Call it Sophie Henderson’s sliding-doors moment. There she was, 24, playing Bailey Wilson, the love-rat lawyer girlfriend of Outrageous Fortune’s West twins, bartending part-time at Auckland’s Basement Theatre, and working weekends at clothing store North Beach.
All Henderson wanted was full-time work in the arts. But when she was offered the job of the Basement’s programme manager, she demurred. After all, it was a small maverick theatre, held together by masking tape and string and frantically trying to raise money for air-conditioning (staff toilets followed a couple of years later).
But Charlie McDermott, Basement co-founder and then general manager, was an entrepreneurial type and persuasive: “He would have gone, ‘Soph, Soph, Soph, we need you! Basement needs you,’ and he promised me we would get Creative New Zealand funding so he could pay me properly. It was definitely a leap of faith in Charlie and in the theatre, but I had kept that retail job through all my acting work. It was my one safe thing left,” she recalls.
McDermott’s sales pitch – and the fact he made good on his promise – was enough to lure Henderson out of the shop. She spent five years at the Basement, keeping the lights on and giving a next generation of theatre-makers the chance to tread its well-used concrete floor.
When Henderson left in 2014, she appeared to be on a well-worn trajectory, from stage to small screen to big screen. She and director husband Curtis Vowell, who met at the Basement in 2007, had received much praise for their 2013 debut feature Fantail, which she wrote and starred in. Then there was the Rose Matafeo movie Baby Done in 2020, and the script for 2021 feature The Justice of Bunny King. Meanwhile, the couple had become parents of two girls.

But Henderson always thought fondly of her years at the Basement. “We had no idea what we were doing,” she says. “We were making it up as we went along, but I got to work with people all day and give them opportunities to put their work on stage. Like, we were putting on 100 shows a year.”
How better to pay homage to those years of long hours and little pay than to write and star in a film about it? To remember all the slightly dodgy, sometimes questionable, stuff she did to save the space, aided and abetted first by McDermott then fellow actor and arts administrator Sam Snedden?
In Workmates, Lucy (Henderson) and Tom (Matt Whelan) have spent years together at small maverick theatre the Crystal Ballroom, but they’re maturing – at least he is – and dealing with illegally installed trapdoors (a true story), malfunctioning sprinklers (also true), and grimly earnest theatre directors (obviously true). That’s not as much fun as it used to be. Nevertheless, Lucy’s hanging on, declaring, ‘I love the Crystal Ballroom but it doesn’t love me back.’ Besides, she might just be in love with Tom and she’s determined to hang on to him, too.

While Workmates has a rom-com vibe, its heart belongs to theatre – it features a couple of them, including the gutted interior of Auckland’s St James and the grander Kiri Te Kanawa Theatre in the Aotea Centre. Henderson started writing it in lockdown, when theatres were dark and she feared places like the Basement would never reopen.
“All of my theatre friends had no work and we worried about whether the theatres would ever recover. I sort of always knew there was a story about my time at the Basement and all the questionable things we did to keep the place open.”
Henderson describes Lucy as the worst version of herself. “She’s not exactly likeable, and that’s good. I think the best storytelling has a character transform and so if they’re not flawed in the beginning, where are they going? I think male characters are often that flawed, but women have to be the strong female character. It’s like we’ve got to look up to them, but no, we don’t. The worse they are, the more they have to learn, and that makes them better characters.”

The original idea was to film on iPhones in empty theatres then edit it together.
“And then we went to the Film Commission for a tiny amount of money,” she says. “They loved the script, they loved the story, and they could see it being a bigger film than we did. They were like, ‘Come on, guys, you need to do this properly’, and told us to come back with a bigger budget.”
Four years on, with Vowell in the director’s chair, Workmates premieres at the NZ International Film Festival before going on general release. As well as being producers, McDermott and Snedden have small roles.
It might have been the months spent writing and filming, reliving all the memories, spending time at the Basement, which doubles as the Crystal Ballroom, and reflecting on all the things she loves about theatre that prompted Henderson’s move into her next role.

She’s just started as artistic director at Silo, the contemporary theatre company that once called the Basement home and gave Henderson her first professional job in 2007. “I thought about it a lot because it is sort of a sideways move,” she acknowledges. “My literary agent [in London, who looks after her film-writing work] was not happy with me at all, but I think she’s supportive now because I’ve got theatre scripts coming at me …”
Henderson finished a screenplay this year, and there’s interest in another from America. If that happens, Henderson says, it’ll change her life. Nevertheless, she’s committed to four years at Silo, piloting its programming and contributing to its strategic direction.
“It’s what I dreamed about doing when I was at drama school; if I could have worked full time in theatre forever, I would have. Silo is my favourite company and has given me the most creatively fulfilling times in my life.
Henderson says she plans to champion playwrights. “I think it’s very hard in this country to have a career as a playwright and I want to lift them up. I also want to look after audiences in order to look after our industry. As a writer, I care deeply about audiences. I think because I come from theatre and have that relationship when you’re on the stage, the audience really matters and you can feel them leaning in or getting bored. When I write, I am always thinking about audience and I think that’s the same with programming.
“If I can build an audience that never skips a show, that completely trusts us and we’re doing attention-seeking stuff that gets them in, then I can put more plays on and give more jobs to people.”
Sophie’s Choice

Henderson won’t have to look far if she needs advice on her new role. Outgoing Silo artistic director Sophie Roberts helms its next show, Mother Play. Roberts, who’s been 10 years in Silo’s top job, intends to freelance as a director and spend more time with son Miro, 2.
“And then I’m cooking up a few little plans, potential plans after that in the theatre sector but for now, I’ll just say watch this space.”
When Roberts joined Silo in 2014, she wanted to focus on new plays, touring work and giving NZ writers and performers greater opportunities. “A big thing that I care about in my own personal practise is women, fem and queer experiences on stage, and how we are platforming those voices. That’s been something that I care a lot about along with seeing a greater variety of people really in the driving seats for those projects.”
Ask Roberts to name the show she’s most proud of and she says everyone has been special and each has taught her something, but The Wolves – starring nine teenage girls – stands out. “I love working with young people and I loved working with a young female cast and watching the kind of transformative power of theatre in those actors. And I loved being part of, you know, a really pivotal point for all of them, whether they go on to pursue theatre or not. That was very significant. Very special.
“I’m really proud of the work where we kind of stuck our neck out, which is, I think, when Silo really is at its best. That’s where the company really thrives.”
Henderson intends to build on Roberts’ work. “She’s been amazing at championing new work and new voices. My dream is that Silo, by the time I leave, is all world premieres. I don’t know if I can do it, but I’m going to try my best. I’ve just commissioned a play in my first week…”
Workmates screens at the NZ International Film Festival from August 1 and goes on general release on August 21.
Silo Theatre presents Mother Play written by Paula Vogel and directed by Sophie Roberts, from September 4 - 20 at Q Theatre.