In this heartfelt episode of The Pie Guy Podcast, host Matt Walker catches up with his cousin's cousin, Brooklyn native Harry O'Reilly—a veteran actor, director, and writer with over 30 years in Hollywood. From his breakout as Pvt. Michael Duffy in the gritty Vietnam War drama Hamburger Hill (1987) to dishing witty banter as Wes McGregor in the Gen-X rom-com Reality Bites (1994), Harry's career highlights include channeling deadpan frustration as Steven's boss opposite Jim Carrey in The Cable Guy (1996) and suiting up as Special Agent Dansk in the ensemble heist flick Tower Heist (2011).
The two dive into Harry's athletic roots—playing football for the Brooklyn Mariners, boxing, and hooping alongside future NBA legend Chris Mullin—before unpacking his bold pivot from college football scholarship to drama department, studying under legends like Geraldine Page, and landing early gigs without an agent. Expect raw stories of near-misses (like turning down Friends and a callback with Robert Redford for A River Runs Through It), the grind of auditions versus live theater, and hard-won lessons on connecting emotionally to roles over rote memorization. As a devoted dad of three who's stepped back to support his kids (including a budding filmmaker son), Harry reflects on powering down the "hamster wheel" of acting, New York vs. LA vibes, and why residuals from '90s TV beats Broadway pay.
Nostalgic, scrappy, and packed with Gen-X grit, this family-fueled chat—touching on everything from The Godfather to Succession—is a reminder that the best stories come from lived truth. Tune in for laughs, wisdom, and that unmistakable Brooklyn heart.
