Watch Dean Winters Online

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.

• Terminator: The Sarah Connor Chronicles (2008) (TV series)
• 30 Rock (2006, 2008) (TV series)[1] ("Jack Meets Dennis", "Tracy Does Conan", "The Break Up", "Subway Hero")
• PS, I Love You (2007)
• Rescue Me (2004) (TV series) (2004–2006)
• Hellraiser: Hellseeker (2002) (V)
• Law & Order: Special Victims Unit (1999) (TV series) (1999–2000)
• Undercover Angel (1999)
• Conspiracy Theory (1997)
• Oz (1997–2003) (TV series)