"When I came back, I was like: I hate everything I've ever talked about, so I'm gonna try talking about Dad and life, so I started doing that," Bowen says. "That became Heart Goes Boom, which did really well. It was no longer just about being an obnoxious clown."
Heart Goes Boom was followed up by Head Goes Bang, in which Bowen riffed on his mental health battles, and then It Goes On. All three shows were subsequently condensed into a single 90-minute performance.
"We toured that around arts festivals in New Zealand. It was running really well as a narrative piece and I got to that point where I was like: I want to do something with this, but no one's going to make a special for me."
So Bowen made it himself. Although a fixture of the American comedy scene, specials are relatively rare in New Zealand.
"There's really not the infrastructure there," he says. "It's like: 'Are you Rhys Darby? Great. You should put out a special or a DVD. Are you Dai Henwood? You should also do the same'. I'm not either of those people. I can go toe-to-toe with all my peers, but my peers' profiles are infinitely bigger than mine. For whatever reason. Often through self-sabotage. Ha ha!"
Just as Bowen was prepping the special ready for distribution, the opportunity of a lifetime came via his longtime friend Darby, who tapped Bowen to co-star with him in a comedy pilot for a major US network.
"I got a call from Rhys, and he was like: 'I've got this role for you. It'll be great. Come over. Let's make this piece of madness'. So I came over and we made that."
Details are still under wraps and a decision has yet to be made on whether or not the pilot will become a full series, but the job helped spur Bowen make the move to Los Angeles at the beginning of this year.
"In booking me for the pilot they [sponsored me] on a three-year 0-1 visa. Nothing was happening back home. I love 7 Days and the people that make it, but I don't want to be the 7 Days warm-up guy for the next seven years of my career. I've done it enough. [New Zealand] TV wasn't paying attention to me at all, I was just kind of floating. I could headline a gig but I couldn't get anything else. So I thought well, I would rather be broke and struggling in LA than at home and floundering."
In addition to hitting the local stand-up circuit, Bowen has made some fruitful Hollywood connections through Darby - the day he spoke to TimeOut, he had just come from a pitch meeting at the network where he shot the pilot.
"One of the greatest motivators for moving here is I have Rhys and [his wife] Rosie here, who have just been so incredible throughout my career in supporting me and helping me get through to the next level and climb. Because of the people they know here, and because of Rhys' place in the industry here, being Rhys' best mate, it's the greatest gift you could be given coming into Hollywood."