After moving to Arizona in the early 2000's, Penn won "Funniest Person in the Valley" contest three times, an honor that has allowed him to open for nationally recognized comics like Larry the Cable Guy, Jim Breuer and Billy Ray Cyrus or now known as "Miley Cyrus’ Dad." Penn’s act consists mainly of funny stories called from life with his wife and family. Penn takes audiences on a funny ride from child birth to adolescence, entertaining audiences from California to New York.