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Dean Winters

Dean Winters

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Also Known As: Died:
Born: July 20, 1964 Cause of Death:
Birth Place: New York City, New York, USA Profession: actor, bartender

Biography CLOSE THE FULL BIOGRAPHY

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...

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.

While on "Oz," Winters did guest shots on network series like "Millennium" and "New York Undercover" (both Fox), playing on the latter series a firefighter suspected of setting blazes who happens to be the brother of one of the resident detectives (Marisa Ryan). Here Winters teamed up with "Oz" co-star Lauren Velez for one 1998 episode, but he would reteam with "Oz" co-star Christopher Meloni for a series, both actors taking roles on the other side of the law, co-starring as detectives on the NBC spin-off "Law & Order: Special Victims Unit" (1999-2000). On this drama, he was cast as Brian Cassidy, an enthusiastic and relatively green detective assigned to this elite unit who gets paired up with veteran Detective Munch (Richard Belzer), late of the Baltimore Police and a character from the acclaimed series "Homicide: Life on the Street." Viewers of "Oz" were interested to see Winters tackle such a different role, playing the idealistic and eager-to-please lawman on this police drama. His character's inability to handle the emotionally harrowing terrain of the Special Victims Unit excused the actor from the series midway into the first season, when he returned to lens the fourth season of "Oz."

Winters' feature work includes a small role in the Julia Roberts and Mel Gibson thriller "Conspiracy Theory" (1997). He subsequently starred as a dissatisfied writer left to care for a little girl who turns out to be his daughter and inspires him to a more fulfilling life in the family drama "Undercover Angel" (filmed in 1998), was released direct-to-video in 2000.

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Filmographyclose complete filmography

CAST: (feature film)

1.
 Rough Night (2017)
3.
 Splinterheads (2009)
4.
 Today's Special (2009)
6.
 P.S. I Love You (2007)
7.
 Strip Search (2004) Ned Mcgrath
8.
 Brooklyn Bound (2004)
9.
 Snipes (2001) Bobby Starr
10.
 Undercover Angel (1999) Harrison Tyler
VIEW THE FULL FILMOGRAPHY

Milestones close milestones

1992:
Began acting in his late 20s after being encouraged by his younger brother to come along to a drama class
1999:
Cast as enthusiastic new detective Brian Cassidy on the NBC drama, "Law & Order: Special Victims Unit"
2004:
Cast as Tommy's (played by Denis Leary) brother, Johnny on the FX drama, "Rescue Me"
1999:
Guest starred as Carrie's 'F*ck Buddy' on HBO's "Sex and the City"
2008:
Had a recurring role as Sam's father in "Life on Mars" (ABC)
2006:
Played a recurring role on "30 Rock" (NBC) as Liz Lemon's former boyfriend
1997:
Played manipulative and crafty inmate Ryan O'Reilly on the HBO prison drama, "Oz"
2008:
Played Sarah Conner's love interest on several episodes of "Terminator: The Sarah Connor Chronicles" (FOX)
1995:
Made TV debut in a recurring role on the NBC police series, "Homicide: Life on the Street"
1998:
Played a firefighter suspected of arson on an episode of FOX's "New York Undercover"
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Notes

Winters on playing calculating prisoner Ryan O'Reilly on "Oz": ". . . [T]he most appealing thing about Ryan to me was his basic survival instincts and how he's able to survive all kinds of situations, 'cause you know he's a dirt bag, he's a cockroach, a manipulator . . . I mean, you know how it is, but let's not lose sight of what we're dealing with here. I mean we are in a prison environment, not a prep school, so the fact that Ryan's always able to stay one step ahead of everybody by doing everything he thinks is necessary and damn the consequences--I mean, who wouldn't want to play that? I've said this before, you know, I try to go through life being a pretty good person, but to be able to play somebody like Ryan is a dream because . . . I mean everyone at some point in their life gets pushed to the point of wanting to feed somebody glass. . . " --quoted in a 1999 interview on HBO's "Oz" website (www.hbo.com/oz)

Family close complete family listing

brother:
Scott William Winters. Divorced.
brother:
Scott William Winters. Actor. Born in July 1966; played Cyril O'Reilly, brother of Dean's character Ryan O'Reilly on "Oz" (HBO).
brother:
Bradford Winters. Screenwriter. Co-wrote episode of "Oz".
brother:
Bradford Winters. Had four; survived him.
sister:
Blair Winters. Survived him.
VIEW COMPLETE FAMILY LISTING

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