Jack began playing traditional music, much of it Appalachian and Bluegrass fiddle tunes, on the guitar in 1972. He found success in numerous guitar contests, winning the Knoxville World’s Fair Guitar Championship, the Galax Fiddler’s Convention Guitar Contest and the Wayne Henderson Guitar Championship. Jack also fed his passion for traditional music in the 1970s as the guitarist for Olen & Frances Gardner & the Appalachian Ramblers bluegrass band.

His recording “Dark Run” featured a wide variety of folk and traditional music as well as original compositions, leading Bluegrass Unlimited to call him “a fine quick-picker with a weathered welcoming voice”. In addition to playing fiddle and guitar with Celtibillies, Jack has toured the USA and Canada with New York Times Best Selling author Sharyn McCrumb, performing a program of Appalachian ballads based on Sharyn's Ballad Series novels. Their collaboration resulted in “If Ever I Return, Pretty Peggy-O”, Jack’s recording of the ballads from Sharyn's novel by the same name.

Jack has also contributed to the rich heritage of traditional music through his instrumental and vocal compositions, many of which are included in his recordings. These compositions include ballads based on regional historical events such as the 1912 courthouse shootout in Carroll County, Virginia and the 1946 mine disaster in the Great Valley Mines in McCoy, Virginia. The National Park Service Blue Ridge Music Center featured Jack in their Blue Ridge Masters showcase concert series.