Zaryd Wilson caught up with the now Auckland-based comic on his recent trip home and talked about writing for and appearing on 7 Days, the philosophy of comedy and how he got into the game.
There came a point when Ray O'Leary realised it was never going to be quite the right time to give stand up a go.
With a masters in philosophy behind him, O'Leary was working as a bureaucrat in Wellington, writing funny thoughts and observations in a notebook all while the thought of getting into stand-up comedy lingered in the back of his mind.
"I'd been putting it off for a long time saying 'oh, I'll do it when work quiets down'," O'Leary says.
"But I realised work was never going to quiet down so I just had to do it."