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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 Oz. He's also recognisable for regular and recurring roles on Rescue Me, 30 Rock, Brooklyn Nine-Nine, and Law & Order: Special Victims Unit. He can also be seen as the character "Mayhem" in a series of Allstate Insurance commercials.
His brother is actor Scott William Winters.
His film roles include:
- Conspiracy Theory (1997) as Cleet (film debut)
- Hellraiser: Hellseeker (2002) as Trevor
- P.S. I Love You (2007) as Tom
- John Wick (2014) as Avi
- Teenage Mutant Ninja Turtles: Out of the Shadows (2016) as Bartender
- Rough Night (2017) as Detective Frazier
- The Out-Laws (2023) as Vince Millen
His TV and serial roles include:
- NYPD Blue (1996) as Larry
- Millennium (1996) (1997-1999) as young Michael Lanyard/Mr. Crocell
- Oz (1997-2003) as Ryan O'Reily
- Law & Order: Special Victims Unit (1999-2019) as Brian Cassidy
- Third Watch (2002) as Bill Stram
- The Twilight Zone (2002) as Gordon
- Rescue Me (2004-2011) as Johnny Gavin
- CSI: Miami (2005) as Raymond Caine
- 30 Rock (2006-2012) as Dennis Duffy
- Law & Order: Criminal Intent (2008) as Mike Stoat
- Terminator: The Sarah Connor Chronicles (2008-2009) as Charley Dixon
- Brooklyn Nine-Nine (2013-2019) as Keith Pembroke
- American Dad! (2014) as Edward
- Battle Creek (2015) as Russ Agnew
- Unbreakable Kimmy Schmidt (2016) as Bunny
- Tangled: The Series (2017-2019) as Andrew
- Berlin Station (2019) as Birdman
- Wayne (2019) as Daddy/Bobby Lucetti
- American Gods (2019) as Mr. Town
Tropes related to him:
- Typecasting: Many of his roles are detectives in police procedural and crime drama shows.
