Montgomery on stage, surely thinking about his Secret Grandpa responsibilities

Creepy grandpas, chihuahua ice cream cones, and spatulas with insect legs.

These are the things that Emmett Montgomery is thinking about when he wakes up in the morning.

A self-proclaimed weirdo, Montgomery has been a standup comedian, storyteller, and artist on Capitol Hill for years. Recently he unveiled his latest creation — the Secret Grandpa Subscription Service.

“This was kind of a wonderful experiment,” he said. “Now it’s a significant part of my day. I wake up thinking about what weird grandpa thing I’m gonna do.”

Montgomery, who is on stage as a comedian and storyteller nearly every night in venues across Seattle, started the Secret Grandpa Subscription Service after he came up with a joke too dirty to tell on stage. So he offered to sell it to his Facebook friends for $2 as a fun experiment.

Inspired, Montgomery drew a “scary mustache grandpa” and offered to add a personalize the message and send it to people for $3. He was surprised by the interest and set up on Patreon. The rest is grandpa history.

“I think the only way we can have strange and wonderful and dumb and meaningful things in our lives is if we participate and support them,” Montgomery’s writes. “When people give money to creators they are buying them sandwiches and helping them pay for their antidepressants and letting them know that the things they do matter and good enough to have in their lives.”

The Secret Grandpa service is as simple as a personalized message on of one of his many mustache grandpa drawings. Montgomery’s other artwork includes drawings of his now famous 12-year-old chihuahua, Donna, and seemingly random objects—a spatula, an ice cream cone, a can of La Croix—with insect legs attached to them. His creations, it seems, have garnered a small, weird following.

“I’m really into building community with weird ideas,” he said. “Seattle has always been a place of neat, strange, and beautiful things.”

Montgomery lives in an apartment on Capitol Hill with Donna and Kate, his wife of nine years. A professional standup comedian, he likes to do things that “create community and explore imagination.” In addition to his comedy, he performs as “Sugar Plum Gary,” a drama persona that delves into the darker side of Christmas joy. He’s also the host and producer of the variety show Weird and Awesome with Emmett Montgomery, the standup showcase Joketeller’s Union and The Magic Hat, a basement show.

During this interview with CHS, Montgomery said he was in the process of trying to become friends with crows, but he would soon have to leave to record a podcast.

“I like this city and I see its challenges. I feel really powerless in it. All I can do is interact with its people. I try to be a positive part of the people,” Montgomery said. “Seattle is a great city to not fit in. I’m never not going to be a weirdo.”

You can learn more about Emmett Montgomery and join the Secret Grandpa Subscription Service at patreon.com/spidergrandpa.

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