Dylan passed away on September 1, 2025, at his home in Pensacola, FL. He was born in Highland Park, IL on January 30, 1969 to John Arthur O’Leary, Jr. and Catherine Miller O’Leary. He grew up in McHenry, IL, where his mother‘s family has deep roots.
An insatiable word guy, Dylan earned his BA in Rhetorical Arts from the University of Illinois and his MFA in Screenplay Writing from Louisiana State University.
Dylan deftly transferred his wide and deep knowledge of mainstream and little-known history, movies, books, and trivia into the Irish tradition of clever storytelling and word smithing. To wit, his numerous and highly entertaining short stories; the two camp films This Darkness and Scouts that he wrote, directed, and starred in; and his graphic novel Dalarna.
His genius meant that he lived on his own terms and could see better ways to do things — he had an incessant need to improve what others had created, such as words, rules for a game, art, or product design.
He was a Renaissance man, a good father, and a good friend. Charming, Witty, visionary, and kind hearted.
A fighter to the end, Dylan is survived by his daughter Malaren A. O’Leary of Pensacola, FL and his sister Anne C. O’Leary of Chapel Hill, NC. He was preceded in death by his parents John and Cathy O’Leary.
His family will hold a celebration of Dylan’s life for friends and family this fall in Pensacola.
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