Sideline, band photo sitting on the stairs of the entrance to a wooden house

Sideline, a Formidable Bluegrass Band

North Carolina bluegrass band Sideline got together in 2012. Initially, it was a jam band featuring friends who played professionally in other bands. Founders Steve Dilling and Skip Cherryholmes each command their own historical significance within bluegrass circles, having garnered acclaim as integral members of prominent ensembles. They have also performed at the influential Grand Ole Opry on numerous occasions and traversed the national and international circuits highlighting their talent.

Although it was originally conceived as a mere diversion for these seasoned musicians, Sideline swiftly ascended to prominence. The band transitioned from a peripheral side project to a focal point of their artistic careers, marked notably by a commitment to prolific album releases.

The crowning achievement of Sideline’s trajectory came to fruition in 2019 with the prestigious accolade of the IBMA Song of the Year Award bestowed upon their chart-topping single, “Thunder Dan.”

The ensemble plays exhilarating music with heartfelt lyrical delivery, immaculate timing, and nuanced dynamics. What began as a casual foray into musical exploration during downtimes has evolved into a cohesive ensemble of virtuoso instrumentalists and vocalists, now fully immersed in the pursuit of their collective musical vision.

This high energy repertoire is augmented by the band’s onstage charisma and finesse, underscored by their harmonies.

The song “Thunder Dan” stayed at the #1 spot on the charts for multiple weeks, as well as the #1 song for the entire year 2018. It also won the 2019 Song of the Year award with the International Bluegrass Music Association.

Moreover, Sideline has had many chart-active/chart-topping hits, including, “Just A Guy In A Bar”, “I’ll Always Be A Gypsy”, and “Jesse’s Barn” from the album Ups, Downs and No Name Towns.

The three founding members Steve Dilling, Skip Cherryholmes, and Jason Moore guided the band until Jason’s premature passing in November 2021. Steve and Skip decided to continue with the band in honor of Jason’s commitment to the band and love for music.

In February 2024, Sideline unveiled a new single, “The Lives of the Innocent, after a hiatus of two years, marking a resounding resurgence in their creative output, a touching narrative set against the backdrop of the Civil War.

Band Members in 2024 included Skip Cherryholmes – guitar; Steve Dilling – banjo; Kyle Windbeck – bass; Nick Goad – mandolin; Andy Buckner – guitar.

Discography:

Session 1 (Mountain Fever Records, 2013)
Session 2 (Mountain Fever Records, 2015)
Colors & Crossroads (Mountain Fever Records, 2026)
Front And Center (Mountain Home Music Company, 2018)
Breaks To The Edge (Mountain Home Music Company, 2019)
Ups, Downs And No Name Towns (Mountain Home Music Company, 2021)

Author: Angel Romero

Angel Romero y Ruiz has dedicated his life to musical exploration. His efforts included the creation of two online portals, worldmusiccentral.org and musicasdelmundo.com. In addition, Angel is the co-founder of the Transglobal World Music Chart, a panel of world music DJs and writers that celebrates global sounds. Furthermore, he delved into the record business, producing world music studio albums and compilations. His works have appeared on Alula Records, Ellipsis Arts, Indígena Records and Music of the World.
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2 Replies to “Sideline, a Formidable Bluegrass Band”

  1. Malpass Bro’s are needing bluegrass for their new show. Heard them talking about it on Realrootsradio.com. Please contact Chris & Taylor. I’d love to see y’all on their show The Malpass Bro’s Show on RFD-TV starts 5/25. I know ur retired but i know you retired but I remember you said you may still do some special shows. Please let Chris & Taylor let them know if you have interest. Y’all are amazing.

  2. You guys are fantastic. The real deal! Love your band and hope you keep it up.

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