When the 17th Street High Heel Race returns for the 31st time this Tuesday, thousands will likely attend to watch participants book it for the approximate 0.1 mile from the corner of 17th and R NW to the finish line at JR’s in high heels and Halloween finery.

Most of them will trot along the course, soaking in the crowd’s attention and crossing the finish line at a leisurely pace. But for some, competition is even fiercer than the drag queen looks that they plan to serve.

Each year, there are a slew of racers gunning for first place, an honor that nets the winner assured bragging rights and potentially drink tickets. We spoke to the winners of the last five races about their tips for being at the top of the medal stand.

The finish line at the 17th Street High Heel Race in 2013. (Photo by Ted Eytan)

Inertia
Winner: 2012 and 2013

William Dennis says that he didn’t necessarily plan on trying to win when he first participated with friends in 2012.

As his drag persona Inertia, he was wearing, “a not-so-good looking fro blond wig with this cheetah print romper and horrible, horrible make-up.”

But his past experience as a college track and field runner kicked in quickly. “Once I got to the start line, I literally got chills,” he says. ” All I saw was competition to my left and right.”

Focusing his eyesight on the finish line, he was the first to cross it, though Inertia’s outfit didn’t survive: “That poor romper had fallen all the way to my waist.”

Still, despite not practicing running in heels, “It came pretty naturally. I get the question a lot —’Is it the same [to run in heels]?’ Of course it’s not the same.” One thing that helps, though, is that trained runners are encouraged to run toe-to-heel, which helps with three additional inches on one’s heels.

The second year he participated, he says competition had ramped up because “more and more of the guys that I see on a regular basis and that I compete with at kickball and dodgeball started competing.”

He scored a two-peat wearing an outfit he says made Inertia look like ABC’s Robin Roberts, and gold-sequined three-inch boots provided by race sponsor Pacers.

“There was a lot of attention for the third year because a lot of it was, ‘Will William win for a third year?'” he says. “I was mentally ready. I had a nice entourage—we all dressed up as Sailor Moon, it was epic—but people were out for blood. It showed in the picture at the starting line.”

Starting line positioning is key, he says, because it determines how much effort a person needs to put in at the outset. Dennis says that’s what held him from victory.

That year, he came in second. “That third year kinda sucked—I hung up my heels.” Dennis has since moved to Atlanta, where Inertia has yet to make an appearance, but he toys with the idea of coming back for another High Heel Race. “My time will come again,” Dennis says. “Inertia will come back through.”

Tran Hathaway is second from the right. (Photo courtesy of Scott Teribury)

Tran Hathaway
Winner: 2014

Scott Teribury says that, from the first time he watched the High Heel Race, “I was like, ‘I’m ready to compete.'”

He found the name “Tran Hathaway” online and decided to wear “a Britney Spears school girl outfit, it was very scandalous, and some black boot heels” for the 2014 race.

“I got the heels and tried to practice by my house the day or two before,” Teribury says. “In high school and college I actually ran track and field and cross country, and running in heels is similar to running in track spikes.”

He says he used the same tactics he learned in track and field to navigate the crowded start. “The race is crazy—you have to get a good spot. When the gun goes off everyone is pushing and shoving.”

Teribury says the experience of crossing the finish line first is “kind of crazy: people surround you and are yelling. You don’t know what to do.”

He hasn’t been able to participate again since he won, due to a mix of injuries and travel, but is competing again this year. He hopes to repeat his 2014 performance, though he plans on coming up with a different drag name.

Tasha Salad. (Photo courtesy of Brandon Warner)

Tasha Salad
Winner: 2015

Brandon Warner came up with the drag name Tasha Salad at the McDonalds drive-through.

“I was never one of the walkers,” says Warner, who had never run in heels before participating in his first High Heel Race. “I always got there and I’ve always sprinted.” But despite giving it his all—in 2014 he actually lost a heel during the race—it took him a couple years of competition before he netted the victory, dressed as one of the girls from Taylor Swift’s “Bad Blood” video.

“The first year I thought I had it in the bag,” he says. “The nerves start to kick in when you’re there. You know what you’re capable of, but it’s D.C. You never know who’s going to surprise you.”

He says the experience of running in the race is “almost like an autopilot kind of sensation … You just go once they fire the gun.”

Warner says he didn’t brag too much about his victory, because he didn’t have to. “I’d go places and people would be like, ‘Oh you won the High Heel Race.'” An injury is keeping Tasha Salad from the competition. “This’ll be my first year watching the High Heel Race, not participating, since I found out about it,” Warner says.

Big Pharma after winning the High Heel Race. (Photo courtesy of Craig Williams)

Big Pharma
Winner: 2008, 2011, 2016

Craig Williams won the High Heel Race the first time he ever ran it, back in 2008, and has been “doing it pretty much every year since,” he says.

He’s the reigning champion, having won last year as Big Pharma. “I had on this blue, it looked like Viagra blue, dress and I had this cotton fat suit underneath and then I did terrible make-up,” he describes. “The idea was a Quinceañera dress and a girl got into her mom’s makeup bag and has no idea what she’s doing.”

Williams agrees that to win, “you have to jockey for a good start. A good half of winning the race is the first couple seconds of the race, and then it’s having the stamina to keep up with the few people who made it out to the front.”

It’s worth the effort, though. “It’s fun in the moment right after you win it, where everyone mobs the street and everybody wants that picture with you.”

If he runs it again this year, he’ll do it as his new drag persona Peach Poussay. “I have a shaved head and it’s a little bit of a buzz there and I don’t wear a wig with Peach Poussay.” When he dressed as Poussay for the annual drag soccer game, “I had a big giant basket of peaches that I threw at people throughout the game.”

But he’s considering retiring from the race. “I’m 36 now—I’ve run it enough,” Williams says. I’m not sure I’m going in for the win this year. But last year I thought about about retiring, and then I ended up winning.”

The 17th Street High Heel Race happens on Tuesday, October 24 at 9 p.m., not 7 p.m. as earlier stated, though participants will begin parading their costumes at 7 p.m.