The Tailgate Entertainer | Performers | Performance Business | Creatives | Artists | Talent Buyers

Tailgate Entertainer is a podcast about the fair industry and the exciting people involved in it. The goal of the show is to help those involved in the industry succeed by sharing years of collected wisdom. You will not find a more eclectic mix of people in the world than those that work at fairs. Their exciting journeys, lessons, and humorous anecdotes are woven together here to provide encouragement, education, and support for the industry.
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The Tailgate Entertainer | Performers | Performance Business | Creatives | Artists | Talent Buyers




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Dec 20, 2016

Welcome to my show everyone! Merry Christmas to you! Now, if you’ve never heard our show before, we are all about the fair industry. We don’t spend a lot of time talking about corn dogs or Ferris Wheels, even though those are two important parts. We spend most of our time talking about the amazing people involved, and that’s why I stay in it.

I decided to make this episode a Christmas episode, but that doesn’t mean I’m leaving out all the people who celebrate in a different way.  We have a fantastic guest coming your way, and her name is Teddy Anne Cunningham.

She is originally from Wyoming and lives there now with her husband and two kids. She has been playing at fairs for over 25 years, mostly with her brother Cal. They are both amazing artists. She told me a funny story about them growing up, she said they were “reluctant graduates of the wooden spoon youth movement program, under the supervision of Mama Lark Lindford”. Which kind of reminds me a bit of my mama as well.

I love her story, plus, she is a strong woman of faith, has an angelic voice, loves her family, and loves her career. You might want to put your headphones on for this episode because you’re going to hear some cool songs. I even included one that her brother Cal sings. So sit back ladies and gentlemen, here is Teddy Anne Cunningham.



  • She played with her family over 27 years ago for the first time because the band didn’t show up
  • Talks about her husband being a fair manager
  • Events that have happened in the fair industry that she needed to walk in faith
  • Did you feel the stronger your faith was, the stronger the resistance was?
  • As an adult, what kind of things are challenging you now?
  • Created to have a family and be a performer
  • It’s okay that Teddy is not a super established musician because Teddy has also concentrated on all her other dreams (like her family)
  • Everything Teddy does is for her kids
  • Mothers just spend all their time taking care of their kids, which is Teddy’s biggest challenge in taking care of her own career
  • John Dunnigan was her biggest aspiration as a kid
  • Teddy and her brother mostly perform locally
  • The ultimate dream for performing somewhere: meeting Vince Gill or Ronny Crowell
  • For self-improvement, you pray


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