- O'Callaghan has played Stephen Dedalus for Bloomsday on Broadway.
- He did voice over work on the movie Gangs of New York directed by Martin Scorsese.
- He took part in the radio series LA Shorts at The Getty Musuem. He read alongside Alec Baldwin, Angelica Houston, Dustin Hoffman and Ed Begley.
- He played a Doctor for Benylin Cough Syrup.
- O'Callaghan was directed by Mark Romanek for the New Honda Ad Campaign.
- He was the lead in the Olympus ad campaign Cropped Tourists which was awarded the Gold Lion at Cannes directed by Noam Murro.
- The Lonesome West - Martin McDonaghs epic at The Odyssey Theatre in Los Angeles - gave him a chance to play a priest - Father Welsh Walsh Welsh.
- John Played Cathage in the Canadian Premiere of Marina Carr's By the Bog of Cats.
- He stripped to 600 women every night at The New Yorker in Toronto. Playing Declan in Ladies Night - The Live Full Monty.
- He starred in Howie The Rookie by Mark O'Rowe (Intermission)directed by Nancy Malone in New York, Toronto(A Canadian Premiere) and Los Angeles(Premiere).
- The Critically acclaimed North American Premiere of the one man show Rum and Vodka written by Conor McPherson(The Weir)was performed by O'Callaghan to sold out houses in New York, Toronto and Los Angeles. He was invited to perform and record the show for HBO Executives at the HBO workspace directed by Jay Leggett.
- In 2006 he starred in The Affairs of Anatol at Artword Theatre. He played Anatol and had an affair with 7 of Canada's Leading Ladies.
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