This December, Sugar Plum Gary will return to Annex Theatre for another round of joyfully twisted holiday storytelling and existential cheer. Equal parts comedy, confessional, and cosmic horror, Sugar Plum Gary transforms the magic of Christmas into something hilariously strange and beautifully unsettling.
Performances run December 12–24, 2025, with both in-person and live-stream options available. Tickets, available on Annex Theatre's website, are sliding scale starting at $15, with pay-what-you-can accessibility for all performances.
A gentle-hearted “Santanist,” Sugar Plum Gary is a bushy-bearded man in jolly footie pajamas who has been haunted by the Holiday Spirit ever since his fateful encounter with the real Santa, an ancient and eldritch creature more Lovecraft than Dickens.
Armed with only a microphone and far too much holiday trauma, Gary invites audiences to ask: “Does anyone have a question about Christmas?”
From there, the night unravels into an evening of bizarre, heartfelt hilarity. Each performance is unique, being part improvisational stand-up, part holiday special, and part group therapy session for anyone who's ever wondered what lurks in the shadow of the Christmas tree.
Sugar Plum Gary is the creation of Emmett Montgomery, a Seattle stand-up comedian, storyteller, and “gentle weirdo” known for crafting unforgettable experiences across local stages for over two decades.
A three-time Seattle Weekly “Best Comedian” and NBC's Last Comic Standing top-100 finalist, Emmett has been hailed by The Stranger as “an undisputable genius of Seattle comedy.” He also co-hosts the beloved Joketellers Union showcase at Clock-Out Lounge and the Seattle Moth StorySLAM, teaches storytelling and comedy workshops, and—if the rumors are true—makes some of the Pacific Northwest's finest paper bag puppets.
While Emmett Montgomery and Sugar Plum Gary have never been seen in the same place at the same time, some suspect their connection runs… mysteriously deep.
Videos
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