His parents, the late actor Ray Henwood ONZM, and former district court judge and prominent arts supporter Dame Carolyn Henwood, were founding members of Circa Theatre, and Dai followed in their footsteps. Inspired to learn from drama Professor Phillip Mann, he enrolled in the theatre and film programme, along with courses on comparative and Eastern religions.
His memories of student life were dominated by good times at Eastside Bar, where he met new people and heard fresh ideas. “My parents always said university is about finding out what you don’t know, and Eastside was where I first heard about amazing courses I might have overlooked,” he says.
Studying at Vic in Wellington in the 90s was to experience an “electric” city, a time when Wellington bands like Fat Freddy’s Drop and The Black Seeds were dominating the airwaves. “Victoria was the perfect gateway to the city’s energy, where I made friends and discovered a whole new world. It was such a wonderful moment to be a student in Wellington.”
He got his start in comedy as a student at the University Comedy Competition at Kitty O’Brien’s in Auckland in 1997, performing as a duo called ‘Dai-Anna’ with fellow theatre student Anna Kennedy. “The MC, the late Ewen Gilmour, told us we had something and encouraged us to keep going,” he says. After performing at the Classic Comedy Club, Dai says he was hooked. “As soon as I finished my degree, I moved to Auckland to chase the comedy dream—and I feel blessed that it came true.”
After that, Dai’s career in comedy took off, and he embarked on a hugely successful career in stand-up comedy and TV. A founding member of Aotearoa New Zealand's long-running comedy show 7Days in 2009, and host of Family Feud, Dancing with the Stars and Lego Masters, Dai has become one of our most famous faces, but his success isn’t something he takes for granted.
“To have been part of shaping the comedy landscape in Aotearoa has been an incredible privilege,” he says. He counts performing at Just for Laughs Montreal, full season runs at the Melbourne and Edinburgh Festivals and winning the Billy T Award in 2002 as career highlights. That award is just one of many—he’s also won the prestigious Fred Award twice and won Best Male Comedian at the NZ Comedy Guild several times.
He enjoys the collaborative nature of working in TV and the adrenaline rush of performing live. “Live performing is pure adrenaline — there’s no room for mistakes, and when the show goes well, you feel electric. Every audience gets a unique experience, which makes it so special. TV, on the other hand, is a different discipline. It’s about teamwork, timing, and collaboration, and I love the energy that comes from working with others,” he says.
The entertainment industry in Aotearoa has changed hugely since Dai started performing, and Dai notes there is less money in TV and things are “pivoting”. However, live comedy is thriving, and he recently toured the country to huge success. He says the challenge is convincing global streamers such as Netflix to invest in local content. “Without that, our stories and comedies risk being drowned out in the global market.”
Despite these challenges, he doesn’t discourage those wanting to get into the entertainment industry and advises them to take the leap. “The entertainment industry is like any profession—you move up by putting in the hours and taking opportunities when they come. My dad once told me something that has always stuck: ‘Many people have a similar skill set, but if you’re nice and easy to work with, there’s a good chance you’ll get the next job.’”
Dai was diagnosed with stage four bowel cancer in 2020 and shared the news publicly via The Project in 2023. Last year, he released a book, The Life of Dai, and a three-part documentary Live and Let Die, sharing his cancer journey. “For a couple of years, I kept my diagnosis private. I performed when I could, sticking to my old stand-up material, pretending nothing was wrong—but I realised I wasn’t being authentic.
“When I shared my story, it was cathartic. So many people related and sent love, which made me feel incredibly supported. Sharing my journey has connected me with others facing cancer, and I’m proud that my openness has helped people on what can be a very tough road. It’s taught me that sharing vulnerability can be its own kind of strength,” he says.
In addition to receiving the Distinguished Alumni Award next month, Dai was named an Officer of the New Zealand Order of Merit in the King’s Birthday Honours in June, giving him pause to reflect. “Usually, I’m focused on what’s next, but the Distinguished Alumni Award has made me look back and appreciate how much university shaped me.
“I made lifelong friends, discovered my path, and set the foundations for everything I’ve achieved. Both awards remind me how blessed I am. Plus, they make me smile, thinking that the young man hanging out at Eastside Bar did alright.”