"It would be proof I'm funny, as well as lots of good opportunities like appearing on shows like Seven Days...plus the free magazines are a bonus,"
He described his humour as "deadpan, dark and intellectual" comparing himself, and aspiring to be more like, English stand-up comedian Stewart Lee.
The comedian said at the age of 13 it was Ellen Degeneres who sparked his interest in comedy but it wasn't until his later University years he decided to give it a crack.
"When I went to University my friends kept saying I should do stand-up comedy but I was always too scared people wouldn't find me funny."
In 2015 he finally signed himself up to an open mic night at The Fringe Bar in Wellington.
"I was prepared to be very bad. I remember a guy told be just before I went on that I was probably going to be really terrible which wasn't super encouraging but after it went really well he told me I was really funny," Mr O'Leary said.
After finishing secondary school at Cullinane College in Whanganui Mr O'Leary moved to Wellington to study a bachelor, followed by a masters, in philosophy.
"While I was at Cullinane, a friend gave me a copy of a book called Sophie's World which is about philosophy, and it blew my mind and made me question the religion I had been raised with.
"I go over why I chose to study philosophy in my show this year - I'd say it's the core part of it since philosophy has been such a huge influence on me."
Some Whanganui residents may identify with Ray under the name Matthew as that is his birth name.
Ray was a nickname given to him by his University friends who decided his voice sounded like American stand-up comedian Ray Romano.
"They were 17 and 18 year olds and thought that silly fact was funny so ran with the gag...they'd ask me if a girl I was talking to was my "Debra" etc. But it stuck and now nearly everyone knows me by that name and I even call myself that name," he said.
Mr O'Leary said he has performed twelve shows already in the NZ International Comedy Festival and has six more to go, including both solo and line up shows. He said if he wins the award he will commit to doing a show back in his home-town Whanganui.
In honour of New Zealand comedian Billy T. James the award has been presented annually since 1997. Initially it was an award shared between two until it became a solo award in 2001.
Other nominees are Paul Williams, Li'i Alaimoana, Angella Dravid and Patch Lambert.
