Benefiting the Hope and Help Center of Central Florida

Saturday, September 20

Hilton Orlando

The Hope and Help Center of Central Florida is one of the largest HIV/AIDS service organizations in the state of Florida, and is the main provider of HIV testing, education, and other programs for the Orlando metro area, including Orange, Seminole, Lake and Osceola Counties.

Their signature fundraiser is the Headdress Ball, which will celebrate its 25th anniversary this year. The glamorous black-tie gala is one of the must-attend events on the Orlando social calendar each year, and this year might just outdo all previous years! It will be held at the Hilton Orlando (6001 Destination Parkway) on Saturday, September 20, starting at 5:30.

This year’s event includes a dinner, a silent and live auction, and a special choreographed show highlighting the history of the Headdress Ball through video, voiceovers, and of course headdresses. Over $500,000 was raised during the fundraising portions of the Headdress Ball last year and Hope and Help hopes to surpass that amount this year. The money raised from last year’s gala helped Hope and Help continue to serve over 4,600 people across the Orlando metropolitan area.

Special guests Chad Michaels, well-known for her Cher impersonations and for winning RuPaul’s Drag Race: All-Stars, will open the show, and pop star and former “teen queen” Debbie Gibson will close it. JMBest Entertainment and Hardrive Productions will produce the shows seen during the Headdress Ball.

Tickets are available now, but they are selling out fast. They can be purchased by going to and clicking “Tickets,” or by calling (407) 645-2577. Due to high demand, VIP packages are no longer available. Individual tickets are priced at $300 each and a silver-level donor table (including dinner and the main show) costs $2500 and seats ten guests.

I talked to Christopher Hessler, Hope and Help Events Manager, about the Headdress Ball and how excited he is to celebrate 25 years of the iconic fundraiser.

How does it feel to have a hand in planning this event considering this year is the 25th anniversary?

It means a lot. I volunteered for this event for almost ten years before I came on board and started planning it, so being here for the 25th anniversary just means the world to me. I love that I get to be a part of celebrating an event that has lasted 25 years. It’s an historic event that the community loves, not only here in Central Florida, but people are coming in from all over the country this year to be a part of this historic moment.

What special surprises are planned for the anniversary?

We’re not doing the headdress competition portion. It’s always been done, so this is the first year that we’re not going to have it in the show. The reason why we’re doing something different is because we want to celebrate the Headdress Ball — the headdresses and their history. So we have partners from all over the state of Florida who are building historic headdresses that represent the changes over the years. We’re doing four presentation components throughout the show that will showcase the history of the Headdress Ball through headdresses.

How excited are you to be welcoming Chad Michaels and Debbie Gibson?headdress_copy

Ridiculously excited. [laughs] The thing about this year is that it’s all about legends. Our
celebration this year is going to be legendary, and there are going to be key portions of the production this year that will be focusing on iconic legends. So we have Chad Michaels coming and he’ll be doing what he’s famous for, his amazing Cher impersonations. Debbie Gibson is going to be doing a number in the main show and then she will be performing a mini-concert at our after party. This is the first year we’ve done an after party.

We’re also welcoming local legends such as Leigh Shannon, who will be impersonating Bette Midler, and Tasha Long, who will be doing Diana Ross.

What do you look forward to the most when it comes time for the Headdress Ball?

I love the planning and the execution of the event, but what I look forward to the most is that night. This event takes six or seven months of planning, and sometimes the days feel like they run together and you don’t even know who you are. I love how all the people involved — our volunteers, our production people, our sponsors, our entertainers — work so hard to put an event together that celebrates the iconic image of Headdress Ball, and at the end of it all people are enjoying the show of the year, and they kick back and have a good time. I like that we can organize an event that is a fundraiser for HIV and AIDS and we end up celebrating life.

The Hope and Help Center of Central Florida has served people affected by HIV and AIDS since 1988. For more information, visit or follow their updates on facebook by “liking” their page at