Jon Shain

In 1998, Shain and Simonsen began work on what would become Jon Shain's first solo album, Brand New Lifetime, which ranged from the alt-country of WAKE to a more stripped down re-discovery of Shain's acoustic blues background. Shain began to play shows solo and with his new group, The Jon Shain Trio – composed of FJ Ventre on bass, John Currie on dobro and guitar, and Bill Newton on harmonica. This group stayed together the longest of any of shain's musical associations. Shain has recorded several albums on his own Flyin' Records and continues to tour and record regularly with FJ Ventre.

In 1997, Shain married graphic designer Maria Bilinski. The couple have one daughter, Johanna, born in 2002. Shain has written a song for each of them, both of which can be found on Army Jacket Winter.

In 1996, Shain and Simonsen started a new group called WAKE, with Kirsten O'Rourke Simonsen on vocals and Stu Cole on bass. In 1997, Cole left to join Squirrel Nut Zippers and he was replaced by Darrell Dixon on bass and John Currie on guitar. WAKE leaned more towards an alt-country sound. WAKE broke up in early 1998.

Shain attended Duke University in Durham, North Carolina, where he majored in history. It was during this time that Shain was introduced to the folk music of the region. In addition to playing in a frat-rock cover band, The Blind Mice, Shain began to research and play Piedmont blues. Shain joined The Slewfoot Blues Band, led by Mickey "Slewfoot" McLaughlin and "Sleepy" Tom Forsythe. Through Slewfoot, Shain met North Carolina blues artists such as Big Boy Henry, John Dee Holeman, Lightnin' Wells, and jazz pianist Brother Yusef Salim. Shain has described his style of blues as being based on Piedmont blues and has said, "I'm interested in the kinds of songs that aren't necessarily in standard blues progressions." Shain also took opportunity of Duke's jazz program, studying one semester with saxophonist Paul Jeffrey, a veteran of Thelonious Monk's group. Shain graduated from Duke in the summer of 1989, and immediately began pursuing a career in music.

In 1989, Shain and bassist John Whitehead formed a blues-rock duo, Flyin' Mice. They began to play shows at local clubs and festivals in The Carolinas and Virginia. Catching the ear of soundman and recording engineer Charles Jones, Flyin' Mice was signed to Jones' fledgling independent label Dr. Lime Records. The Mice expanded to a trio with the addition of drummer Mark Simonsen. In 1992, John Whitehead left the band and was replaced by bassist Aaron Oliva and Ben Saffer on guitar and banjo. Flyin' Mice earned the tag "psychedelic bluegrass" due to its incorporation of vintage bluegrass influences into its jam-rock performance style. This incarnation of the band gigged steadily up and down the East Coast until the band's breakup in 1996.

Shain has released ten solo albums, and has also recorded with the bands WAKE and Flyin' Mice. Since 1988, he has performed live with Jorma Kaukonen, David Grisman, Jackson Browne, John Hiatt, and others. Shain played electric guitar as part of Big Boy Henry's backing band in the 1980s.

Jon Shain (born Jonathan Bruce Shain, November 18, 1967 in Haverhill, Massachusetts, United States) is an American folk musician, guitarist, singer-songwriter, producer, teacher, and recording artist based in Durham, North Carolina. Shain is the 2019 International Blues Challenge winner in the solo/duo category.