Jessie Moore Oleson has branched out from Cakespy.com to a Capitol Hill art gallery featuring her work, a blend of charming and fey populated by anthropomorphic baked goods, and the work of others.
photographed by John Lok
IN A CAPITOL HILL gallery about the size of a breadbox, a petite young woman sits by the window in her makeshift studio, daubing watercolors on Bristol board in one of her signature miniature works of art.
Sound sweet already?
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The artist is Jessie Moore Oleson, better known in some circles as “Cakespy.” Her work, a blend of charming and fey, is populated by anthropomorphic baked goods, chiefly a cupcake christened “Cuppie.” She writes regularly about sweets, from delving seriously into the history of apple pie to creating wacky recipes like “Cupcake-Stuffed Cupcakes” and “Cadbury Crème Eggs Benedict.”
Earlier this year, she and husband Danny Oleson bought the former Bluebottle Gallery and transformed it into the Cakespy shop, showcasing Oleson’s own artwork and crafts as well as that of others (currently hanging: an oil-on-wood representation of a crusty baguette).
Oleson knows how unlikely her collision of talents is.
Artwork. Writing. And . . . baked goods?
A New Jersey native, she displayed her gifts early, sending a story submission at age 12 to Stone Soup, the children’s magazine.
The editors wrote back, she recalled. The story was rejected. But could they publish the illustrations she had doodled on the envelope?
Oleson, daughter of children’s book illustrator Margie Moore, graduated from the Pratt Institute of Art before going into design work at stationary studios (foodies might also recognize her as an opening server at Crow). While working as “head of the magnet division” at Seattle-based Madison Park Greetings, she started wondering, “How on Earth do I combine all the things I love into one?”
While she mused, she began Cakespy.com in 2007, featuring her own drawings and essays and bakery reports, as well as dispatches from guest “Cake Gumshoes” from around the country. You can guess what happened next.
The blog quickly became the heart of her business, with sales from original artwork increasing enough to quit her day job. She became a regular guest writer on the national food site Serious Eats, and her commissions included painting cupcake-themed murals for bakeries in other states. She taught watercolors to kids at a cupcake festival in Oregon. She spoke at a small-business conference: “When it comes to marketing, never underestimate the value of a free cookie.”
This year, Bluebottle owners Matthew and Andrea Porter left the gallery. They said they’d love it to stay alive with new owners. And Oleson thought, “Wow. Maybe that could be the next step.”
Now she walks to work from her Central District home, her pug, Porkchop, snuffling faithfully by her side. (He got his name from the dog in the Nickelodeon show “Doug,” which Oleson credits for helping her learn to draw cartoons.)
Being part of the community — whether hanging artwork, ringing up cards and mugs or hosting Halloween-candy tastings and a “Cake vs. Pie” contest — has left a better taste in her mouth than working alone from home or selling her work through a large distributor. And the gallery does branch out beyond food, featuring indie art and crafts and rotating guests’ creations in the tiny showcase up a spiral staircase. If there’s a connecting theme in the artists she chooses to display, Oleson said, “food and whimsy seem to be the two factors that come up.”
Oleson’s own clever confections brings to mind Quentin Blake (who illustrated the likes of Roald Dahl’s “Revolting Recipes”) and Ludwig Bemelmans (writer and illustrator of the “Madeline” books). She credits the early line-drawn New Yorker cartoons as influences, as well as children’s books like “Goodnight Moon.” She loves the fearlessness of New York painter-muralist Keith Haring. And those are just the artistic influences: Food brings on a whole other list, including her favorite cookbook, “The Betty Crocker Cooky Book,” “classic, retro and with oddly tongue-in-cheek hidden bits in the write-ups.”
At the shop on one recent weekday, popular blogger Angie Dudley, “Bakerella,” had dropped in to say hello while in Seattle on a book tour. Soon after, a visitor from Boston — one of Oleson’s guest “gumshoes” — walked in, saying she was heading for Vancouver and couldn’t miss a chance to meet Oleson in person. They posed for pictures; they hugged. She thanked Oleson for brightening her life every day when she checks out the Cakespy site.
And that’s Oleson’s goal with all her diverse talents — to seek, as her tagline puts it, “sweetness in everyday life.”
Rebekah Denn is a Seattle freelance food writer and blogger. John Lok is a Seattle Times staff photographer.