At 85, Bluegrass Legend Bobby Osborne Looks Back on Appalachian Upbringing & His Legacy

Stacie Huckeba
Bobby Osborne

"Kentucky Morning," a cut from Original, the new Compass release from bluegrass stalwart Bobby Osborne, definitely takes the singer back in time. He didn't write the song -- Darrell Scott holds that distinction -- but it brought back memories of growing up in the heart of Appalachia in the 1930s and '40s.

"I came from a little place called Thousandsticks, Kentucky," Osborne recalls to Billboard. "Back when my dad was a young man, times were so hard. We lived four miles from Hyden, and you couldn't get a car where we lived. You had to ride a horse or walk. We had no electricity or inside bathrooms -- practically nothing. Everybody in that part of the world raised a garden, and what you had to eat in the wintertime was what you raised in the summertime. So, we learned how to put it away. Everybody had a horse or a mule to ride, and a milk cow. It was hard living. Dad and mom saw a lot of that type of living. So did everyone. He went to Dayton, Ohio, started working, and came back and got the family. We got electric lights. I had never seen a refrigerator before. Every two to three days, a guy would come along, and you could get a twenty-five pound chunk of ice, fifty pounds or one hundred pounds to keep the food from ruining. When I was listening to the words of the song, it brought back a lot of memories."

Osborne's career started in the days of 78 rpm records; today, his latest project can be downloaded digitally. Original is the first album for the Grand Ole Opry performer since 2009's Bluegrass & Beyond. He admits that he thought -- at age 85 -- his days of recording music were behind him, but a guest collaboration with Peter Rowan led him to team up with Alison Brown and Compass Records to create music once more.

"We were out in Telluride, Colorado, and [Rowan] approached me about singing a song with him on his CD. He was recording for Compass, and Alison was producing it. I started to think about how much I was enjoying it, and maybe she might do one on me. I asked her, and the result of all of that is the new CD." Though it had been a few years since he made an album, Osborne likened it to riding a bicycle. "I hadn't forgotten or anything like that, but it was good to be back recording. Alison really made me feel right at home."

Osborne approached Original in a decidedly new-school fashion. The singer, who along with his brother Sonny blazed new musical trails for the format as The Osborne Brothers, recorded the album via the assistance of a grant from the FreshGrass Foundation, and in keeping with modern times, allowed his longtime fans to help fund the making of the album.

"Everyone that made a pledge toward the CD got something. There were a lot of different levels of sponsorship that you could do -- CDs, hats, posters, and all of that," Osborne noted. "I really enjoyed the process, and letting the fans be a part of the process. It was very new for me. I still don't know a lot about what all goes into it, but I know more than I did when we started."

Alison Brown, who produced the album and helped Osborne line up the grant and the financing for the project, says she was simply glad to give one of bluegrass music's greatest tenors a chance to paint from a new canvas.

"He made the comment that he didn't think he would ever get to make another record. That just struck me as something that I really didn't want to see happen," she says. "He needed to make another record. We had to get a little creative about how we would put it together, because he's not out there burning up the road, and the economics of selling music are more challenging than ever. We hooked him up with a grant, and got a pledge campaign going. Compass Records contributed too, and we made it work that way."

Brown says that his voice is just as pristine and as crisp as ever. "On some things, I hear his age a little bit – but in a really beautiful way. But, when he hits those high notes, that's the Bobby Osborne that we all know and love. It's almost like there is a depth that couldn't have been there 40 years ago. Now, to me, he's even better, because it's got both sounds," she said. "I'm really glad for the record to be out there for everybody's sake. It's great for Bobby to have a new record out, and for us to hear how amazing he sounds at 85 years old….It's truly inspiring. It's truly an honor and privilege. I'm just amazed that Bobby trusted me with his music. I'm really grateful for that."

Many of the songs on the disc have impressive pedigrees. In what is a career first, Osborne tips the covers hat to the Bee Gees via the set's first single, "I've Got To Get A Message To You," which was the pop group's first U.S. top 10 hit on the Hot 100 in 1968. It may take the casual bluegrass fan by surprise to hear a bluegrass record made from a Brothers Gibb composition, but if you have followed his career, you shouldn't be. The Osborne Brothers have had a history of recording songs from outside the traditional realm of bluegrass, including classics from the Eagles ("Midnight Flyer") and John Denver.

"I have always loved their harmony," he said. "I couldn't play that kind of music, but the harmony was always so good, and the songs were too. I picked out a couple of their songs for Alison to listen to, but I really didn't think that we'd do one because it was so far away from what I was used to doing. But I never programmed myself to be strictly bluegrass. I could sing country songs, and so many others. Alison said she liked that one, and I got busy and learned it." The song also lent itself to the making of a music video – another Osborne first. "That was something totally new. I didn't know what was going to happen. I had seen a lot of videos that other people had made, but I never thought I would be making one. But I really enjoyed it."

The stylist admitted that Brown was the perfect producer to steer the project, as she has an innate ear for how things should sound. Take, for instance, his version of Eddy Arnold's 1965 standard "Make The World Go Away."

"I had no idea what she had in mind as far as the type of songs. For every session, she knew the people to get to play certain parts or to do the harmony. I was floored by her ability. I went to the studio that day to record, and here sits Buddy Spicher and Matt Combs. I thought 'There's going to be some fiddle work on this one for sure.' They brought in the cello, and viola, and when they got finished with it, it was beautiful." Osborne had planned to add his own harmonies to the track, but Brown had another idea – Vince Gill.

"She asked me about having someone do the harmony on it, and I told her I was thinking about doing that myself. She wrote me back, and said she felt it needed a little bit. Vince did a great job with it, as well as playing mandolin on it, too."

As it turns out, Osborne is quite the Vince Gill fan. "I met him when he came here, and I always loved his singing. I have plenty of his records at home. I also love him as a person. A lot of people who get big in the music business lose a little bit of what made them in the beginning. Vince has never forgot about his raising, and I love that about him."

It's a mutual admiration society. When asked about his involvement on the track, Gill said "Bobby has long been one of my great heroes in bluegrass, and probably one of the main reasons I wanted to sing high. I loved the way he sang with Sonny and the trios that they had. If you go back throughout my bluegrass years, and I have recordings of me singing 'Once More' or 'Making Plans.' It was a real treat to get to sing on the project. Alison asked me to play mandolin on the track, and I said 'Are you nuts?' What a thrill to get to sing with one of my heroes. When you get the opportunity to share a microphone on record with someone you admire as I do him, it's pretty impactful."

Gill is just one of the special guests on Original. Brown assembled a supporting cast of musicians that run the bluegrass/Americana gamut – from Sam Bush to Jim Lauderdale to newcomers like Sierra Hull. She says that lining up participation for the album was pretty simple. "Everybody loves Bobby Osborne, and he's been an influence on so many generations," she affirms. "I really wanted to give the bluegrass community a chance to show that love, from the younger generation like Sierra Hull and Molly Tuttle to someone like Buddy Spicher, who has played on so many of Bobby's records in the past."

Though he might be in the twilight of his life, there is no slowing down for Osborne. In addition to his concert schedule and appearances on the Opry, he also shares his mandolin talents with students at The Kentucky School of Bluegrass & Traditional Music, a college in his hometown of Hyden, which allows him to keep in touch with his roots. "My dad taught school in that same building that I do. We teach the mandolin, the guitar, and the fiddle, dobro guitar, upright bass, songwriting, and everything to do with bluegrass music," he offered, saying that he wasn't sure if teaching was something he could do. But, he's glad he stepped up to the plate.

"My cousin became the director of the school. They opened it up in 2007. He told me they were going to have mandolin classes, and wanted me to teach them. I said I had enough of a time trying to teach myself, let alone somebody else. He told me to think about it, and that school was going to start in the fall. I thought about it, and decided I had done everything else that I knew to do. I might as well try it. It's worked out really good. You've got to have a lot of patience to do it. But, I have a lot of fun doing it. I've had some students that have gone on to be good players. Most of the students I teach range from 18 to 25. It's a two-year course at the college level. In the ten years, I've only had one student where nothing registered. I love doing that. I'll keep doing it until they tell me I can't do it anymore."

Whether it be as a mandolin instructor, musician, or perhaps the finest bluegrass singer in the format, Osborne will forever be known as one of the greats. How would he like to be remembered? "Nothing special. I just want to be remembered as a plain, ordinary simple guy that came from the country, and hit the big time, but I remained the same that I was when I first got started. I consider myself very lucky that I got to do what I've done. I've played music in all fifty states and some foreign countries, played for one of our presidents – got to sing 'Ruby' and 'Rocky Top' in the East Room of the White House. I'm very thankful. I've had a good life. I just want to be remembered as a plain and ordinary guy."