Dean Winters

Dean Winters Headshot

Actor

Birth Date: July 20, 1964

Age: 59 years old

Birth Place: New York City, New York

Brown-haired, wiry actor Dean Winters got a relatively late start in the business, going along at his younger brother's urging to an acting class at age 27. From there, he discovered a fondness for as well as a proficiency in the craft, and began to land TV guest roles. Among his first professional acting jobs was a recurring role on NBC's "Homicide: Life on the Street," playing the husband of a murdered woman. In subsequent episodes, his character confessed to the murder, and was later featured in a prison riot episode. Winters went from this Fontana/Levinson production to another, landing a regular role on the gritty HBO prison drama "Oz" in 1997. The actor played prisoner Ryan O'Reilly, a manipulative and crafty yet oddly likable inmate whose survival skills have allowed him to enjoy a virtually unvictimized existence in the hellish prison. Not a member of any of the main groups represented at Oswald Correctional Facility, O'Reilly succeeded by playing each faction off of another to achieve his desired end. Winters' performance in the program was consistently compelling, and he was given room to show his skills with his character playing integral parts in some of the series' wilder storylines. A breast cancer survivor, O'Reilly fell so hard for the doctor that diagnosed and treated him that he had his mentally challenged brother (played by his real-life sibling Scott William Winters) on the outside kill her husband. He counts among his other credits the slow murder of a fellow inmate by spiking his food with ground glass, fixing a series of boxing matches by drugging whichever combatant he bet against and insidiously overtaking the drug trade from the established dealing group. Winters' multi-dimensional portrayal of the calculating survivor has made O'Reilly a favorite character among fans despite his obvious despicable qualities, his moving depiction of O'Reilly's struggle with his genuine if twisted love for Dr. Nathan (Lauren Velez) and the fierce protectiveness of his overly trusting newly imprisoned brother Cyril (who landed in Oz because of the murder his brother ordered) serving as particularly strong examples of Winters' acting strength.

Credits

Joe vs. CaroleStream

Actor
Jeff Lowe
Series
2022
33%

Christmas vs. the Walters

Actor
Brian Walters
Movie
2021

GMA3: What You Need to Know

Guest
Show
2020

Framing John DeLorean

Actor
John Valestra
Movie
2019

After Everything

Actor
Blake
Movie
2018

Tangled: The Series

Guest Voice
Andrew
Show
2017

Rough Night

Actor
Detective Frazier
Movie
2017

DivorceStream

Guest Star
Tony Silvercreek
Series
2016
78%

Teenage Mutant Ninja Turtles: Out of the Shadows

Actor
Bartender
Movie
2016

Battle Creek: Extras

Actor
Show
2015

Battle CreekStream

Actor
Russ Agnew
Series
2015
96%

Last Week Tonight With John OliverStream

Guest Star
Brett
Talk
2014

Don Peyote

Actor
Movie
2014

John WickStream

Actor
Avi
Movie
2014
86%

Discovering Mavericks (Bonus Cut)

Actor
Movie
2014

Brooklyn Nine-NineStream

Guest Star
The Vulture
Series
2013
95%

The Devil You Know

Actor
Jake Kelly
Movie
2013

CBS This Morning

Guest
Show
2012

Up All Night

Guest Star
Show
2011

The Talk

Guest
Talk
2010

Access Hollywood Live

Guest
Show
2010

Oz

Actor
Show
2009

Winter of Frozen Dreams

Actor
Ken Curtis
Movie
2009

Splinterheads

Actor
Reggie
Movie
2009

Today's Special

Actor
Steve
Movie
2009

Life on MarsStream

Guest Star
Series
2008

Terminator: The Sarah Connor ChroniclesStream

Guest Star
Series
2008
85%

P.S. I Love You

Actor
Tom
Movie
2007

30 RockStream

Guest Star
Dennis Duffy
Series
2006
78%

Entertainment Tonight Canada

Guest
Show
2005

American DadStream

Guest Voice
Series
2005

Bristol Boys

Actor
Randy
Movie
2005

Rescue MeStream

Actor
Johnny Gavin
Series
2004
89%

Rescue MeStream

Guest Star
Series
2004
89%

Love Rome

Actor
Dean
Movie
2004

CSI: MiamiStream

Guest Star
Series
2002

The Twilight ZoneStream

Actor
Series
2002

Hellraiser: Hellseeker

Actor
Trevor
Movie
2002

Law & Order: Criminal IntentStream

Guest Star
Mike Stoat
Series
2001

Snipes

Actor
Bobby Starr
Movie
2001

Third WatchStream

Guest Star
Series
1999

Law & Order: Special Victims UnitStream

Actor
Brian Cassidy
Series
1999
78%

Law & Order: Special Victims UnitStream

Guest Star
Brian Cassidy
Series
1999
78%

Undercover Angel

Actor
Harrison Tyler
Movie
1999

Sex and the CityStream

Guest Star
John McFadden
Series
1998
70%

OzStream

Actor
Ryan O'Reily
Series
1997
92%

OzStream

Guest Star
Ryan O'Reily
Series
1997
92%

Millennium

Guest Star
Series
1996

New York UndercoverStream

Guest Star
Series
1994

NYPD BlueStream

Guest Star
Larry
Series
1993
83%

News about
Dean Winters