Conversation on Drag: Dear Ruthie and Gary Olson

A drag queen and the manager of Hamburger Mary’s chat about the state of drag.

Something for Everyone

Dear Ruthie, drag queen
Gary Olson, manager, Hamburger Mary’s

Drag’s been around for centuries. But it’s really taken off in the last 10 or 20 years, as queer culture has gained more mainstream visibility and queens like RuPaul have helped popularize the art form. We sat down with Dear Ruthie, one of Milwaukee’s most established queens, and Gary Olson, who manages Hamburger Mary’s, to chat about the current state of drag in the city.  – Moderated by Lindsey Anderson

This conversation was published in the January 2019 issue of Milwaukee Magazine’s cover story: Let’s Talk It Out.

Something for Everyone: Dear Ruthie and Gary Olson

DR: The drag scene in Milwaukee really has exploded. And I think that Hamburger Mary’s has had a lot to do with that, because once they moved into Milwaukee, our drag shows got bigger and bigger. You started seeing more straight restaurants having drag shows and straight bars having charity drag shows. And it’s a really exciting scene because drag is expanding so quickly. Now we have bearded queens and goth girls, and it’s just expanding into such a different realm now. You can find whatever kind of drag you like in Milwaukee. And that is really on par with Chicago.

GO: I think so too. The diversity of the casts is incredible, too. Sometimes, girls come from out of town and they don’t realize what kind of crowd we get in here.

DR: And, whether you like it or not, “RuPaul’s Drag Race” was a game-changer. It brought drag into people’s homes. It also made the queens up our games. And I also think drag, partially because of that show, has almost become a rite of passage for a lot of young people. Almost every young person you talk to will say, “Yes, I did drag once. Yes, I performed here once.” Whereas in the past it was like, “I did it for a Halloween party,” maybe.

GO: I did it once. Never again. I looked like my aunt, and I don’t like her.

DR: It wasn’t bad.

GO: It helped me appreciate what these divas do to perform. Some of them are performing three and four nights a week. I give them a lot of credit, because there’s a lot of money involved.

DR: Oh, it’s very expensive.

GO: I see what they have to spend on makeup, on outfits, on boots …

DR: Hair.

GO: Hips.

DR: For a good percentage of us, we are entertainers. So we love doing it. I love doing my little comedy stuff before a show. I love emceeing a show.

We did have a couple here once, they came in for the drag show, and they thought it had to do with drag racing, with cars. And they kept asking you about it. You were like, “Well, we do it right here.” And they were like, how do you – ?

GO: How do you get the cars in here?

DR: And you’re like, “No, it’s a drag show, where men dress like women.” They were like, “Wha-a-at?”

GO: They did not see the performance.

DR: I think my favorite thing, though, is when senior citizens come. I love that. Because they are from a different era, and so it’s nice to see an older lady or gentleman just laughing and clapping and dancing. And when they come up to us after a show they want to touch our hands and just thank us for the night. It’s fabulous.

GO: We had that experience in here three or four weeks ago. A tour bus of older women came just for the show. They wanted to touch the queens’ hands, their hair, their boobs, and say “How do you do this?!”

DR: I’m touched a lot.

GO: I agree. She is touched.

DR: In more ways than one.

“Let’s Talk it Out” appears in the January 2019 issue of Milwaukee Magazine.

Buy a copy at or find the January issue on newsstands, starting Dec. 31.

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