Dean Winters

He also appeared in the 2023 Netflix film The Out-Laws and the 2024 AMC series Monsieur Spade.

• Birth Name — Dean Gerard Winters • Born — 20 July 1964 • Birthplace — New York City, U.S. • Occupation — Actor • Years Active — 1995–present • Relatives — Scott William Winters (brother)

Winters was born in New York City on July 20, 1964. He was raised on Long Island. 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. He attended Chaparral High School and graduated from Brophy College Preparatory, a Jesuit school in Phoenix, in 1982, and from Colorado College in 1986.

Winters' first credited on-camera appearance was on Homicide: Life on the Street. Winters had met creator Tom Fontana while working as a bartender, eventually agreeing to appear on a three-episode arc. Fontana subsequently wrote the part of Ryan O'Reily with Winters in mind for Oz, appearing on 56 episodes between 1997 and 2003. Following Oz's conclusion, Winters had a recurring role on Rescue Me, playing Johnny Gavin between 2004 to 2011. Winters has appeared in two of the Law & Order 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". He also made an appearance in Season 2 of the television series Sex and the City 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, and also became Captain Olivia Benson's love interest. He has also made guest appearances on Third Watch, NYPD Blue, CSI: Miami and as Dennis Duffy in 30 Rock. He starred in the 1999 romantic comedy Undercover Angel with Yasmine Bleeth and the 2002 direct-to-video horror film 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. He also played Charley Dixon, Sarah Connor's love interest, in Terminator: The Sarah Connor Chronicles. Winters was cast in the ABC drama pilot Happy Town, from the creators of October Road, but was replaced by Steven Weber after shooting the pilot. Winters was away from acting until 2010, when Tina Fey brought him back to 30 Rock. 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 as The Vulture and had a supporting role as a divorce attorney on the HBO series Divorce. In 2018, he was cast as Mr. Town in the second season of Starz's American Gods. In 2019, he appeared in the film Framing John DeLorean.

Winters has neuropathy, 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 of two of his toes and half of one of his thumbs. Winters is a distant cousin to American singer Dick Valentine, lead singer of the rock band Electric Six.

• Year — Title — Role — Notes • 1995–1996 — Homicide: Life on the Street — Tom Marans — 3 episodes • 1996 — NYPD Blue — Larry — Episode: "Where'd the Van Gogh?" • The Playroom — Unknown — Television film • 1997 — Firehouse — Nick Wilkinson • 1997, 1999 — Millennium — Young Michael Lanyard/Mr. Crocell — 2 episodes • 1997–2003 — Oz — Ryan O'Reily — Main role, 56 episodes • 1998 — New York Undercover — Paul Delaney — Episode: "Rat Trap" • 1999 — Sex and the City — John McFadden — Episode: "The Fuck Buddy" • Saturday Night Live — Ryan O'Reily — Uncredited; Episode: "Jerry Seinfeld/David Bowie" • 1999–2000, 2012–2014, 2017–2019, 2025 — Law & Order: Special Victims Unit — Detective Brian Cassidy — Recurring role (seasons 1, 13–15, 19–20, 27), 32 episodes • 2001 — Deadline — Des Lonegan — Episode: "Shock" • 2002 — Third Watch — Bill Stram — Episode: "The Unforgiven" • The Twilight Zone — Gordon — Episode: "Future Trade" • 2004 — Strip Search — Ned McGarth — Television film • 2004–2007, 2009, 2011 — Rescue Me — Johnny Gavin — Main role (seasons 1–4), 30 episodes; recurring role (seasons 5, 7), 3 episodes • 2005 — CSI: Miami — Raymond Caine — Episode: "10-7" • 2006, 2008–2012 — 30 Rock — Dennis Duffy — Recurring role, 15 episodes; Nominated – Gold Derby Award for Best Guest Actor in a Comedy Series; Nominated – Online Film & Television Association Award for Best Guest Actor in a Comedy Series • 2008 — Law & Order: Criminal Intent — Mike Stoat — Episode: "Purgatory" • 2008–2009 — Terminator: The Sarah Connor Chronicles — Charley Dixon — Recurring role, 9 episodes • Life on Mars — Vic Tyler — 3 episodes • 2012 — Up All Night — Casey Brinkley — Episode: "Preschool Auction" • 2013 — Westside — Robbie Carver — Television film • 2013–2015, 2017, 2019 — Brooklyn Nine-Nine — Detective Keith 'The Vulture' Pembroke — Recurring role, 9 episodes • 2014 — American Dad! — Edward — Voice role, episode: "News Glances with Genevieve Vavance" • 2015 — Battle Creek — Russ Agnew — Main role, 13 episodes • 2016 — Unbreakable Kimmy Schmidt — Bunny — Episode: "Kimmy Kidnaps Gretchen!" • 2016, 2018 — Divorce — Tony Silvercreek — Recurring role, 6 episodes • 2017, 2019 — Rapunzel's Tangled Adventure — Andrew — Voice role, 2 episodes • 2019 — Berlin Station — Birdman — Episode: "The Dream of the Four Policemen" • Wayne — Daddy/Bobby Lucetti — Recurring role, 6 episodes • American Gods — Mr. Town — Episode: "The Beguiling Man" • City on a Hill — Ralph Hook — Episode: "It's Hard to Be a Saint in the City" • 2021 — Girls5eva — Nick — 4 episodes • 2022 — Joe vs. Carole — Jeff Lowe — Miniseries, 3 episodes • 2024 — Monsieur Spade — Father Morgan — Miniseries, 2 episodes • So Help Me Todd — Dick Franks — 2 episodes • 2026 — The Fall and Rise of Reggie Dinkins — "FDNY: Chicago" Star — Episode: "Put it on Your Cabbage!"

Dean Winters is recorded as actor.