She sings “I Will Always Love You.” Not lip syncs. Sings.
She sneaks behind the middle linebacker and pulls down a touchdown pass.
She lists her most recent job as “Meat Rack Monitor at the Fire Island Pines.”
When god made Jackie Dupree, he made only one.
The New York drag queen known for belting out hits over the mic has been performing in drag for over 20 years.
She’s also been playing in the New York Gay Football League for almost as long. A player in the league’s first season, defenses largely ignored her when she entered the league, probably because she was a drag queen. To their own peril. With hands the size of South Dakota, she could catch balls like nobody’s business.
That’s helped her teams to win three league championships over the years, a record for drag queens in New York City.
“I’ve gotten competitive now,” Jackee said recently from her home in Manhattan, “almost where I’ll spit on my hands and rub ‘em together when I know it’s getting serious in a game.”
Jackie got recruited by one of the league’s founders, Tim Hughes, who spotted her at one of her Manhattan performances at Barracuda and noticed her large hands. He knew that equated to catches and touchdowns, so he asked her to join the football league in 2005.
“I thought, who’d want to join that,” Jackie remembered, “it’ll be a bunch of guys not wanting to get hurt.”
It was anything but. Jackie quickly met former college and high school football players, as well as a bunch of other weekend warriors looking to fight for a win. She was hooked. She missed a couple seasons since then, but she’s been a staple of the league.
Before she created the Ms. Jacqueline Dupree persona, she was just James Cole, a Michigander who grew up in Detroit. A new gay friend led her to move to Philadelphia in the late Nineties, where she first dabbled in drag.
“I was always singing women’s songs,” Jackie said, “so I dressed up in drag one night and won $200 at a competition.”
She was hooked and an instant sensation. Before long she found herself in New York City, hosting karaoke nights and singing at places like Splash (may she rest in peace), Esquelita and the historic Stonewall Inn.
Before the pandemic shut-down, Dupree was doing one show a week — Friday nights Bottoms up at Vodka and Soda — but had a couple more in the works. She’d been hoping to return to Fire Island to perform this summer. Now she’s not so sure.
“That’s my spot,” she said. “If you go to Cherry Grove, people don’t care who you are, black, white, tall, gay, lesbian. Cherry Grove is where it’s at. That’s where the parties are.”
Cherry Grove and The Pines have been the two LGBTQ towns on Fire Island for the last few decades.
Now an international recording artist, and having performed at two Gay Super Bowls, Jackie laments missing the spring football season with all of her friends in the football league. But she knows she’ll be back and bigger than ever.