‘Oz’ Characters Examined Part 16 – Cyril O’Reily

Ongoing for 25 total entries, I will be examining the best and most memorable figures from Oz. The prison show was HBO’s first venture into dramatic television, making the series a critical point of progress for the network. Many cast members went on to have bigger careers that partially spawned due to excellence on Oz. The majority of TV shows, past and current, don’t provide enough characters to justify a list of this length. 25 feels like an ideal total that should please fans of the show in addition to detailing a reasonable number of top notch personalities.

Subjective lists are inherently debatable as personal tastes and individual responses determine how a given character is viewed. In other words, disagreements/omissions will be a reality. The majority of days (weekends included) will feature either one or two articles from this list being published. Exceptions will be if I have an interview or otherwise important project to publish, in which case the Oz series may take a brief break. All prior entries will be linked at the bottom of every fresh article. If you’re a fan of the show and appreciate this project, please promote it widely and spread the word. Pop Culture Spin appreciates your efforts. Up next in the list, we have Cyril O’Reily, played by Scott William Winters.

The brother of fictional TV creation Ryan O’Reily, the brother of real life figure Dean Winters, Cyril O’Reily/Scott William Winters formed together to create possibly the most sympathetic individual in Oz. The background on Cyril was that he suffered brain damage after participating in a fight during his criminal lifestyle. I didn’t mention this in my Gloria Nathan piece since I was saving it for Cyril’s piece, but Cyril’s biggest moment was killing Nathan’s husband on orders from Ryan.

This made Ryan and Nathan’s love connection all the more unlikely, but more importantly, it landed Cyril behind bars. Throughout his incarceration, Cyril was raped, beaten, and all together put through the ringer in a world of molestation and mayhem that was at times nearly impossible to watch. Even with Ryan’s protection, Cyril simply wasn’t built to last in a prison environment. One of the greatest Oz scenes was when the inmates collectively protested Cyril’s impending execution by pounding on their cells.

Sadly, Cyril was executed in the end. A great point of debate is whether or not Cyril was mentally aware enough to understand the weight of his last moments. Ryan chose the route of beating around the bush and handling Cyril with kid gloves, but once the reality became clear, I tend to believe Cyril knew what was happening. Regardless of where you fall on this debate spectrum, the reality prevails that Cyril’s death was a gut wrenching experience that left a lasting impression. I, for one, was bothered by this execution to the point in which I felt I was watching more than just a show. That’s the mark of great entertainment. Well done, Cyril.

Published Entries of my Examining Oz Characters List
Part 1 – Simon Adebisi / Part 2 – Father Ray Mukada / Part 3 – Chris Keller
Part 4 – Diane Whittlesbey / Part 5 – Bob Rebadow / Part 6 – Augustus Hill
Part 7 – Jaz Hoyt / Part 8 – Ryan O’Reily / Part 9 – Arnold “Poet” Jackson
Part 10 – Sister Peter Marie Reimondo / Part 11 – Shirley Bellinger / Part 12 – Miguel Alvarez
Part 13 – Warden Leo Glynn / Part 14 – Chucky Pancamo / Part 15 – Gloria Nathan
Part 16 – Cyril O’Reilly / Part 17 – Governor James Devlin / Part 18 – Kareem Said
Part 19 – Kenny Wangler / Part 20 – Vernon Schillinger / Part 21 – Agamemnon Busmalis
Part 22 – Tim McManus / Part 23 – Enrique Morales / Part 24 – Burr Redding / Part 25 – Tobias Beecher