Funny In Failure

#281: Ray O'Leary - Powering Through


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Ray O’Leary is a comedian and writer. The Kiwi comic known for his deadpan delivery and iconic grey suit, Ray has been nominated two years running for Best Male Comedian by the New Zealand Comedy Guild, and in 2022 he picked up a win for Best Joke and Best TV Comedy Performance, after being nominated for Best TV Comedy Performance the previous three years. Additionally, he has been twice nominated for New Zealand Comedy Festival’s prestigious Billy T James Award.

His razor-sharp wit has seen him perform across both sides of the Tasman and tour sold-out runs in Christchurch, and Auckland & Wellington as part of the New Zealand Comedy Festival. He has also performed alongside top comedic talent including Flight of the Conchords and Rhys Darby.

Ray is a staple on Australasian television screens and can be seen on Ten’s Have You Been Paying Attention?, Thank God You’re Here, Cheap Seats, and SBS’ Patriot Brains, hosted by the UK’s Bill Bailey and Sue Perkins. He is a regular writer for Cheap Seats, Have You Been Paying Attention? and in NZ, Ray regularly appears and writes for 7 Days, Have You Been Paying Attention and much more.

Ray can be heard on the philosophy podcast Socrates Walks Into A Bar, which won Best Comedy Podcast at the NZ Podcast Awards in 2022. He was also a regular on The Spinoff’s hit Dungeons and Dragons podcast Waterdeep Mountain High.

In 2023, Ray made his Australian debut to sold out audiences with his new show, Everything Funny All The Time Always and was nominated for Best Newcomer at the Melbourne International Comedy Festival. Ray continued a string of sold out shows throughout New Zealand and added to his TV credits as a contestant on season 4 of Taskmaster NZ.

In 2024, Ray returned to the live stage, touring the UK with Melanie Bracewell and followed up with his new show, Your Laughter Is Just Making Me Stronger, throughout Australia, New Zealand and Edinburgh Fringe Festival.

He is currently touring his new show throughout the UK, Australia and New Zealand. ‘Laughter? I Hardly Know Her’ is sure to be another smash hit for the comedy legend in the two-piece suit and then, he can get back to passing on the message he promised to keep.

We chat about being a part of the new wave of NZ comedy, Thank God You’re Here, his magical suit, moving to Australia, jealousy and insecurity, success, working in prison correction policy, Wil Anderon’s kindness, nerves & anxiety, his comedy voice and his master’s in philosophy.

Check Ray out on:

Instagram: https://www.instagram.com/rayolearycomedy

https://www.facebook.com/rayolearycomedy

https://www.youtube.com/channel/UCjNiWfFOMy0K9Ukzo5RAwrA  Tiktok: https://www.tiktok.com/@rayolearycomedy  X/ Twitter: https://x.com/rayolearycomedy Comedy tickets: https://www.livenation.com.au/ray-o-leary-tickets-adp1406844 -------------------------------------------

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Funny In FailureBy Michael Kahan

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