O'Reilly has appeared in over a hundred films and television episodes, primarily as either the antagonist or as a villain. The television series he has appeared in include Cheers, Darkroom, Knight Rider, Sledge Hammer!, MacGyver, In the Heat of the Night, NYPD Blue, and twice in Dallas. His film appearances include the Jim Carrey film The Mask. He has retired from acting.
O'Reilly made his first appearance in the Star Trek franchise with an appearance in the Star Trek: The Next Generation episode "Manhunt". The character he played in that episode has been referred to both as "Tough guy" and "Scarface". He was then cast as the Klingon Gowron in the episode "Reunion" which saw the character become the new Chancellor of the Klingon Empire. O'Reilly had just finished appearing on stage as Edmund in King Lear and saw similarities between the two characters which resulted in him basing Gowron upon the Shakespearian character. The episode was directed by TNG cast member Jonathan Frakes, and O'Reilly later said that he thought he was hired both for the sense of curiosity he brought to the role and a piercing, unsettling gaze he and others referred to as "that crazy loon eyeball thing".
He went on to appear as Gowron over the course of the next decade in several further episodes of The Next Generation, as well as Star Trek: Deep Space Nine. He also filmed segments for the video game Star Trek: Klingon, which was also directed by Frakes. The game was the first Star Trek game to use real actors, and was awarded the Sci-Fi Universe Reader's Choice Universe Award for Best Achievement in Genre Multi-Media. At the time of filming the game, he had heard a rumour that Michael Dorn was joining the cast of Deep Space Nine. Given the relationship between Gowron and Dorn's character, Worf, O'Reilly thought that this might lead to his return to a Star Trek television series too. Both Dorn and O'Reilly reprised their characters together in the series four opening episode "The Way of the Warrior". O'Reilly also appeared as a different Klingon in the Star Trek: The Next Generation Interactive VCR Board Game, a video cassette-based board game. His likeness was used for three action figures, a life-size poster and several lithographs.

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