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Sideline was formed in 2012 as a “jam band” for a group of friends that played professionally in other bands. They started playing together as a fun alternative when their bands were not performing. In a short time they discovered their own identity and style, and realized their tour schedule was getting full. They decided to take a leap of faith and commit to the group full time. The band was named “Sideline” by founding member Darrell Webb, due to its origin as a “side band”. Sideline has had different configurations over the years, but the three founding members Steve Dilling, Skip Cherryholmes, and Jason Moore led the band through it all until Jason’s untimely passing in November of 2021. Steve and Skip decided to continue on with the band in honor of Jason’s commitment to the band and love for the music.
In just under a decade Sideline has achieved a list of musical accolades. The song “Thunder Dan” not only held 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. 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 group’s latest album release “Ups, Downs and No Name Towns”. Both in title and in musical performance, this album reflects the band’s obstacle-ridden journey, while also acknowledging the recent struggle of the music industry — and especially its professional touring musicians — to cope with a months-long, pandemic-driven shutdown. The song “Old Guitar Case” (lyrical inspiration for the album title) delivers a depiction of the details of a road musician’s life, revealing profound truths about journeys of hardship and triumphs, victories and defeats — all undertaken with the aim of reaching new heights as the music and the community it builds continue to grow.
“In the musical slump caused by the shutdowns of 2020, Sideline decided to pull together and start on a new project. We had time, we had each other, and we decided to put it all to work in a way we had never done before. The inspiration and variety that make up this project really relate directly to the ‘Ups and Downs’ we were dealing with in real time. Working together to find ways to survive and remain relevant, while receiving dozens of calls day after day for canceled work — this became a whole new full-time, emotionally exhausting job. I truly feel that all of these experiences played the biggest part in the development of the music for this project. It affected every bit of attention and care to capture each performance exactly how we felt it, all the way down to the cover concept. In so many ways this tattered old guitar case represents the beating our band and career took through the pandemic. The fact that it still stands symbolizes our resilience and ability to persevere. Ups, Downs, and No Name Towns is by far the most musically developed project we’ve recorded to date, but it is also the most connected and inspired effort we’ve ever experienced, personally or musically.” – Skip Cherryholmes
Steve Dilling and Skip Cherryholmes are joined by Jamie Harper, Nick Goad, Andy Buckner, and Kyle Windbeck. Each with a commitment to working as one unit to deliver high-energy, innovative, hard-driving, variety-packed entertainment night after night throughout Sideline’s lengthy tour schedule. Always seeking new breakthroughs in music, while holding to the core of their proven success – A love for each other, a love for their ever-growing loyal fanbase, and a true love and passion for the music they create.