Ray Tillotson outside the former downtown Portland location of Ray's Ragtime, circa 2016

“Good days and bad days. I’ve had a lot of really kind support, and Lisa’s been a rock, but no, it’s ... every day is a new story,” says Jeff Taylor, widower of Ray Tillotson, the founder and namesake of Ray’s Ragtime, an institution among Portland’s storied vintage and secondhand style hubs. Tillotson died October 2 at the age of 71, according to an Instagram post by Ray’s Ragtime owner Lisa Beyer. Taylor and Beyer helped Tillotson manage a diagnosis of achalasia, a stomach disorder that contributed to other health conditions.

A century of garments branch from racks at Ray’s Ragtime (4059 NE Sandy Blvd), reaching from floor to ceiling. Garments and accessories primarily come from the 1920s–’60s but stretch from the 1890s to the 1990s. Tillotson frequently greeted customers from the shop’s counter—a wood-and-glass case overhung by a beam, demurely branded "beauty bar"—where he had a sniper’s view of the front door in a forest of fashion. The counter is surrounded on all sides by a cacophony of color and textures, with jewelry stored under glass and wig heads providing cover. “There’s no Ray’s Ragtime without that counter,” Taylor says. 

Tillotson (right) behind the Ray's counter, with local actor Ross Huffman-Kerr, sometime in the 1980s

Tillotson, originally from Corvallis, founded Ray’s Ragtime in 1986. Ray’s Ragtime was a downtown Portland landmark for 30 years before being priced out by rent increases. “[Ray] was looking to pass the torch and relocate,” Beyer says. Beyer purchased the store when it moved from SW 10th and Morrison to the Hollywood District in 2016. Before she worked for them, Beyer met Tillotson through Taylor, whom she befriended during her time at Music Millennium. Tillotson could still be found regularly behind the counter after her succession. He had a well-established reputation for making longtime, first-time, and A-list customers alike feel accepted and understood. He was ready to regale visitors with riveting life stories and entertainment history at the drop of a hat.  

Ray Tillotson (left) and Jeff Taylor

“One thing that really touched me, and I know would touch Ray, too, that I heard after his passing from a variety of people, was how they felt that Ragtime was a safe space for so many people, that it was some of their first introduction to gay and lesbian culture, to antique culture, vintage culture,” Taylor says. “I can’t say we ever set out to, I mean that wasn’t the goal as far as that goes—we were two gay men trying to make a living—but I was really moved and touched by a lot of people’s comments, and I know Ray would be, too.”

“Overall he was a very fun and charismatic person to get to chat with,” Beyer tells Portland Monthly. “He engaged customers with fun, entertaining stories about various celebrities like Courtney Love and George Clooney and Laura Dern.” Portland State University magazine Pacific Sentinel notes Adele, Sean Ono Lennon, Florence Welch, and Faye Dunaway are among the legends who held space with Tillotson, while Beyer told FOX 12 last year that the rapper Yelawolf, the Dandy Warhols, Florence + the Machine keyboardist Isabella Summers, members of the Sun Ra Arkestra, and Hole cofounder Eric Erlandson have visited Ray’s Ragtime in Hollywood since the move from downtown Portland.

Taylor says Ragtime Ray’s early customers ran in Portland’s punk scene, fans of singers like Siouxsie Sioux and Poly Styrene. “It was a lot more hard-core back then,” he says. “Vintage was a counterculture thing at the time, and it was when Ray got into it. It’s an aesthetic that wasn’t necessarily mainstream ... it was very nonconforming, in a lot of ways, and I think that’s what attracted Ray to it. That, and he made good money from flea markets in college.”

Recently, COVID lockdown shifted vintage focus from formal wear to lounge and casual wear, but Beyer has noticed trends in 1940s style and statement pieces that reseller apps like Depop can’t predict. “With the popularity of The Queen’s Gambit, set in the ’60s, that set a resurgence for people looking for that look,” Beyer says. “Every era has its time of popularity, where it becomes the hip thing to wear or seek out in the vintage world.” 

While Ray’s Ragtime has also put more emphasis on online sales, Beyer still enjoys when customers shop in person. “We get a lot of customers that have never had any experience with the downtown store and don’t know what that was about,” Beyer says. “Primarily, when we get those new customers—maybe they moved here in the last couple of years, things like that—they’re just so excited to have found a place like this because they’re largely going extinct due to everything being so focused on online sales and online stores. Right now, it’s an anomaly that people are excited to experience and punch around a physical location and find that one special treasure that’s hiding around.” 

Taylor, an antiques enthusiast and movie memorabilia collector, met Tillotson behind a similar-such counter in 1994. They began their relationship in 1995, growing closer at the infamous gay bar Flossie’s, which begat the Old Town strip club Silverado. From there, they lived the life lonelyhearts dream of while Netflix-and-chilling. “I went over to his house one day, we watched movies and drank blackberry and soda,” Taylor says, “and basically, like Ray always used to say, ‘Jeff never went home.’ We were kind of married from then on.” (Taylor says he and Tillotson considered themselves married, but chose for personal reasons not to get a marriage license when same-sex marriage was recognized in Oregon in 2014.)

Tillotson was a local theater actor, performing in Fiddler on the Roof and Camelot for Portland Theater Company, Civic Theatre’s Scapino!, Storefront Theater’s The Storefront Burlesque, and various Shakespeare plays. He appears in the 1989 creature feature Tunnels (also known as Criminal Act), in which two journalists investigate reports of giant rats in New York sewers. “Ray would roll his eyes at that one, but he loved to talk about his projects,” Taylor said. 

Tillotson in full clown makeup (right) in a promotional image for The Storefront Burlesque

Beyer and Taylor share Tillotson’s legacy through Ray’s Ragtime, and through art. Along with a private memorial capped at 50 people, Taylor hosted a screening at the Hollywood Theatre in Tillotson’s honor, showing their favorite movie, the 1982 black comedy Eating Raoul. Beyer paid tribute to Tillotson with a swing music episode of her XRAY.fm show, Inside the Wizard’s Hat. While the collection cultivated and stewarded at Ray’s Ragtime is still an Old Portland treasure, Tillotson’s personal daily contributions are irreplaceable.

“He was an extremely good person, an extremely kind person. He was my husband and I miss him every minute,” Taylor says. "I’m sorry that a lot of younger people won’t get a chance to meet him and get to experience him and his humor.”

A GoFundMe campaign organized by Lisa Beyer is accepting donations to pay for Ray Tillotson’s medical expenses.