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The Silly William Gambit

Written By & Starring Matt Bader

He’s not playing chess against Death. He’s playing against something far worse...

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Silly William is an eccentric chess prodigy who finds himself trapped on a train bound for Hell (or Philadelphia, as it is known in some circles). And he finds his only company on the train to be a mysterious entity named Bum Fiddler, who challenges Silly William to a series of chess matches; wagering Silly William’s life against the chance to ride the train to wherever he wants to go. And oh, the places they go. Narrated in real time by the titular Silly William, they play seven chess games on a chessboard projection in the center of the stage, so that every line of dialogue is attached to a move on the board. And both characters are portrayed simultaneously by the show’s author and star, Matt Bader. As Silly William takes you into the minds of the two players and witfully explains the logic behind their moves, he additionally regales the audience with tales of a place called Colorado, a chess playing dog named Cynic, the invention of Bandroom Baseball, and many more memories from his youth. (Queen’s Gambit meets Lemony Snickett’s: A Series of Unfortunate Events). But as his memories begin to intertwine with the reality of the game in front of him, Silly William becomes forced to unravel his past and confront the grief he still harbors from the loss of his best friend, Bandroom Dinger, who brought light to each of those memories. The stakes are raised even further when Silly William uncovers that the chess-playing entity across from him is none other than addiction itself; the addiction that claimed the life of his best friend and which now consumes him.  In the final act, Silly William will have to put his gambit to the ultimate test as the line between Silly William and Bum Fiddler begins to blur– in the one man show that asks where one man ends and the addiction controlling him begins.

The Journey & What's Next

The Silly William Gambit had a successful run at The Edinburgh Fringe 2025, directly followed by a sold out limited engagement at The Producers Club Theatre NYC. We are proud to announce our next run as one of the Manifestival Mainstage shows at Paradise Factory Theatre in July of 2026.

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The Wee Review  ⭐⭐⭐⭐:
“​​Each of the places they (our protagonist and his nemesis) visit is fantastical and absurd, yet rooted in a reality we can recognise….Actor-playwright Matt Bader evokes each location with a deft comic touch, flipping between roles and narrating the detail of the scene, deploying a kind of delirious but measured energy which keeps the train on its tracks and chugging happily along.” 
“You dont have to know chess to follow the story line… an audience which appreciates both chess and wacky theatre may not be that easy to find. If you’re in that segment of life’s Venn diagram, though, you absolutely shouldn’t miss this show.” 

Fringe Review: 

 

“It’s a technically challenging offering which is well performed.”

“Bader makes the stage very much his own and is adept at leaping from one side to the other, giving the words physical force and focus. It thoroughly enhances the production.”

©2026 DMI

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