Darrell Webb

He was born in West Virginia in June 1974 and grew up in Jolo, a small coal-country village in the southwest of the state. His father, who worked in the mines, held frequent jam sessions at home and took him to instrument contests, pushing him to keep improving; Darrell started on mandolin at eight and later picked up guitar and banjo.

At nineteen, in 1994, he joined the Lonesome River Band as mandolinist and tenor singer, taking the place of Dan Tyminski, who had left to join Alison Krauss. In the later 1990s he went to J.D. Crowe and the New South, the first of two stints with Crowe, and around 2000 he left Crowe along with Phil Leadbetter and Robert Hale to found Wildfire, with Curt Chapman and Barry Crabtree. The band started out as the house bluegrass band at Dollywood and toured nationally. He also helped form the Nashville group Mashville Brigade, and through these years he was a first-call substitute on several instruments for Blue Highway, Mountain Heart, the Grascals, Larry Sparks and Dailey & Vincent, played on two Dolly Parton albums, and did some shows with Dierks Bentley.

He then played guitar and sang with Rhonda Vincent and the Rage, and in December 2008 he joined Michael Cleveland and Flamekeeper as lead singer and guitarist, making his debut with them on the Grand Ole Opry on 26 December. He played his last show with Cleveland on 21 June 2009 and started his own band. The Darrell Webb Band recorded Bloodline for Rural Rhythm (2010) and Dream Big (2014) and Lover’s Leap (2017) for Mountain Fever. Dream Big, made for his twentieth year as a professional and produced by Jim VanCleve, brought back many of the musicians he had worked with, among them the members of Blue Highway, Ronnie Bowman and Rhonda Vincent, who sang “More Love” with him; on “Pretty Polly” he played the banjo himself. Webb settled in Sevierville, Tennessee, and the band worked first at Dollywood and then regularly at the Ole Smoky Moonshine distilleries in Pigeon Forge and Gatlinburg. He was also an original member of Sideline, a group of Raleigh-area veterans whose first album, Session 1, came out in 2013. In May 2018 he announced that that summer would be the Darrell Webb Band’s last.

That July, Billy Blue Records signed its first act, Appalachian Road Show, a band built around Webb on mandolin and Barry Abernathy on banjo, with Jim VanCleve on fiddle, Todd Phillips on bass and Zeb Snyder on guitar. Its stage show tells the history of the Appalachian region between the songs; Webb has sung about his father’s death from lung disease after a life in the West Virginia mines. The self-titled debut album came out in 2018 and produced three No. 1 songs on the bluegrass airplay charts, and “Dance Dance Dance” was nominated for the IBMA’s Song of the Year. After the second album, Tribulation, the band won the IBMA’s New Artist and Instrumental Group of the Year awards in 2021, and it went on to be nominated twice for Entertainer of the Year. Jubilation followed on 7 October 2022, and the band made its Grand Ole Opry debut on 25 November that year; its fourth album, Della Jane’s Heart, came out on 23 January 2026. In April 2026 Webb, still touring with Appalachian Road Show, started a talent agency, Norabelle Entertainment, named, like his recording studio in Sevierville, after his two daughters.