Next in our series of chatting to creatives and casts of Edinburgh Fringe 2026, we catch up with Tom Stilwell who is bringing Blackjack! (and other ways to get lucky) in Your Parents’ Basement to the festival. ”Learn how to finally beat the house! All it takes is basic strategy, a little luck, and three easy payments of $7.77. You don’t even have to leave your parents’ basement. Ever! A darkly comic solo show about luck, delusion and the stories we tell ourselves to keep playing.”
How would you describe your show to someone discovering it for the first time at the Fringe?
It’s a darkly comic blackjack lesson taught by someone who is increasingly unqualified to be giving advice. I use the rules of the game to tell stories about startups, relationships, ambition and cruise ships, all leading to the night I won $100,000 from a $1 bet while living in my parents’ basement. It’s about what happens when the worst decision of your life appears to prove you right.
What moment, idea or frustration first sparked this show into existence?
The spark was realizing that everyone had encouraged me to keep “betting on myself” through failed startups, career changes and disastrous relationships, but the moment I actually won a bet, they told me to stop. I became fascinated by the line between perseverance and addiction, and by how quickly that line moves depending on whether the potential jackpot is socially respectable.
How has the show evolved from its earliest idea to what audiences will see now?
Originally, it was much more like a straightforward autobiographical story about an extraordinary gambling win. Over time, the blackjack lesson became the structure of the whole piece, and the person teaching it became less reliable. The show now begins with the confidence of a game-show host and gradually reveals that the lesson is really a defense mechanism.
What makes Edinburgh Fringe the right place for this show right now?
The Fringe is built around risk. Artists spend money they may never earn back, audiences take chances on strangers, and everyone is hoping they might discover or become the next extraordinary success story. And at a time when online gambling is exploding in the mainstream, it’s exactly the venue for a show about believing the next bet will change everything.
What does bringing this particular show to the Fringe represent for you personally?
I gave up performing because I thought technology and startups were the safer, more sensible path. Bringing this show to Edinburgh is a return to the part of myself I abandoned, funded, somewhat absurdly, by the least sensible decision I ever made. It feels like turning something private and shameful into something communal.
What has been the most unexpectedly challenging part of getting this show to Edinburgh?
The hardest part has been balancing honesty with entertainment. The story is unique and funny, but the consequences were real, and I never want the comedy to become a way of pretending they weren’t. Also blackjack tables are really expensive, so we’re doing an IKEA special.
If audiences leave the venue holding onto one thing, what do you hope it is?
Winning does not prove that a bad bet was good. More broadly, I hope people question the advice to “bet on yourself” and ask whether they are exercising agency or simply pretending they can control the outcome.
How do you think performing this show during a Fringe run will shape it?
The audience is effectively sitting at the table with me, so every performance will teach me something about when they trust the character, when they become suspicious of him and how long they are willing to enjoy the gambling before it becomes uncomfortable. A Fringe run will make the show tighter, stranger, and more honest.
Who do you hope this show finds at the Fringe?
Anyone who has ever believed that one job, relationship, investment or lucky break would finally make everything fall into place. I especially hope it finds people who have been praised for their persistence and are beginning to wonder whether they might need permission to stop.
I also hope it finds fellow degenerates and night owls. We don’t need to sit alone in the basement. Come be together.
Finally, if this show came with a warning label, what would it say?
Past performance is not indicative of future results.
Blackjack! (and other ways to get lucky) in Your Parents’ Basement runs at The Edinburgh Festival Fringe from 7th – 15th August 2026.