"Being in my Collegiate uniform, when you've spent five years being called a 'ringy', or people saying you're from poofters' palace, anything a drunk guy from Auckland yells at you on stage is not nearly as threatening," he said.
"I live in Auckland now, I'm afraid, as much as I would love to live in Whanganui when I look at house prices - the nice places you could buy in St John's Hill for less than a one-bedroom apartment here.
"And I dig the vibe of Whanganui - it's a cool place."
Reviews have praised Stellingwerf's laid-back manner and intellectual banter.
Mat Campbell from Keeping Up With NZ said Stellingwerf was "at times undeniably lovable".
"His references are far and wide, with everything from Anne Frank to cougars getting a going over".
Stellingwerf's act was also described as "utterly filthy".
Making his debut in 2012, the 28-year-old has won a number of awards, including best comedian at Dunedin Fringe Festival, and has appeared on TV3's AotearoHA.
Stellingwerf's producer Taylor McLeod said the comedian's stage confidence hid a shy personality.
"My first impression of Matt ... he was the cowardly lion. He took a while to come out of his shell, but he's shown huge potential with a kind of intelligent humour that's sometimes hard to pull off," she said.
A four-time NZ Comedy Guild award winner, Stellingwerf is taking his stage show to Auckland, Wellington, Palmerston North, Christchurch and Dunedin over the next two months.
The winner of the Billy T James award will be decided at Last Laughs on May 15.