Hailing from Christchurch, heâ€™s this year wrapping up the final year of an acting degree at Unitec and was part of this yearâ€™s Comedy Festival in a show three-person Minority Report, for which he was nominated as Best Newcomer.
He also travelled to the Edinburgh Fringe this year to perform Square Eye Pair with Hamish Parkinson, a show that had won them Best Comedy at the Auckland Fringe in 2011.
Matthewsonâ€™s only relatively recently starting bringing his sexuality into his comedy.
â€śAs soon as I come out on stage, which I usually do in my first line if I'm doing a gig at the Classic, it opens you up to them a bit more I think,â€ť he told GayNZ.com earlier this year.
Matthewson has made it into the final five seeking the Yellow Towel from 15 finalists. He is up against Joseph Moore, Pax, Rose Matafeo and Tom Furniss.
Previous winners of the Billy T Award include gay disabilities advocate and comedian Phillip Patston, while lesbian comedian Urzila Carlson was a finalist last year.
Final performances and judging will take place at Last Laughs, on Sunday 19 May.