Stand By Your Band


Stand By Your Band

The Women Behind Sideline, Weathering the Storm and Planning the Future

By Stephen Pitalo

When you’ve got a band that is used to a hard-driving sound, it’s hard to stay in neutral. During the pandemic, the members of Sideline have been finding ways to connect and to perform outside their usual comfort zone: Two of the members’ wives have emerged as leaders, strengthening their tight circle that includes band and family to meet all challenges that came their way. 

With a band like Sideline, founders banjo player Steve Dilling, guitarist Skip Cherryholmes and bassist Jason Moore needed to reassess their options; wives Macie Dilling and Stephanie Cherryholmes took the reins on certain parts of the Sideline operation in what has become the largest worldwide pandemic of the past century. These men may have been in highly-awarded groups, with multiple Grand Ole Opry appearances and years of national and international touring, but it was the strength of their partners in life that kept things on the right track. We spoke with the ladies to see just how the team at Sideline is working, coping and surviving. 

Stephanie Cherryholmes: It’s been stressful for sure, but we have been trying to do what we can to stay active on social media and keep the momentum going for the band. Skip has a home studio that he works in occasionally and he has been trying to work in there as much as possible. He is always trying to come up with ideas for the band to keep the band looking current. We try to do live videos as much as possible because it’s the best way to interact with the fans.

Macie Dilling: The uncertainty has been hard. I hear Steve getting phone call after phone call of shows getting canceled. So, we have had to become creative in ways to make a living and keep the band going strong. Steve has kept busy teaching lessons. He usually must cut down his schedule in the summer but since he has been home this summer, he’s had a full teaching schedule.

Stephanie: Skip and I both help each other with everything so it’s no different in the band. I help him with social media, keeping the website updated, merchandise, and staying organized. We try to sit down every Sunday night after Aiden goes to bed and come up with content ideas and any kind of marketing ideas to help the band. That wasn’t something we always had time for before the pandemic, so it’s been a nice thing to be able to do. In March and April, the only news was about shows canceling, so we had to get creative with ideas. It’s been a lot of fun to help him with it though.

Macie: Steve was playing music when we started dating, so this is the only life we have known. We are coming up on 35 years of marriage, so we have done this for a long time. I try to help Steve as much as I can keeping up with correspondence and reminding him to return phone calls. Sometimes I play the role of his personal secretary. I enjoy getting to interact with the fans. Sideline fans are the best and I can’t believe the support they have given us during these uncertain times. 


Stephanie: Since our son, Aiden, was born in 2017, Skip has been super busy. This is the most time Skip and Aiden have been able to spend together and it’s been so wonderful. It’s been nice to spend so much time together as a family. We have established a new “routine” together which is something we have never been able to do living off of a musicians’ schedule.

Macie:  It’s definitely been different having Steve home, but I’ve enjoyed the time we have spent together. My favorite thing we have been able to do is our morning time together drinking coffee on the porch, which I usually never had time to before when I had to work. We usually cook breakfast and have a leisurely, relaxed morning. 

Stephanie: Family life has changed a lot. Usually, I am used to doing my own thing, so at first, it was a big adjustment having Skip there all the time. It’s been so nice though. We have a new routine that we have really enjoyed.

Macie: Well I have had to learn to share the remote control. Our dog has really enjoyed having him there. But seriously, it’s been so nice having him home. The slower-paced lifestyle has been great to be able to experience together.


Stephanie: One of the Sideline Girls started a meal train for the family and that has been so nice. I also started an Amazon Wish List for my grandparents with essentials they have been regularly using. My grandparents have been so overwhelmed with all of the love and support. They haven’t had time to get online very much, but I have been reading them all of the comments and messages they have received from the bluegrass community. They have shared so much with musicians and fans through the last 40 years, so I am so thankful they are receiving some love back during this time when they need it the most. We say it all the time, but the bluegrass community has the best people in it.

Macie: After Easter, Steve’s dad (Don) started getting sick. We found out on July 5 that he had terminal cancer. Kind of knocked the wind out of our sails, but again with Steve being home, we have been able to spend much more time with him than he would have if he were on tour. I have a small group of friends that I call my Sideline Girls, and they have all come together and supported us in so many ways. Prayers, gifts, food – you name it. They have been there 100% of the way. It was such a nice blessing. From there, the bluegrass community found out and they have rallied around us. It’s been overwhelming at how much support we have had. Don and Linda have cried daily about how much love they have received from the bluegrass community.