In the tradition of roving troubadours Jack has carried the seeds and pollens of story and song for decades from one place to another, from one generation to the next. They are timeless songs that outlast the musical trends of any given day. He wrote one of the first trucking songs—Cup of Coffee—recorded by Johnny Cash, championed the works of new singer-songwriters such as Bob Dylan, Kris Kristofferson and Tim Hardin; and became a founding member of Bob Dylan's Rolling Thunder Revue. He continued the life of the traveling troubadour influencing Jerry Jeff Walker, Guy Clark, Tom Russell, The Grateful Dead and countless others.

Ramblin’ Jack is a two-time GRAMMY winner, National Medal Of Arts recipient, and in 2016, received a Folk Alliance Lifetime Achievement Award. Featured in the recent Rolling Thunder Revue film by Martin Scorcese and also in the early 2019 PBS release of the Woody Guthrie All Star Tribute Concert Center, Ramblin’ Jack is an icon of American roots and folk music. A lover of storytelling and veteran troubadour style musician, on tour he is in his element and known for telling the tales gathered along his magnificent journey through the roots of Folk, Blues, Americana and Cowboy music and poetry. His permanently enshrined seat at Woodie Guthrie Center Theater in Tulsa, OK, sits among other greats, including Lead Belly, Cisco Houston and Pete Seeger.