Sugar Plum
Gary
Sugar Plum Gary returns to Annex Theatre!
December 12 – December 24, 2026
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 he experienced the real Santa, an ancient and sinister creature more Lovecraft than Dickens. Asking simply, “Does anyone have a question about Christmas?,” Gary unfolds an evening of hilarious and twisted holiday glee that begins on the fateful night when Santa visited the Rankin Bass Home for Unfortunate Children, leaving Gary as the only survivor.
Join Seattle stand-up comedian, storyteller, and gentle weirdo Emmett Montgomery for a delightful and sometimes terrifying adventure that’s always a different show every night.
All performances will be live streamed. Sugar Plum Gary is appropriate for all ages, especially those who no longer believe in Santa, but who love Halloween.
Tickets starting at $15
Performances
Fri, December 12 at 7:00 p.m.
Sat, December 13 at 7:00 p.m.
Sun, December 14 at 3:00 p.m.
Thu, December 18 at 7:00 p.m.
Fri, December 19 at 7:00 p.m.
Fri, December 19 at 9:00 p.m.
Sat, December 20 at 7:00 p.m.
Sat, December 20 at 9:00 p.m.
Sun, December 21 at 3:00 p.m.
Wed, December 24 at 7:00 p.m. (Christmas Eve!)
All performances will be live streamed.
About the Artist
Sugar Plum Gary is presented by Seattle stand-up comedian, storyteller, and gentle weirdo, Emmett Montgomery. Known for creating opportunities for odd, fun times on Seattle stages for two decades, Emmett was in the top 100 of season nine of NBC’s Last Comic Standing, voted by the readers of Seattle Weekly as “Seattle’s Best Comedian” three times and declared by the Stranger “a undisputable genius of Seattle comedy.” Emmett currently runs the twice-monthly stand-up variety showcase, Joketellers Union, with cartoonist Brett Hamil at Clock-Out Lounge. He’s one of the hosts of the Seattle Moth Storyslam, travels the country performing stand-up, teaches story-telling and comedy workshops, and is quite possibly one of the Pacific Northwest’s best paper bag puppet makers.
While Emmett and Gary have never been seen in the same place at the same time, people have claimed they bear a striking resemblance.
Jubilee Women's Center Clothing Drive
Throughout the run of Sugar Plum Gary, Annex Theatre will collect donations for Jubilee Women's Center. Items requested include:
women's clothing of all sizes
cosmetics
and other cozy comforts.
Emmett Montgomery as Sugar Plum Gary at Annex Theatre, December 2025. Photos by Jody Bolt.