In tragic times, friends Sam Ewing and Hattie Wolfe found a way to make a difference

Headdress Ball holds a special place in Orlando’s glittering fall social season. Part Las Vegas and part La Cage, the splashy event attracts gays and straights—including some of the biggest movers and shakers in town—to share a gloriously unlikely evening of costumes, beefcake and drag. In 25 years Headdress Ball has raised millions for the Hope and Help Center, now Central Florida’s largest AIDS service organization.

Most know that Headdress is the creation of respected interior designer Sam Ewing and his dear friend and fellow designer, Hattie Wolfe. But few know the moving story of its inspiration.

It was 1987. Gay men were getting sick and dying, still inexplicably. And Ewing had just lost someone he loved very much.

Patrick Bryan was a 4th grade teacher at an Orlando elementary school. With a gentle manner and boyish good looks, his students must have adored him. He was just 27 years old when he died of AIDS.

Bryan knew he wouldn’t be allowed to teach once his illness became apparent. He quit his job and planned to hike around California before AIDS claimed him. He wanted no obituary. He didn’t want his kids or their parents to worry.

“He took up so little space in the world,” says Ewing.

But Bryan soon got too sick for hiking. He returned to Winter Park, where Ewing fed him, bathed him, cared for him and loved him until he slipped away. And then Ewing, who by then had several friends who’d tested positive for HIV, was left to cope.

“My grandmother always said that the biggest man will be on his knees, and that’s what I did… I prayed,” Ewing says. “I thought, ‘How do you make any sense of this… of something so bad?’”

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The death of his beloved friend, Patrick Bryan, fueled Sam Ewing’s 25-year involvement with the Hope and Help Center.

He looked for resources and learned of a small support group—The Hope and Help Center—that met at the Unitarian Church on Robinson St. Ewing tracked them down and asked what he could do. They told him they needed money to expand services, desperately.

As it happened, Ewing had planned dinner with Wolfe that same evening, and she immediately agreed to help. They got on the phone and raised $6,000 from friends. And when they delivered the funds, Hope and Help asked them to take charge of fundraising.

“We got back in the car, looked at each other and said, ‘What are we going to do?’” Ewing remembers. “A car wash isn’t going to cut it.”

When a florist and Hope and Help board member offered that he’d attended a floral headdress fundraiser in Los Angeles, Headdress Ball was born.

Tickets for ‘Night Blooming’—it didn’t become Headdress until 1992—were $15. Ewing and Wolfe “spray-painted the filth out of the Beacham Theatre” and tasked themselves with selling 100 tickets each. They pressured gay friends and straight clients, and stumbled onto a formula that continues to define Headdress.

“I think it broke a barrier,” says Wolfe. “The straight people who came knew everyone there. They just didn’t realize they were gay… and that they live in the same world.”

They also worried about personal ramifications.

“I figured everyone would assume I was doing it because I was sick, and that I’d lose business… you have to remember how scary AIDS was back then,” Ewing says. “The irony is that it’s the most worthwhile thing I’ve ever done.”

But that wasn’t their only concern in 1989. They asked drag performers—some more reliable than others—to serve as models because they could support larger headdresses. And the delicate floral creations had to be assembled at the last minute. There was no opportunity to test them.

“It was already a funky event,” laughs Wolfe. “And that uncertainty just added to the funkiness.”

Ewing asked the notoriously bawdy Miss P to emcee, and secured promises of good behavior. When she sashayed down the runway and dropped the F-bomb—three times in rapid succession—Ewing was mortified.

“Hattie and I both had jet black hair before that night,” he laughs.

But they’d hit on something: a magical event that was naughty by nature, but loving and generous in spirit. On the way out, patrons enthused about next year.

“Great,” Ewing told them. “But next year you’ll have to pay for your ticket.”

In fact, that first time out Ewing and Wolfe bought most of the tickets themselves and gave them away. They charged for drinks and auctioned off donated centerpieces. They even sold bromeliads out front. And they walked away with $5,000—enough so that Hope and Help could hire the irrepressible Chuck Hummer as its first executive director.

“Hattie and I had no idea this would still be going on 25 years later,” Ewing says.

“Or that there still wouldn’t be a cure,” Wolfe adds.

The second year they returned to the Beacham, and this time popular WFTV personality Burdette Bullock promoted the hell out of it. Bullock died in 1993, but by then Headdress was a black-tie event at a swank downtown hotel. Florist Lee James modeled his own sexy leather peacock creation that year, and when women flocked to stuff money in his crotch another Headdress tradition was born.

By the turn of the century, Greg Brown, Pamela Bolling and John Best were producing ever-more spectacular events, unlike anything seen in fundraising circles in even the biggest cities.

“You can’t believe what it takes to put on this show,” Ewing says. “If it weren’t for all the people that volunteer their time and talent, it would cost a lot more and make a lot less.”

In 25 years, the money raised by Headdress Ball has made an incalculable difference for thousands of Central Floridians impacted by HIV/AIDS.

“Every year when I sit in a back corner of the ballroom and realize what this has become, I tear up,” says Ewing. “I’m not a showman… I fell into it. I just wanted to do something for a friend that died.”

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