Dean Winters (born July 20, 1964) is an American actor, who is known for his roles as Bobby on the YouTube series Wayne, Detective Brian Cassidy on Law & Order: SVU, Detective Russ Agnew on Battle Creek, 'The Vulture' Detective Pembroke on Brooklyn Nine-Nine, Charley Dixon on FOX's Terminator: The Sarah Connor Chronicles, Dennis Duffy on NBC's 30 Rock, Johnny Gavin on FX's Rescue Me, Ryan O'Reily on HBO's Oz. He also portrays "Mayhem" in Allstate commercials.

Filmography

• The Fall and Rise of Reggie Dinkins — "FDNY: Chicago" Star
• 2025Eenie Meanie — Mikey
• 2025Highest 2 Lowest — Det. Higgins
• 2024Justice League: Crisis on Infinite Earths Part Three — Captain Storm (voice)
• Monsieur Spade — Father Morgan
• 2024Zo — Ryan O'Reily, Producer
• 2023The Out-Laws — Vince Millen
• Joe vs Carole — Jeff Lowe
• So Help Me Todd — Dick Frank
• 2021Christmas vs The Walters — Brian Walters
• 2021DC Showcase: The Losers — Capt. Storm (voice)
• Girls5eva — Nick
• 2021Palmer — Jerry
• 2020Lost Girls — Dean Bostick
• City on a Hill — Ralph Hook
• 2019Framing John DeLorean — John Valestra
• Wayne — Bobby
• 2018A Civilized Life — Conway, Producer
• 2018After Everything — Blake
• 2018Father of the Year — Geoff
• American Gods — Mr. Town
• Rapunzel's Tangled Adventure — Andrew (voice)
• 2017Rough Night — Detective Frazier
• Berlin Station — Birdman
• Divorce — Tony Silvercreek
• 2016Teenage Mutant Ninja Turtles: Out of the Shadows — Bartender
• Battle Creek — Detective Russ Agnew
• Unbreakable Kimmy Schmidt — Bunny (voice)
• 2014Don Peyote — Gun Dealer
• 2014John Wick — Avi
• Last Week Tonight with John Oliver — Brett
• Brooklyn Nine-Nine — Keith 'The Vulture' Pembroke
• 2013The Devil You Know — Jake Kelly
• 2012The Worst — Nick
• Up All Night — Casey Brinkley
• 2009Splinterheads — Reggie
• 2009Today's Special — Steve
• 2009Winter of Frozen Dreams — Ken Curtis
• Life on Mars — Vic Tyler
• Terminator: The Sarah Connor Chronicles — Charley Dixon
• 2007P.S. I Love You — Tom
• 30 Rock — Dennis Duffy
• American Dad! — (voice)
• 2005Bristol Boys — Randy
• 2005Brooklyn Bound — Danny
• 2004Love Rome — Dean
• Rescue Me — Johnny Gavin
• 2004Strip Search — Ned McGrath
• CSI: Miami — Raymond Caine
• 2002Hellraiser: Hellseeker — Trevor Gooden
• The Twilight Zone — Gordon
• 2001Bullet in the Brain — Bank Robber
• Law & Order: Criminal Intent — Mike Stoat
• 2001Snipes — Bobby Starr
• 2001Starwater
• Deadline — Des Lonegan
• Law & Order: Special Victims Unit — Brian Cassidy
• Third Watch — Bill Stram
• 1999Undercover Angel — Harrison Tyler
• Sex and the City — John McFadden
• 1997Conspiracy Theory — Cleet
• 1997Lifebreath — Chrystie's Lover
• Oz — Ryan O'Reily
• 1996Firehouse — Nick Wilkinson
• Millennium — Mr. Crocell, Michael Lanyard (joven)
• New York Undercover — Paul Delaney
• Homicide: Life on the Street — Tom Marans
• NYPD Blue — Larry
• Saturday Night Live — Ryan O'Reily (uncredited)
• Old Soul

Appearances as themselves (5)

• 2025I Am Luke Perry — Self
• 2024Chuck Zito: An American Story — Self
• 2015Don't F*#% With John Wick — Self
• 2015John Wick: NYC Noir — Self
• Dream School — Self - Life Skills Teacher/Self - Actor and Allstate 'Mayhem'