Cyril and Ryan O'Reily
O'Reily is an Irish American gangster sentenced to life imprisonment after he went on a drug and alcohol fuelled rampage through the city. He was charged with crimes including possession of a weapon, possession of narcotics , parole violation and vehicular manslaughter. A cunning sociopath , O'Reily survives in Oz by manipulating everyone around him, using a variety of inmate gangs to get whatever he wants; series creator Tom Fontana has likened him to Iago, the villain of Shakespeare's Othello.
Ryan O'Reily is portrayed by Dean Winters.
Cyril was an Irish American hoodlum like his brother (who's actually his half-brother, as was revealed by Suzanne Fitzgerald ), Ryan , until he was injured in a fight, suffering brain damage and becoming mentally handicapped. In the second season of Oz Cyril murdered the husband of Dr. Gloria Nathan on orders from his brother, who was in love with Dr Nathan. Arriving in prison, Cyril was originally housed with Vernon Schillinger, head of the Aryan Brotherhood. After Schillinger raped Cyril, Ryan got his brother transferred to his own cell. Throughout the series Cyril struck a discordant note as a very trusting and innocent personality in the body of a physically powerful and sometimes violent man. His brother Ryan tried to protect him, and the relationship between the two served as a way of humanizing the otherwise completely amoral Ryan. In the last season of the show, Cyril was executed despite Ryan's multiple attempts to save his brother.
Cyril O'Reily is portrayed by Scott William Winters (Dean Winters brother)