Interview with Illustrator Jessie Oleson

Seeking sweetness in everyday life, this Seattle artist is the creative force behind many of the illustrations in Taste of Home. Just don't tell her friend Cuppie!

Jessie Oleson and Cuppie

Jessie Oleson and Cuppie

Mom is a children's book illustrator and dad is a watercolorist; so it is no surprise that Jessie Oleson has had crayon in hand from a very young age. A student of the Pratt Institute in Brooklyn, Jessie has worked a hodgepodge of artistic jobs from drawing greeting cards in New York City to being the art director for a refrigerator magnet company in Seattle.

Now self-employed and drawing freelance fulltime, she also devotes a lot of her time to her blog,, a product of her lifetime love for baked goods and search for sweetness (and sweets) in everyday life. Jessie and her fellow 'spies' write about and review bakeries and sweet treats all over the country, all with the help of Cuppie, her creative muse and, if you ask him, the real star of the show.

Follower's of have seen Cuppie and his anthropomorphic food friends in an array of humorous situations. They have been spotted dancing at a local disco; have gotten a little rough and tumble in a roller derby match. He makes the world a safer place as a super hero and has even gotten involved in a little crime scene investigating. But most of all, Cuppie has been the visual voice of many a piece of cake or delicious cookie.

As if all that talent were not enough, Jessie is also an accomplished writer whose sweet stories and interviews have been featured on the Seattle Post Intelligencer website and Recently, she even interviewed a pair of bakers from Brooklyn using her illustrations, with Cuppie's help of course, to ask the pressing questions that plague today's bakery fans.

Jessie has been drawing for Taste of Home for about a year now. Her "Starchy & Husk," refrigerator Olympics and cafeteria food antics are just a few of the scenes that have graced our pages. Today, Jessie is responsible for the art behind the TOH Kids in the Kitchen coloring book pages.

Interview with Jessie and Cuppie


Taste of Home: When did you first realize your love for illustration and what is your background, your inspiration?

Jessie: I've been drawing little characters and illustrations as long as I can recall—I have baby photos of me with crayons to prove it! I give my parents full credit for this, of course—my father is a skilled watercolorist and my mother is a children's book illustrator. My love of drawing cute characters, though, developed out of the cartoon shows and children's books and magazines of my childhood: I would try to emulate the styles and characters I loved, which eventually gave way to creating my own cute characters!

Jessie, where did you and Cuppie first meet?

Jessie: It was on my birthday! When it comes to birthday cake, my preference is very specific: a three-tier vanilla layer cake with pink buttercream frosting! As you can imagine, such a cake requires quite a bit of time and preparation, so in general it's a good idea to make extra cupcakes using the extra cake batter and frosting so that everyone can have a sweet to tide them over and prevent possible riots until the cake is served. It was one of these little extra cupcakes, with a jaunty cherry on top, that caught my eye…
Cuppie: She tried to eat me!
Jessie: Oh Cuppie. You know I'd never eat you… (stomach rumbles)


What is the oddest request you have received for illustration?

Jessie: Actually, I would have to say that Taste of Home takes the cake on that one—doing an illustration of an uncooked Thanksgiving turkey being chased by a hairdryer and leaving a trail of veggies in its path was a pretty funny request! Sometimes the unusual requests are the most fun to create though!
Cuppie: Well, since I wasn't even in that illustration (glares), I'd have to go with the one she did of me and my cupcake friends at a swim meet. I mean, cupcakes and chlorine? Blech!

This is your first time visiting Taste of Home. What are your impressions?

Jessie: I had pictured Taste of Home as a sort of foodie fairyland, complete with food experimentation, fashionplate photo shoots (but with food instead of models), and creative types running around with platters of cookies and foods. And you know what—it lived up to my expectations! There was so much activity, enthusiasm and excitement going on—forget that dream of being locked in a candy store overnight, I wanna be stuck here!
Cuppie: I really enjoyed Taste of Home—all those friendly people! Several people said they'd love to have me for lunch, isn't that sweet of them to invite me?

pea pods

TOH is a different avenue for your work. What has been your favorite part about working with TOH?

Jessie: The people for sure! Everyone I've worked with is just a powerhouse of creativity, and so wonderful to work with!

Tell us about your life online.

Jessie: Well, I run a website called, which is a "dessert detective agency"—where friends, family and I write about the best baked goods, recipes, products and services related to sweets that we've "spied!" Cuppie is the site's mascot.
Cuppie: I know that they write about something on the site, but I'm the real reason people visit—I mean, you can't turn off good looks like these!

What does the future hold for you and Cuppie?

Jessie: I guess we'll see! If someone had told me five years ago that I would be making a living drawing anthropomorphic foods, I probably would have laughed at them, but here I am! If I'm given license to dream big, I'd say that one day I'd love to make Cuppie into a cartoon like the ones that inspired me to become an artist when I was younger!


Find more of Jessie's work in our Kids in the Kitchen coloring book.