You have to just believe
Claire Caplan – You have to believe.
Claire, an only child, was born and raised in St. Louis, Missouri. Her mother, Leslie Caplan, a professional singer and classically trained, performs with the St. Louis Symphony Chorus and has performed at Carnegie Hall several times. She always encouraged Claire to sing.
She sang in a local children’s choir but hated it and had no interest in singing, until recently. Claire attended a community college and was interested in professionally training dogs. She applied, and was accepted, at Duke University to study Evolutionary Anthropology, as it related to canine and human evolution.
In 2015, her godmother, who lives in Key West, asked Claire to house sit and take care of her dog over the summer. In late July, Claire was at the Hog’s Breath listening to the band, Patrick and the Swayzees. 
During a break, Jerrod Isaman was playing a Britany Spears song on the side of the stage and Claire started to sing along. He noticed, asked if she was a singer, and invited her to attend a rehearsal. They practiced a few songs together and then Claire was invited to sing a duet with their lead singer, Les Greene, at the Green Parrot.
At the end of the summer, Claire returned to St. Louis but came back to Key West in October and began performing fulltime with Patrick and the Swayzees, at the tender age of 25. Claire was ready but was never really comfortable going from “zero to 60”. Her first performance with the group was at the Sunset Pier. She told Les, “I can’t tell whether I’m going to pee or throw up.” He said, “You’ll get used to it.” … next up, a huge show at the Green Parrot.
Patrick and the Swayzees became a very successful Key West band and started touring. Les Greene still tours with them today. Claire did not stay for a number of reasons – touring, pressure, and a constant struggle to believe in herself. She left the band in February 2016.
Landon Bradbury put together a show at the Key West Theater on February 13, 2016 and hired Claire to sing three songs. Afterwards a woman approached and offered to book Claire at The Porch, the Other Side, and several other venues. She learned a ton of new music and quickly moved on to performing jazz standards.
In spite of her initial success in 2016 and most of 2017, Claire felt she was living someone else’s dream and struggled to believe in herself. It just didn’t make sense to Claire why so many wanted to hear her sing. It was a constant internal battle. She moved back to St. Louis in the summer of 2017 and had no intention of singing again.
Later that year, she received a phone call from Larry Baeder asking her to audition for Ben Harrison’s musical, “Undying Love”. She returned in January 2018 to perform in the very successful musical. She continued musical performances and struggled with managing her demons, and again, returned to St. Louis. She was planning a return to Key West in early 2020 when COVID shutdown the world.
After struggling mentally and physically, she took her last drink in March 2021. The withdrawal took a toll, and she couldn’t bring herself to get on stage and perform. Finally, one night she was in Scotty’s sitting with Fred Covan and his late wife Diane, who was battling cancer at the time. Diane asked if she would sing. Claire apologetically declined several times but Diane would not hear of it. Diane knew of Claire’s struggles physically and mentally. 
Diane took off her wig, looked at Claire and insisted, “I’m dying and you’re going to sing for me.” From that moment, Claire began to heal. She got on stage and performed with Ross Brown. Music and singing has helped stabilize her life. Her health is much better. Claire credits Diane and Fred Covan with her recovery.
A little less than a year later, Claire was on stage with Joe Dallas performing with the Paradise Big Band – Thank you, Diane. After working through her recovery, Claire began performing at Little Palm Island and Blue Heaven. Keith Snyder, bass guitarist with Happy Dog band, encouraged Claire to perform jazz with him and Smilin’ Bob Boyd.
Recently, she had a musical experience that went beyond her wildest imagination. She was invited on stage at the Little Room Jazz Club with Christine Cordone and Larry Smith. Larry asked her to sing Lucinda Williams’ song, “Fruits of My Labor”. Larry and Christine sang backup harmonies. It’s a great story, an inspiring song, and combined with the love of her friends, it brought tears to her eyes. It was a very special moment.
February 13, 2017, Claire leaves Patrick and the Swayzees and began singing Jazz at the Key West Theater. Six years later – to the day – February 13, 2023, Claire Caplan receives an award for Best Vocalist in Key West. At the awards ceremony, Claire performed her original song, “I Only Want to Kiss You”. Afterwards, another award winner asked Claire about the song. She thought it was an old forgotten jazz standard that Claire discovered and made new again. Claire considered that quite a compliment. She is finally starting to believe in herself. That’s good, the rest of us have believed in her all along.
Thank you.🥲
I first met Claire only a few days after she was born…. This story makes me happy and very proud of her…..
Having met Claire through activism in St. Louis, reading your
Article is especially inspirational
in highlighting Claire’s personal journey through the inner voices
that can keep us from our own authenticity and creative potential.
That she is now sharing her creative gifts to bring others
is indeed a triumph of courage over fear, of self love over self hate,
over willingness to create new healthy messages within, over ruminating in old messages which
hold us back from our
inner creative growth potential, sabotaging our inner joy, our authentic essence.
We embark on change, when we face our inner demons, confronting
them with self honesty …loving and forgiving ourselves, not letting what others say define who we are
as human beings.
Realizing that, though we are creatures of habit, we can also be creatures of healthy change, courageous enough to reprogram our inner computer, and live the holistic journey, however challenging,
to become kinder, more self-compassionate, loving and forgiving ourselves…
Open to releasing the creative joy
helping lift up others during these challenging times, which we collectively share.
Claire’s journey can be experienced through our own tenacity, resilience, and our courage to face our own personal fears. To embrace each moment, as well as ourselves, with unconditional love. Bravo Claire!
Encore!!
I am now, and always have been unspeakably proud of my extraordinary daughter! She is a consummate artist. She doesn’t just sell a song, she inhabits it. And on top of that, she is a total mensch, a completely loving and caring human being. I could not be prouder of her!