Jack Holway was a member of The Cavaliers' tenor line in 2010 and aged out in 2011. Before joining The Cavaliers, Jack was also in the tenor line of the Crossmen Drum and Bugle Corps.

In 2011, Jack was a member of the WGI World Champion Music City Mystique. Since ageing out of DCI, Jack has been an active instructor and clinician throughout the Southeast.

Jack currently lives in Nashville, Tenn., and is the Battery coordinator at Franklin High School located in Franklin, Tenn.