Performers at Chicago's Best Worst Drag Show Credit: courtesy Alben Dauti Alper

Like a gayer, more magical Brigadoon, every Monday night—the wee hours of Tuesday, technically—Chicago’s drag community, closing-shift bartenders, and after-afterparty seekers congregate for one of the best queer celebrations in the city. For the past ten or so years, the Jackhammer Complex in Rogers Park on the city’s far north side (6406 N. Clark) has hosted the lovingly titled “Chicago’s Best Worst Drag Show” at the beginning of each week from 2 to 4 AM.

Publicizing a sanctuary for LGBTQ nightlife-industry folks who are looking to unwind might normally be considered gauche, but the more-the-merrier, come-as-you-are vibe in the air at “Best Worst” has been part of its attraction since its inception. Delmar Medina, who created the show with another bartender at the time, “would bring in wigs, shoes . . . there were like four, five racks,” says Arben Dauti, who has hosted “Best Worst” for the past seven years. “He would go around and be like, ‘Hey, do you want to do a number?’ So these weren’t really performers in the beginning. And then people got wind of it. Slowly but surely, we became like one of the longest-running [drag competitions].”

Arben Dauti, host of Chicago's Best Worst Drag Show
Arben Dauti, host of Chicago’s Best Worst Drag ShowCredit: courtesy Arben Dauti

Brendon Lawrence, who performs as Kennedy and hosts Jackhammer’s American Horror Story viewing party on Wednesdays, recalls a similar origin story. “The bartenders and the regulars would get wasted and get into really quick, crappy drag,” Lawrence says with a laugh.

“Best Worst” has long outgrown its days of having to solicit bystanders to take the floor wearing what queen Shalita Cake refers to as “Delmar’s drag droppings,” but a point of pride for the show is that the bar for entry hasn’t gotten much higher.

Alongside prime-time amateur nights like T Rex’s “Crash Landing” at Berlin and Frida Lay’s “Drag Race” at Roscoe’s, “Best Worst” is one of the sign-up gigs that gives new queens the opportunity to brush shoulders with more established names in a supportive, risk-encouraging environment. And for veterans of RuPaul’s Drag Race, it’s a popular destination to mingle with the audience and watch colleagues. “They just like to come and be incognito,” says Dauti.

Monica Beverly Hillz, who directs the late-night show “Babes in Boyland” at Jackhammer on Thursdays, discovered Jackhammer’s late-late scene at the suggestion of one of her girlfriends shortly after her run on the fifth season of RuPaul’s Drag Race. It felt like an epiphany. “You know me,” says Hillz. “I like to make money, I like to have fun, and I like to go to new places, so we went to Jackhammer, and I absolutely fell in love with it. . . . I felt like it was probably one of the best shows I saw in a long time.”

More so than, say, at the notorious Lakeview IHOP (affectionately and unofficially dubbed “GayHop”) at 2 AM, the interactions at “Best Worst” are more digestible for recognizable queens after a long night. “After being on Drag Race,” says Hillz, “I have to be choosy where I go at this time of the morning. You’re going to be taking pictures with people. People are drunk. People are going to be really in their feelings, and it’s going to be too much at that time.”

Something else she noticed: the attentiveness and engagement of the crowd. For queens, the popularity of “Best Worst” among both queer and straight industry workers means a disproportionately chill audience of good tippers who by and large can handle their booze. And for the post-2 AM bar hoppers who aren’t effectively handling their booze, “Best Worst,” like many drag shows, endures as one of the surviving outlets for roast humor. “I told [Dauti] he reminded me of Joan Rivers in a Paul Bunyan costume,” says Lawrence.

For Dauti, reads—witty burns delivered by drag queens—are both a lighthearted feature of the show and an effective tool for checking spectators in the audience who are pulling focus from performers or, worse, invading their personal space. “If somebody gets a little bit too touchy-feely with the girls or, you know, is bothering someone who is performing, then I’ll say something,” he says.

Credit: courtesy Alben Dauti Alper

Up a few stairs from the main stage, the dozen or so performing queens set up a row of mirrors on the upstairs bars which becomes a makeshift dressing room, a better lit, calmer, unofficial staging area for queens to give each other pointers and grab a bite (in recent weeks, food has been provided by sponsor and next-door neighbor Leather64Ten). As Shalita Cake, who works the door for “Best Worst,” puts it, “We literally break bread together.” While she doesn’t want to give the impression that all drag queens are starving artists, the reality for many of the girls who compete is that they’ll have spent their last dollar for the week on that night’s look, then use tip cash to get home, so a hot bite at three in the morning goes a long way.

And for audiences looking to take a respite from the crowd on the main floor—or, as Dauti jokes, for spectators who’d rather “put on a show”—the bathhouse-y, sex-positive downstairs bar referred to as the Hole is open throughout the night. After the closure of Man’s Country last year, the Hole, and the back room at Touche next door, and Banana Video in Andersonville remain as the few old-school cruising spots north of Uptown, something that surprises newbies.

“I bring [guys I’m dating] to the Hole,” says Hillz, “and they’re just like, ‘Whoa, I never knew stuff like this even existed, let alone in Chicago.'”

But as Shalita Cake notes, the Hole is a spot where everyone can celebrate who they are—especially on Fridays, when the dress code mandates shirtlessness. “We’ve had trans men, women, everybody in between, wear their first harness and feel a little freer,” she says. “I’ve seen it help so many people with their body issues . . . everyone is welcome there.”

During “Best Worst” on Mondays, though, most folks stay upstairs for the duration of the competition. Over the past decade, Alper has observed that crowd has grown as RuPaul’s Drag Race found mainstream viewership. “In the beginning, it wasn’t as busy. Drag back then wasn’t as popular. It was like season-one RuPaul, and it was our season one too.”

And as details trickle out about the upcoming Drag Race All Stars season four, it’s worth remembering an observation former contestant Kim Chi made on Twitter last year: “If you can name every single drag race queen but can’t name ten local queens in your hometown, you’re a drag race fan, not a drag fan.” Luckily for Chicagoans, there’s no shortage here of opportunities to see fabulous queens do their thing live—no matter how late it gets.   v