Sideline Success

By Greg Tutwiler
According to Webster’s dictionary, one meaning for the word sideline is “a job that is done in addition to your main job.” For the guys in the band Sideline, that’s exactly what it meant, at least in the beginning. But now, for Steve Dilling, Jason Moore, Skip Cherryholmes, and brothers Brian and Nathan Aldridge, it’s sideline no more. “Sideline sort of turned into full line somewhere along the line,” quipped co-founder and banjo player Steve Dilling, as we sat down recently at IBMA to talk about this relatively new, and certainly up and coming bluegrass band.
A veteran musician himself, Dilling got started in the mid-80s in a regional North Carolina band called the Bass Mountain Boys. From there he spent about six months with the Lonesome River Band before landing a more permanent gig with Russell Moore and IIIrd Time Out in the summer of 1993. Although he left that band in 2013, Sideline had already become a “side” venture for Steve and several other musicians, and a way to play when their main bands were off the road.”
Pieces Coming Together
“It started about five years ago,” Steve said. There have been different configurations of the band. Guys like Darrell Webb, Adam Steffey, John Chapman, and Ron Stewart all sat in with them at times but it kind of started settling in when Jason came on board.
Jason Moore got his start playing with the legendary James King from 1993 to 1999. He participated with two Michael Cleveland projects before joining the acclaimed Americana/bluegrass band, Mountain Heart, where he toured  until he joined Steve and Sideline in 2014. An accomplished session player, Jason has appeared on nearly 100 different studio projects and has produced two others.
The third partner in the trio, Skip Cherryholmes, played guitar for the famous traveling family band, Cherryholmes for almost 13 years until they decided to disband in 2011. In that time, they won the 2005 IBMA Entertainer of the Year award, and were nominated for numerous awards including five Grammys. He was playing with Lou Reid and Carolina before finding his way into the Sideline family, literally.
“My daughter and Skip got engaged, and he move here to North Carolina,” Steve said. “So naturally I wanted to pick with him. We knew we had a foundation of something that felt really good. So we invited Brian Aldridge and his sixteen year old brother Nathan, sons of long time Carolina musician Mike Aldridge, to round out the band. Those guys are both very talented musicians from a long musical background.”
Hitting The Stage
The guys got booked for their first bluegrass festival while they were still in other bands, but it was encouraging, and they started thinking about booking some additional dates. Steve had recently left IIIrd Time Out due to some health issues. “I just needed to stay close to home and get my health straightened out,” Steve said. “We decided to record a CD so we could have something to sell at the few gigs we already had booked. That CD did pretty good, and things just really took off after that.”
Jason was ready to make a change and he wanted to work for himself after years of working for someone else. The success of that first CD was enough to “go for it,” as Steve put it. “We went full force from there.” Jason, Steve, and Skip formed a partnership, and Sideline officially became full line. “That was actually just a little over a year ago,” Jason added. “We went from 30 dates last year to 80 this year (2015),” Steve said. “We’re blessed, really,” Steve said. “Some full time bands don’t even work that much. But the three of us have done this for so long, and we have a lot of connections, and contacts, and friends. So we’ve used that to our benefit.”
Jason said that the whole thing wasn’t even super intentional until about six months ago. “I was kind of done,” Steve said. “I was happy with 30 dates a year like we did last year.” Steve had gone to work for Jordan Entertainment, Loraine Jordan’s business, and thought he had settled into a day job. “She’s very understanding and supportive,” Steve said. “She even said, ‘I knew you would never quit. It’s in your blood.” “We had to let that run its course,” Jason quipped. “Then the bug started getting at him again.”
Doing It Differently
Steve was finally getting healthy again and the band was really starting to click. The challenge now would be to keep it from getting out of control on the other end. “The goal is if we can do the same amount of work in two or three weekends a month instead of four, then we still get to have time at home,” Skip said.
“For so many years, all of us worked all the time. I joke on stage that Skip, with the family band practically living on the bus, worked 600 days a year,” Steve said.
“Our family would leave at the end of August and not come back until the first week of November,” Skip told me. “You could do that then because you’re with your family. You’re not leaving anybody behind. But I couldn’t do that now.”
“For 17 years, we played every weekend accept the month of December, Easter weekend, and one week in July,” Steve said, “when I played with IIIrd Time Out. For Sideline, we’ll work heavy for three or four weeks, and then take a couple weeks off. And if one of us wants to be off down the road, we just bring it to the band, and then we’ll schedule around it. It keeps sanity and relationships in tact that way.”
Liking who you play with is important too of course. “We’ll have these two weeks that we’ll work, and then we’ll take two weeks off. But there’s going to be some kind of reason, either the three of us, if not the five of us, that we’ll end up calling each other during the break,” Skip said. “We actually miss one another,” Jason added. “We enjoy playing together,” Steve said.
“We have a family atmosphere too,” Jason said. “If you want to bring your wife, that’s fine.” “We even vacation together with our families,” Steve said. “We get a big beach house at the Outer Banks for the St. Patty’s Day festival in Manteo. We play in the parade and then hang out at the beach for a week.”
“As long as we continue to do things like that, this will stay fresh and we’ll keep having fun,” Steve said. “You know, this business is hard on your wife and family. My daughter is married to Skip. She was raised with me being gone, and now she has a husband on the road. She’s a veteran, she knows how to deal with it, and still it’s hard.” “I’m very blessed because of her understanding,” Skip added.
The Long Run
“2016 looks ever stronger too,” Jason said. With the second CD currently in circulation, Session II, they are working on their third, initially titled Session III, set to be out sometime in early 2016. While the band doesn’t currently write their own material, they do have a lot of new songs collected from some very good songwriters. Of course there are few covers including an old Johnson Mountain Boys tune that will feature Dudley Connell as a guest performer.
So the future looks solid for Sideline. “I hope this is my last band,” Jason said. “This is my last run at it,” Steve said. “I’m in my 32nd year on the road, and I think this is a great band to finish out my career with, whenever that it is,” he quipped. “We’ve got something good here.”


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