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Jenna MacMillan is an award-winning filmmaker, producer, and founder of Club Red Productions. Her feature directorial debut “The Snake” will premiere at the 2026 SXSW Film Festival this week. In October, she will, as its executive director, bring Anchor Fest (formerly the Charlottetown Film Festival) to her beloved Prince Edward Island. Ahead, she writes about how both journeys are intrinsically linked in her multi-faceted filmmaking career.
I landed in Austin in 2018 with a rejected film, a half-price badge, and a borrowed bed.
I had just produced my first feature, “A Small Fortune,” in my hometown of Prince Edward Island. We had submitted to SXSW, didn’t get in, and were offered a 50 percent-off voucher instead. My best friend was an Austin-based musician at the time and invited me to crash at her place. So I went anyway, mostly to see what all the fuss was about.
I fell hard.
Not just for the films, though those were bold and weird and funny in ways that felt like permission. I fell for the energy. Music pouring out of doorways, comedians popping up in lineups, filmmakers from everywhere meeting each other between tacos and tech panels. The festival felt less like an industry event and more like a creative ecosystem.
I left with a new dream: to bring that kind of energy back home. To prove you didn’t have to live in Toronto or L.A. to make films that belonged in spaces like this.
I grew up on Prince Edward Island. Nestled on the East Coast of Canada, we are known for a few things: potatoes, oysters, and, most famously, Anne of Green Gables. I got my start in the screen industry, playing Anne herself at age 7 for a “Good Morning America” segment called “The World Next Door” about Canada. That gig turned into a decade of being P.E.I. ‘s sweetheart: greeting motorcoaches, hosting tea parties for Japanese tour groups, and cheerfully embodying the Island’s most famous fictional export.
After film school at Toronto Metropolitan University (then known as Ryerson University), I planned to move home and start my career. But the provincial film tax credits changed, the local industry shrank, and suddenly “go home and build a life in film” was no longer realistic. So I spent the next decade working in Toronto, learning how productions functioned. One of those jobs was on “Anne with an E” — a full-circle moment, yes, but also a reminder that I wanted to make work from the Island, not just about it.
Despite my new roots in Toronto, I kept coming back to the stories and storytellers from P.E.I. I bounced between Toronto and Charlottetown, producing web series and indie features. Every time I worked at home, something lit up inside of me. My heart and brain were on fire.
Prince Edward Island is a weird and wonderful place where theatre, sketch comedy, and live music are everyday fixtures. The party line was there “wasn’t a film industry” in Charlottetown. Eventually, I got tired of hearing that. In 2021, in the middle of a pandemic that had already rewritten all the rules, I decided to plant my flag and help build one. Thankfully, the P.E.I. Film Production Fund returned a month after I did. The timing felt like a wink from the universe.
I poured that energy into my company, Club Red Productions. I produced the whodunit comedy “Who’s Yer Father?” with longtime collaborators, writer-director Jeremy Larter and producer Jason Arsenault. The film broke local box office records (we beat “Taylor Swift’s The Eras Tour”) en route to being the #1 comedy that year at the Canadian box office. Turns out, audiences are hungry to see and laugh at themselves on screen.
Around the same time, another piece of the puzzle clicked into place. While preparing for the world premiere of “Who’s Yer Father?,” Club Red had the opportunity to take over producing the Charlottetown Film Festival. I didn’t realize it immediately, but this was the bridge I’d been looking for. What I loved about SXSW wasn’t just the programming, it was the collision of art forms and industries. So we started building that spirit into our festival: adding an industry conference, folding in comedy, bringing in more live music.
In October of this year, we’re rebranding as Anchor Fest, a multi-genre celebration inspired, in no small part, by my first wide-eyed trip to Austin back in 2018.
‘The Snake‘I started production on my first feature as a director in May 2025, a dark comedy called “The Snake,” written and starring Susan Kent (who co-starred in “Who’s Yer Father?”). It’s about a fortysomething wild child who goes on an absolute tear after getting evicted by her venomous mother (played by “SNL”/”SCTV” legend Robin Duke). The story was funny, messy, touching, and maybe just unhinged enough to feel like something that might belong in Austin.
Premiering at SXSW became the dream. This is where they screen the movies I love, the ones I want to see, the ones I want to make. Audience-first, tonally daring, often insanely funny in ways that can be harder to find at major film festivals. We built our post schedule around hitting that submission deadline and delivered the film the night before it was due.
In late December 2025, I was at our annual Club Red Christmas party, surrounded by the growing P.E.I. film community. I was called to my office by one of my colleagues. We had the news. I thought it was bad. It’s such a tough time in the business now. We’ve all taken the punches. This is one of those times it broke right.
Our world premiere. Austin. SXSW 2026.
The first film from Prince Edward Island to screen there.
Eight years in the making.
A bridge, finally, built both ways.
English (US) ·