Fairest of the Fair 1999 – Charlynda Scales


A term often used carelessly or incorrectly.

But when referring to 1999 Fairest of the Fair Charlynda Scales, the term aptly applies.

As the first black woman to win the competition, she pushed the pageant and the surrounding community onward. 

Reflecting back on her victory, and the monumental cultural swing her crowning represented, Charlynda stated, “When they called my name, I remember seeing my friends jumping up and down with their posters. My mother was crying out thanks to God as she ran back and forth in front of the stage.” She added, “The previous Queen, Brandi, came up to me to place the sash and crown on. Her hands were shaking and she fought back tears. It wasn’t until that moment I realized the monumental shift forward that just happened in the history of our town.”

Charlynda acknowledged recognizing the weight of what the moment could mean for future competitions in the early moments following her victory.

She explained, “Directly after the crowning, I walked with my mom and friends through the fairgrounds. Seeing jaws literally drop to the floor when they read my sash reinforced the importance of the moment.” Charlynda continued, “After the pageant was over, it was late in the evening, but I drove straight to my grandparent’s house to show them. Their reaction, the starry-eyed stare with happy tears, will warm my heart forever.”

Following her victory, Charlynda’s social circle (then, mostly athletes who were track or soccer teammates, or fellow Girl Scouts) and public perception changed almost immediately. She had become a representative of the talent, grace, and goodness of the area and didn’t take this new responsibility and honor for granted. 

“Walking back into CHS after winning was surreal. It was as if I was once invisible, and now people could see me. I felt a big responsibility to bring honor to the title, knowing that I was representing all of the circles and cultures I represented,” she happily recalled. “Additionally, I now had a feeling of confidence I didn’t have before. I loved doing community service projects, reading to kids, and giving back to the people of Putnam County. It really was a catalyst to the work I now do on a national level.”

It’s been more than two decades since Charlynda changed Fairest of the Fair forever.

During that time she has served her country through military enlistment (even finishing runner-up for Ms. Veteran America) and ignited fires in minds across the country via her current role as a military influencer, speaker, and brand coach. In all things, she’s been a worthy ambassador for the Upper Cumberland’s most beloved pageant by living her life with dedication and selflessness.

Charlynda Scales redefined Fairest of the Fair and remains an icon for all young women of color who hear her story.

We’d call that revolutionary. 

– by Andrew Buckner, photo by Cris Stroud




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