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.
Steve Dilling plays like he was born and raised in a crib where only Earl Scruggs and Tony Rice played on the twirling mobile above him. In love with the banjo at 10, playing by 12, starting The Bass Mountain Boys, then on to the Lonesome River Band, Steve's career has had a solid, steady trajectory of success and respect. He played 20+ years with Russell Moore and IIIrd Tyme Out. You know that Steve Dilling's Carolina-awesome banjo playing and hilarious emcee work is one of the main reasons you always go see them when they're in town. IIIrd Tyme Out has certainly brought his talent to the forefront of the bluegrass community. But his work with Sideline allows Steve to show audiences that he's the real deal in any setting.
Skip Cherryholmes started playing mandolin at age 9, but later switched to guitar when his family formed the "Cherryholmes" family band. Skip played with his family for almost 13 years until they decided to disband in 2011. In their time together, the Cherryholmes family won the 2005 IBMA Entertainer of the Year award, and have been nominated for numerous awards including 5 Grammy awards. He also played with bluegrass legend Lou Reid and his group "Lou Reid and Carolina". Although he now lives in NC, Skip is from Los Angeles, CA and loves to visit his family and friends on the west coast. When he's not on the road, he enjoys cooking and spending time with his family. He's also an Annual Passholder at Walt Disney World and tries to visit as much as possible!
Mocksville NC native Jamie Harper, hales from a family of performers. By the age of six he started learning guitar but the fiddle soon came calling, being the first in his family to play fiddle since his great-great grandfather. At a young age Jamie became a regular at many of the areas Fiddlers Conventions and Festivals further growing his love for music. Along the way he found interest in learning other instruments like mandolin, guitar, bass and banjo and also found an interest in other types of music. Starting his first full time position in 2003, Jamie has been fortunate enough to tour, record with some of todays top Bluegrass, Americana and Country performers in the US, Canada and Europe. Some of which include: Michelle Nixon & Drive, Donna Hughes, Carrie Hassler & Hard Rain, Still-House, Skip Cherryholmes Quintet, Marty Raybon, Blue Moon Rising, The Blue Dogs, Red Marlow, Junior Sisk & Ramblers Choice, and Claybank. When not on the road Jamie maintains a full teaching schedule with the Triad music group, spending time with family and friends, and fishing.
Nick Goad is a native of Stuart, Virginia. Growing up in an area rich in bluegrass music, he developed a love for the music at a young age. He began playing guitar when he was 9 years old and mandolin at the age of 12. He earned numerous awards including Best All Around Performer and 1st place in the Mandolin Competition at the Galax Old Time Fiddler's Convention. For the past several years, he has been a member of Jeff Brown and Still Lonesome, and he also has enjoyed playing and recording with several other bands. He recently acquired his MBA from Bluefield College, but because of his love of bluegrass music, he decided to continue his musical journey. When not playing music, he enjoys spending time with family and friends.
Kyle Windbeck is a multi-instrumentalist from Reston, VA who plays guitar, banjo, bass and mandolin. From a very young age he joined his dad on stage with various bands. He started playing the guitar at age 8, mandolin at 11, banjo and bass at 12. Over the years Kyle got to play with multiple local bluegrass bands in the Virginia-Maryland-Pennsylvania area and won numerous 1st and 2nd place awards at fiddler conventions. He is a Shenandoah University Conservatory graduate with a degree in music and an emphasis in live sound. Before joining Sideline, Kyle was an original member of Caleb Bailey & Paine’s Run, playing mandolin and running sound. When not on the road, Kyle works in his home recording studio, and plays music with Darren Beachley, former member of Doyle Lawson & Quicksilver.
Originally from Marshall, NC, now living in Granite Falls, NC & Nashville, TN, Andy comes from a long bloodline of family singers, songwriters & musicians. He grew up singing at North Fork Baptist Church just a few miles from his home in Big Pine, NC at the early age of 3. By age 7, he was touring regionally to churches with his Dad (Ricky) a singer, & his Mom (Shirley) also a singer & songwriter. By age 17, Andy was a multi-instrumentalist. Andy attended East Tennessee State University & joined the ETSU Bluegrass Pride Band as a freshman. While attending, Andy had multiple songs featured on FX tv show series “Justified”. Andy is also an alumni of NBC’s “The Voice”. Since then, Andy has been Grammy nominated, featured in “American Songwriter”, & has recorded with & had songs cut by; Tracy Lawrence, Montgomery Gentry, Charlie Starr of (Blackberry Smoke), Shawn Camp, Ronnie Bowman, Jerry Douglas, The Steep Canyon Rangers, Lillie Mae, Elizabeth Cook, Colt Ford, Casey Kristofferson, Terry Lee Palmer & The Ransom Devils, Matt Daniels, Sideline, & many many more. The 29 year old’s grainy soulful voice embraces his North Carolina roots & shares authentic songs inspired by his upbringing.
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