Dean Winters was born on July 20, 1964 in New York City. He has three younger siblings: a poet and writer named Bradford, a sister named Blair, and a fellow actor named Scott. Dean is best known for the role of Ryan O’Reily, a Machiavellian inmate and plotter in the HBO TV show Oz. Scott co-starred together with him and also played the role of his younger brother on the show. Other television series that Dean has acted in include Sex and the City, Law and Order: Special Victims Unit,
and 30 Rock.
He has also had roles in films such as Undercover Angel and Hellraiser: Hellseeker.
Ryan O’Reily is portrayed by Dean Winters in the HBO prison drama television series Oz. He is an Irish-American gangster who was sentenced to life imprisonment, in the wake of a rampage that he went on through the city, one induced by alcohol and drug abuse. Among the various crimes he was charged with is possession of narcotics, possession of a deadly weapon, violating his parole period, and vehicular manslaughter. Ryan is a sly and cunning individual who survives by manipulating people around him, similar to Iago, the villain of the Shakespeare classic Othello.
(Photo courtesy of HBO)