By Steve Flairty
NKyTribune columnist
Raised in the community of New Castle, population 700, the thought of being a future Miss Kentucky wasn’t on Janie Olmstead’s radar. But she always knew she was going to college.
Turns out she did both, and that’s not bad for a small-town girl who has always been happy, simply, to “just do my best.”
Janie attended and graduated from the University of Kentucky, a dream realized. In 1966, she won the Miss Kentucky Beauty Pageant and was off to compete for Miss America, in Atlantic City, New Jersey — a place far from the quaint, homey New Castle where all knew and loved her. And though she didn’t win the title of Miss America, she carries a personal resume matched by only a few.
Today, as the owner of the successful Images Model and Talent Agency, based in Lexington, she is proud of the careers she has helped spawn for others to do what she did decades ago, performing in front of audiences with grace and charm.
Here are a few examples of notable successes who worked under Janie’s tutelage:
• Jeremy Sumpter, then a 13-year-old, received the title role in the 2003 film adaptation of Peter Pan.
• Kiami Davael used her training to gain the role, at age 10, of “Lavender” in the hit movie, Matilda.
• Joseph David-Jones is slated to play the oldest of Michael Jackson’s brothers in the movie Michael, scheduled for 2026 release.
And though her focus with Images hasn’t been on pushing the idea of pageants, Janie noted that in 2009, “Christy Stucker, one of my models, became ‘Mrs. Kentucky.’”
Looking back some 59 years ago, a lot happened before Janie, wearing her then popular “beehive” hairdo, won the hearts of the Miss Kentucky Pageant judges. Much of her success Janie attributes to her mother and a man she affectionately called “Bobby,” her stepfather.
Bobby Maloney married Janie’s mother when she was widowed at age 22. The two were a good team and made wonderful role models for their two children.
“I thank God every night that my parents were so supportive of everything my sister and I did,” she said. “They were raising us to be independent women.”
As a child, Janie rode her bike around the downtown square in New Castle.
“The courthouse was right in the middle,” she said with a grin. “I walked to school.”
She was a cheerleader in high school and served as president of the Kentucky Future Homemakers and was in the first graduating class of the then recently built Henry County High School.
While a junior, the Henry County Homemakers, who sponsored the Miss Henry County Fair Pageant, contacted Janie’s mother about entering her daughter. It was partly because, Janie recalled, that “they didn’t have many in the pageant and (they said) Janie needs to be in it.”
Janie agreed to the request with her proverbial mind-set of “doing my best.”
She didn’t win but was the first runner-up, gaining, she said, “a little taste of it.” Not bad for a start, especially when being in beauty pageants hadn’t been something she imagined doing. She entered again the next year and won, then competed in the Miss Kentucky County Fair but did not win. Janie admitted that she “wasn’t real serious about it. I represented Henry County and did the best I could.”
It was on to college at UK where she majored in health, physical education, and recreation and received scholarship help. Having already had what she called a taste of being in a pageant, she soon gained renewed interest. In the summer of her freshman year, she entered and won titles for Miss Carroll County Fair, the Miss Little World’s Fair at Brodhead, and Miss Orchard Grass in the town of LaGrange.
“I was in all kinds of things, and I was winning,” she said, though sounding as if she was surprised. Janie tended to question her talent level, even though she figured her genes were good. “My biological father could sing, play the piano and any instrument, and I got none of that.”
But obviously, she was doing something right, and at UK, she competed and won recognition as Kentuckian Queen, or as she called it, the “queen of the yearbook,” and she also won the prestigious Mountain Laurel Festival, in Pineville.
With the help of people in New Castle sponsoring her, Janie would enter the 1966 Miss Kentucky Pageant. Typical of her, she considered her talent as being on a mediocre level. She did, however, feel good about how well she could interview and how she looked in an evening gown.
“I went into it thinking that this was the only year I’m doing it, (and) I’m going to have fun and do the best I can,” said Janie.
She chose dancing for her competition talent and shared a humorous anecdote about it. “Our house in New Castle wasn’t big enough to practice. With my dad being the mayor, they backed the fire truck out of the firehouse, which was also City Hall,” she said, giggling. There she faithfully practiced her dance routine, where “right across the street was the jail. The prisoners were yelling at me and I’m waving and everything. I thought it was so funny.”
Janie figured, for a couple of reasons, that she had little chance to win the honor of Miss Kentucky. Her self-doubt about her talent was one reason, along with her own sense that competition officials already had someone else they wanted to win. “Well, I made the top ten, (then) the top five, and ended up winning, so much to my surprise.” She also took special pride in being recognized as Miss Congeniality, an award voted on by her peers.
The Miss Kentucky pageant was held in July 1966, at the Brown Theatre in Louisville, and with Janie’s win, her next stop would be to compete in September for the 1967 Miss America crown in Atlantic City. That year saw good fortune smile on Miss Oklahoma, Jane Anne Jayroe, for the award. But besides having the experience of a lifetime, Janie won scholarship money that she used to get her master’s degree in guidance and counseling.
Janie’s public appearances did not end when the Miss America Pageant was behind her. The next year became one of weekend commitments to all parts of the state. Janie, the reigning Miss Kentucky, was showcased around the state at parades and other public events. Where today’s Miss Kentucky winners take off a year for the grueling schedule, Janie continued to work as a full-time physical education teacher at Shelbyville Middle School. A chaperone drove her to appearance locations, but living in an isolated town made it more difficult to navigate, especially after returning at night from the events.
“She’d drop me off at Shelbyville and it would be dark and late, and I’d have to drive back to New Castle by myself,” Janie recalled.
Janie later married and spent time moving around the country with her husband in his military service, plus living for a while in Korea. In 1977, he encouraged Janie to start her modeling/talent agency with a $500 loan after they came back to Kentucky and settled in Frankfort.
Today, her Images business is a true achievement built on hard work, treating people right, and using life experiences that began in New Castle leading to becoming Miss Kentucky.
And all Janie Olmstead has ever asked of herself is to simply “do my best.” It’s worked out pretty well for her.