bluegrass
Raleigh, North Carolina
Photo: Laci Mack
Raleigh-based sextet Sideline has emerged as the consummate bluegrass touring band. It’s a labor of love, repaid by the adulation of traditionalists and newcomers alike across the Carolinas and far beyond. Their latest album, 2021’s chart-topping Ups, Downs, and No Name Towns, is a testament to their dedication; as guitarist Skip Cherryholmes says, “In so many ways this tattered old guitar case [on the album cover] represents the beating our band and career took through the pandemic. The fact that it still stands symbolizes our resilience and ability to persevere.”
Sideline was formed in 2011 quite literally as a sideline for a group of friends who were each touring with other influential bluegrass bands. This side project quickly became a hit with audiences, heralded for their songwriting and their beautifully blended harmonies, and a full-time focus for founders Steve Dilling, Skip Cherryholmes, and Jason Moore. The trio led the band together, garnering awards like 2019’s IBMA Song of the Year for “Thunder Dan,” until Jason’s untimely death in November 2021. That loss hit them hard, but Dilling notes they decided to embrace a mission of “trying to keep playing in honor of Jason, who gave us everything he had.”
Steve Dilling is the banjo player, elder statesman, and emcee of the band. As a kid he was infatuated with the banjo and wanted nothing more than to be on stage entertaining. When his dad bought him an instrument at age 12, it was a quick trajectory to professional life. His best-known previous gig was more than two decades with bluegrass sensations Russell Moore & IIIrd Tyme Out, which he helped found in 1991. That, of course, was not long after his Sideline co-founder (and now son-in-law) Skip Cherryholmes was born. Skip was 9 when his parents put together their eponymous family band Cherryholmes in 1999, and only 15 when they were named IBMA Entertainers of the Year. Now Sideline’s lead guitarist, known for his deep baritone voice as well as his hot picking, Skip also leads his own quintet … as a sideline.
The rest of the band is a veritable who’s who of other young bluegrass standouts. Fiddler Jamie Harper is multi-instrumentalist with an impressive touring and teaching schedule. Although he hails from a musical family, Jamie’s the first one since his great-great-grandfather to play the fiddle. Virginia native Nick Goad is a former Best All-Around and first place mandolin winner at the Galax Old Fiddler’s Convention, whose MBA doesn’t stop him from making a living as a bluegrass musician. Upright bass player Kyle Windbeck began to play professionally with his father from a young age, and is a many-time fiddle convention winner; he’s also graduate of the Conservatory at Shenandoah University. Sideline’s newest member is guitarist Andy Buckner. A touring Baptist church singer since age seven, Andy recently appeared on The Voice and was featured in American Songwriter. He has penned tunes for some of bluegrass’s biggest names. Turns out Sideline may have started as an aside but is well on its way to becoming one of those bluegrass legends.