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Born Funny with Jimmy & Nath

RAY O'LEARY: Smart, Silly, Suited Up

21 Aug 2025

Description

Ray O’Leary is one of New Zealand’s sharpest comedic minds. He's a stand-up sensation, TV panel show regular, and the man who somehow makes a grey suit look edgy. In this laugh-out-loud chat with Jimmy & Nath, Ray spills on his unlikely path from philosophy student to full-time comedian, why he quit his “real job” for the stage, and the moment he realised deadpan could pay the bills. From bombing at his first gig to becoming a fan favourite on Have You Been Paying Attention?, Ray opens up about navigating the comedy world, finding his voice (and tone), and why he secretly loves it when people think he’s being serious. They dive into his love of absurd humour, the art of writing jokes that sound smart but are deeply silly, and how confidence is a work in progress, even when you’re crushing it on stage. TUNE IN AS RAY O’LEARY SITS DOWN WITH JIMMY & NATH TO FIND OUT IF HE WAS BORN FUNNY!See omnystudio.com/listener for privacy information.

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