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Ruby James Knight, an Iowa drag legend for 30 years, passed away late Thursday after taking on all kinds of challenges stemming from stomach caoncer.  Jim Raymond, who played Ruby James Knight, took time about two months ago, before his illness took another severe turn to talk with The Real Mainstream about his career, and how he credits Ruby James Knight, her style and generosity, and her fellow queens with transforming his life.

WATERLOO — With her classic Phyllis Diller outfits, retro wigs and dignified demeanor, Ruby James Knight is a 30-year fixture of Iowa’s drag scene.

But she didn’t get there on purpose: Ruby James Knight is the stage name/alter ego of Jim Raymond, who was hanging out at a bar called The Bar in 1995 with a group of his co-workers at John Deere Co.

He and his friends took the stage in drag, “for fun,” Raymond remembers. But it became more: Raymond caught the eye of Courtney Michaels, a house queen at the time and still a veteran performer statewide, and Lili Whyte, another revered queen from Des Moines.

Michaels invited Raymond back to the stage and helped him get started on doing his own make-up and clothes. A few stage names and years later, Ruby James Knight was born.

She went on to earn the title of Miss Waterloo in 1998 and 2008; perform at the former Kings and Queens and nationwide; mentor other drag performers; help start the tradition of “drag wars” among Iowa’s LGBTQ bars; perform on-stage at Cedar Valley Pride Fest for 11 years; and help Waterloo become a more welcoming place for LGBTQ people.


Jim Raymond’s transformation into Ruby James Knight came later in life

Raymond, 68, said that for much of his life, he’d felt anxious and detached. “I was always such a shy person,” Raymond said, who remembers first experimenting with drag as a fourth-grader, for a Cub Scouts play. “I hated school, and I hated book reports.”

But the night Raymond took the stage with his co-workers, Michaels remembers Raymond’s “passion.”

“He seemed to have the passion for it and loved being on stage,” recalls Curtis Dietz, who performs as Michaels. “I think it started his Drag Journey. Ruby always said, if you have any complaints about his drag. ‘blame Courtney because she got me started doing it.’ ”

The ability to step outside of himself and dress up is a boost Raymond says he’s never found anywhere else. “When you’re in drag, you’re a whole different person. You have all these people looking at you, and you’re doing your thing and dancing and lip-syncing. And you kind of get their whole world. It gives you incentive to keep on going. Through the experience of being Ruby James Knight, I gained confidence in myself.”

Knight’s self-described style is “classy”

As a performer, Knight is known to be generous and charismatic. “From the first moment, I noticed (Ruby’s) stage presence, talent, and the overall will to give,” says Whyte, who is Greg Ross in real life.

Knight describes her own style in traditional terms. “I like to dress pretty. Sequins, gowns, pretty dresses,” Knight says. “I’m not into the  showing skin, boobs and all that stuff. I like to keep it classy, like something that, when you dress up for church or whatever, you always put on your finest.”

And while Knight says she’s “not a fan” of the gender-fluid style of drag featuring “beards and moustaches while you also have boobs and stuff,” Knight  encourages every drag performer to be themselves regardless of others’ tastes. “That’s my own personal feelings. To each their own.”


Ruby turned out in March to be honored despite health problems

When this article first ran, Raymond had been on the upswing following chemotherapy for stomach cancer. He was rebuilding strength in his legs after tubes he needed while in the hospital damaged his throat and made it hard to eat. His tumors were shrinking.

But about three weeks ago, says Ross, Raymond became severely ill again. Doctors discovered he had a bone marrow deficiency, and the chemotherapy had been slowly poisoning him. Doctors had decided to temporarily stop chemotherapy until Raymond grew stronger, but after only a few weeks the tumors had returned triple their size, Ross said, pressing on vital organs and interfering with everyday functions.

Raymond was hospitalized Friday, Ross said. He said his friend is partly conscious and pain-free because of medication, but unable to speak. Ross and many others have been offering tributes already, and Ross says he has found a comforting way to regard Raymond’s passing should it happen soon. “We’ll just have another  guardian angel. That’s one of the easiest ways to think of all of this. He’ll be up there keeping an eye on us, and probably cursing us out, too.”

Raymond also turned out as Ruby James Knight in March for a celebration in the drag queen’s honor, and performed for the first time in six months. Knight was also featured in a 2020 video by Experience Waterloo, in which she talked about how drag audiences have changed over the years – from mostly LGBTQ people, to a lot more straight people.

“Now you look across the crowd, and it’s a good mix. That’s a good thing. That shows acceptance of what we do and who we are.”

This article first appeared in the April/May edition of The Real Mainstream available at libraries throughout Iowa and Illinois. You can ask for those locations, or request a copy, by emailing Photos courtesy of Jim Raymond, aka Ruby James Knight.