[Above: Cinnamon Bear with friend/captive (and future Portland Monthly editor-in-chief) Kelly Clarke at downtown Portland’s Frederick & Nelson department store in 1980]

A few years ago, my husband and I took our then-5-year-old son on the Cinnamon Bear cruise on the Portland Spirit. Memories of my own childhood holidays, spent listening to the old Cinnamon Bear radio show with my class at Southeast Portland’s Brooklyn Elementary in the early 1980s, came flooding back as we floated down the Willamette. I spent the entire cruise in a state of intense sentimentality (and a little bit drunk—mercifully, there’s a full bar on the boat).

Teary-eyed and triggered, I tried to convey to the hapless 20-somethings working the cruise—dressed as friendly pirates, queens, and, yes, a giant bear—how special my memories of Cinnamon Bear were, but I’m pretty sure I just came off as unhinged. My husband, who did not grow up in Oregon, was baffled at how emotional I became over this corny experience, and resorted to just handing me cup after plastic cup of Cook’s and Sunny D. You see, the Cinnamon Bear and I (and Portland, really) go way back.

The Cinnamon Bear is actually one of the longest continuously running radio shows in American history—Benson High School’s KBPS-AM (1450 kHz) still plays it during the holiday season, making Portland’s airwaves one of the show’s longest-running homes.

And the live-action version of the bear you love—or love to hate, with his dead, obsidian-black button eyes—was created right here in Portland. Generations of local kids visited the charming/terrifying giant teddy in lieu of Santa each holiday season between the 1940s and 1990s. Even today, our city is one of the last strongholds in America for this curious radio star turned department store mascot turned cruise ambassador. We just can’t quit him.

Let’s back up. In the dark days before the advent of television, let alone streaming media, families gathered around the radio for nightly entertainment. In the 1930s, the Golden Age of Radio, nationally broadcast serial shows were at their prime. There was Dick Tracy and The Lone Ranger, and, in 1937, American children were introduced to a furry Irish bear named Paddy O’Cinnamon—Santa’s “right-hand man.” 

Like many Portlanders, the Cinnamon Bear was born in California. He was created by radio program writer and director Glanville Heisch as the hook for a serial children’s Christmas program. Lured by the promise of easy sponsorship money, Heisch and his wife, Elisabeth, scratched the show out—story, songs, and all—in just six weeks.

The radio writer was told by producers to just riff on Alice in Wonderland or The Wizard of Oz and to make sure each of the 26 episodes ended in a cliffhanger. (See Episode 6: “Frustrated by a Pelican.”) And the story got pretty damn trippy, fast. The Heisches created a Candylandesque world with Lollipop Mountains, a patchwork toy dragon for a villain, and a band of buccaneers sailing the Root Beer Ocean—soundtracked by loopy tunes like “Never Say Boo to a Crazy Quilt Dragon.”

The hero? A toy bear with an Irish accent who guides twins Judy and Jimmy on a quest for their missing Silver Star, necessary to top their Christmas tree.

It was a hit. Department stores around the nation sponsored the radio show. Portland, of course, took things up a notch. Local store Lipman, Wolfe & Company brought the popular bear to life as a holiday marketing gag in the 1940s, crafting a hulking bear suit children would grow to know and love—or fear.

Cinnamon Bear made his first appearance in Lipman’s (in the building that now houses Hotel Monaco) in 1944, to the chagrin of Meier & Frank, Lipman’s main competitor, located across the street. At Lipman’s, Cinnamon Bear hung out with Santa and passed out cinnamon cookies in his own image, to be eaten as some sort of communion. By the 1950s he was so popular they’d trot him out for fashion shows in the Multnomah Hotel. The store even tried to capitalize on him at Easter, casting him as a helper for the Easter Bunny. In the 1970s, the bear delivered tens of thousands of cookies between his store appearances and visits to Portland’s children’s hospital.

For Evan Roberts, a local winemaker whose grandfather William Roberts co-owned Lipman’s from 1956 to 1968, time with Cinnamon Bear was supernatural. “He was magical to me because, in my mind, he was a stuffed animal who had come to life. Santa was just a weird old guy with a big beard, kind of spooky, and wanted to know if you had been ‘good,’” Roberts explains. “Cinnamon Bear was cuddly and handed out bear cookies. How could you go wrong with that?” 

Decades before the Portland Spirit was a thing, the Cinnamon Bear was already being cruised. Our furry friend was known as “A Real Casanova”—a phenomenon reported in 1967 and 1973 by two 18-year-old guys hired to play the Cinnamon Bear at Lipman’s. Teen girls purportedly whispered their phone numbers in his ear. Locals were in thrall to his hirsute sex appeal.

“The girls really dig him,” Lipman bear-wearer Glenn Simon bragged to the Oregonian in 1973. “I get all sorts of women sitting in my lap.... Old Cinnamon is strictly a lover boy.”

Not all the girls dug Old Cinnamon, though. After Lipman’s was bought by department store Frederick & Nelson in 1979, they kept the character and trotted him out for another decade, to the abject terror of some Portland children.

“Oh my god, I fucking hated that bear,” recalls Nico Bella, owner of downtown’s Spellbound Flowers. “He looked like a Sleestak [from Land of the Lost] to me, and I was terrified of those. It was in a doorway and came waving and walking towards me, and I started yelling, ‘No, no, NO!’ and wailing. I ran out screaming.”

(In addition to the Sleestak resemblance, some versions of the 1980s-era Cinnamon Bear suit look rather disturbingly like a Furry in blackface.)

In 1990, Frederick & Nelson closed its last Oregon store, hammering another nail in Paddy O’Cinnamon’s coffin. That same year, Oregonian Marybeth Gessele wrote the book No More Cinnamon Bear Cookies, which explains death to children. Coincidence? You decide.

The storied bear’s newest resurrection—with a teeny sailor hat and soulful eyes—debuted on the Portland Spirit cruise in 2005. So far, the two-hour boat ride has hosted thousands of locals for cookies, treasure hunts, and cheap bubbly. (Cruises run November 30 through December 27 this year.)

Holiday traditions change, and our city evolves, but for legions of fans (and some emotional, day-drinking moms), the cult of the Cinnamon Bear is forever.