
The Story Behind
Freeborn Entertainment
THE EVOLUTION OF FREEBORN ENTERTAINMENT
For founder Harley Wilt, music isn’t just a passion—it’s a way of life. Harley discovered his love for performing at an early age, writing parodies and entertaining locals in his hometown of Rapid Valley, South Dakota. From early gigs at karaoke nights and private events to growing his own business, Harley has poured his heart into every moment. In 2004, he launched Generations Music, which evolved into Freeborn Entertainment in 2010, a name inspired by a nickname given to him during the Sturgis Motorcycle Rally.
Today, Freeborn Entertainment is known for creating unforgettable events, from romantic weddings to high-energy karaoke nights. With years of experience, professional equipment, and a dedication to making every event magical, Harley and his team continue to bring joy and music to every stage they step on.

Melissa S.
"I’ve seen this entertainment in numerous different settings. They are AMAZING! I want to have a 10 year anniversary party in September 2024 & I intend to have Harley be our entertainment! I cannot wait to see what this company does with its expansion!"
Misty A.
I recently had Harley provide karaoke for a birthday celebration! It was a great turn out and everyone had a fabulous time. highly recommended!
Ronda Jo M.
We have had Harley entertain our customers at Bullwackers Bar twice with a third event planned. We've had so many positive comments from our customers!! Harley is professional, fun and a talented entertainer!!