Ross Whitaker was born in Lexington, Kentucky. After studying guitar at both Bellarmine University and Cincinnati Conservatory of Music, he finished his B.A. in Music at the University of Kentucky in 2005. He later continued with graduate studies in musicology at the University of Kentucky, where he received his M.A. in 2013. His master's thesis categorized and analyzed "Louie Louie" borrowings in the officially released recordings of Frank Zappa.

As a performer, Ross has garnered a broad range of experience. He has recorded with Wycliffe Gordon, shared the stage with Bob Mintzer and Lorrie Morgan, and opened for artists such as Karl Denson, Brian Auger, Billy Joe Shaver, and Snarky Puppy. Ross performs regularly in and around central Kentucky on both guitar and pedal steel guitar.