“I don’t want to toot my own horn, but I reckon 30 or 40 per cent of it might be good.”
O’Leary attended Cullinane College before leaving for university in Wellington in 2010.
Becoming a comedian wasn’t on his radar back in his Cullinane College days.
“At high school, I was always quite shy,” O’Leary said.
“When we had to do speeches for NCEA, I was too afraid to speak in front of the class. I had to do it at interval in front of only the teacher.”
When he did crack a joke in class, his mates would yell it out and get all the laughs.
“I would just sit there furious that my joke had been stolen,” O’Leary said.
“It hasn’t happened [as a working comedian], and that’s quite insulting, now I think about it. No-one is bothering.
“Hopefully it’s a sign that they’re so perfectly honed to my voice, no-one could possibly rip them off. They wouldn’t dare.”
O’Leary started doing stand-up in 2015, and won Best Newcomer at the New Zealand Comedy Guild Awards the following year.
He is now a regular on Have You Been Paying Attention? and 7 Days.
Across the ditch, he appears on The Cheap Seats and Have You Been Paying Attention? - Australia.
Last year, he ticked over 600 live gigs.
Performing comedy was a very daunting prospect, with most people being put off because of the fear of public speaking, O’Leary said.
“That goes pretty quickly though - that’s the easiest thing to get over. The tricky part is being funny while you’re up there.
“It looks like Whanganui has developed a really great, supportive [comedy] community. That’s all happened since I left, so it’s hard not to take it personally.”
Despite having so many shows under his belt, the proposition of playing in Whanganui was “quite terrifying”.
“I have a lot of friends and family there, and it’s scary to think they might all come to the show.
“Hopefully, I can put on a good show for them and for all the other fine people of The River City.”
His time in Wellington resulted in a Master’s degree in philosophy.
“Obviously, I’ve put that to great practical use,” O’Leary said.
“I think studying it was important to how I think now, and being able to analyse things and break them apart.”
He said one of the Platonic ideals of comedy was pointing out absurdities in everyday life.
“I love a comic by the name of Norm MacDonald, and he’s got a great line - ‘ID’ is a strange abbreviation, because the I is short for ‘I’, and the D is short for ‘dentification’.”
“It’s something you never think about, but when you hear it you’re like, ‘Of course’.”
O’Leary said MacDonald wanted his comedy to be timeless, something he also worried about.
Jokes about politics or the news could become outdated fast.
“You want to be original, and avoiding the low-hanging fruit helps you stand out.
“Before he even became the presidential nominee, I remember thinking there were too many jokes about Donald Trump.
“Unless you can think of a really original take on him, it’s best to avoid it.”
The one-hour Whanganui show is part of a national tour of dates before O’Leary heads to comedy festivals in Australia.
He will be at the Repertory Theatre on March 17.
