Jonathan Vanderpool has a long history of performing with Orchestra Kentucky as well as other professional orchestras around the United States. He has been featured in Orchestra Kentucky’s Motown Madness, One Hit Wonders, A Rockin’ Christmas, Best of Retro, Country Madness, That 70’s Show, Roundup, Burt Bacharach, and Pet Sounds Live: A Beach Boys Celebration. 

He has also performed the roles of "Sky Masterson" (Guys and Dolls), "Cornelius Hackl" (Hello Dolly), "John Truett" (Meet Me In St. Louis), "The Father" (Sunday Pages), and various other opera theatre roles. He has performed with the Ramsey Theatre Company in the roles of "The Baker" (Disney's Beauty and the Beast) as well as understudy for Gaston and Maurice, "Lord Pinkleton" (Rodgers and Hammerstein's Cinderella), Lee Collins (Floyd Collins The Musical), and the Ghost of Christmas Present (The Best Gift: A Christmas Carol Musical) as well as understudy for Scrooge. He considers every opportunity to sing a gift from God.