchmidt'' (2016) as Bunny
32* ''WesternAnimation/TangledTheSeries'' (2017-2019) as Andrew
33* ''Series/BerlinStation'' (2019) as Birdman
34* ''Series/{{Wayne}}'' (2019) as Daddy[=/=]Bobby Lucetti
35* ''Series/AmericanGods'' (2019) as Mr. Town
36----
37!!Tropes related to him:
38* TypeCasting: Many of his roles are detectives in police procedural and crime drama shows.

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