Willy spent his school years at Auckland Grammar, where he learnt music and classical ballet, then left early to work in a garden centre. While serving as the lead singer of the band Rhythm Method, he decided on a whim to enter a comedy competition hosted by his local bar in 1983. There he met fellow contestants on Dean Butler, Ian Harcourt and Peter Murphy which kick-started his long career in making people laugh. After starting off as a live comedy troupe, the quartet won funding to make the series Funny Business in 1988, which quickly earned rave reviews and inspired a national tour. In the 90s, Willy was involved in TV3's That Comedy Show which was nominated for Best Entertainment Programme in 1995.

In 1998 Willy shifted to another branch of broadcasting: radio. For the next 12 years, he hosted shows for Radio Hauraki alongside ex-Funny Business collaborator Dean Butler.

In April 2016 Willy suffered a stroke, which left him hospitalised. He has written a tell-all memoir called Drink, Smoke, Snort, Stroke..., which has taken him three years to write. Released this month, it's a raw, honest account of what it was like to pioneer New Zealand's stand-up comedy scene in the 1980s.

Willy lives on Auckland's North Shore and has a grown-up daughter, Mahu.