As the Po’ Ramblin’ Boys emerged as one of the most in-demand and important bluegrass bands of the past 10 years, its founding mandolinist C.J. Lewandowski didn’t focus only on the group’s art and career. C.J., now 37, became an avid collector and caretaker of music history, a board member of the International Bluegrass Music Association, and a record producer. All of those pursuits informed his latest project, a special one for the genre, because Keep On Keepin’ On is the final studio album by bluegrass Hall of Fame singer and mandolin player Bobby Osborne.
“C.J. had long wanted to record with Bobby Osborne, hoping to one day record a song or two with the legend,” writes Ohio broadcaster and historian Daniel Mullins in the project’s notes. “When he first began discussing a potential solo project with Turnberry Records, that was the original goal — to maybe have Bobby Osborne as a special guest on a handful of songs. Quickly, that initial idea transformed into something much more.”
Here’s why this matters. Bobby, who lived from 1931 until the summer of 2023, and his brother Sonny, one of the music’s legendary banjo players, got serious about recording and performing in the mid 1950s. Their base was Dayton, OH, but their roots, as with much of their audience, came from back in Kentucky, Virginia, and West Virginia, amid a great migration of labor from Appalachia to the industrial Midwest, as documented on the award-winning project Industrial Strength Bluegrass.
The Osborne Brothers became bluegrass giants, famous for thrilling three-part harmony that lit up hits like “Ruby Are You Mad,” “Once More,” “Making Plans,” “Midnight Flyer,” and the iconic “Rocky Top.” They joined the Grand Ole Opry in 1964 and enjoyed a decades-long hit-making career. When Sonny retired for health reasons in 2005 (he’s pass away in 2021), Bobby organized the Rocky Top X-Press as his new vehicle for making vibrant bluegrass music, and a way to keep his family in the music, with his son Bobby Jr. on guitar and bass.
Meanwhile, Lewandowski chased his own bluegrass dream in his home state of Missouri, and it’s not a stretch, he says, to think that the music saved his life. He was an only child being raised by a single mom when she died at age 33 when he was 10 years old. “I hated everything,” he says in an exchange we had that’s not in the interview presented here. “Because people took my mom from me, you know? So bluegrass music was the thing that filled that. It didn't feel it completely, you know, nothing's ever going to take the place of your mother. But it helped me. It was my medicine.”
At just the right time, along came the movie O Brother, Where Art Thou? with its pre-bluegrass old-time soundtrack and its powerful performances by Ralph Stanley and Alison Krauss. C.J. started getting around the acoustic roots scene every time he could, and to make a long story short, after working with area musicians for a time, he lined up a house gig at the Ole Smoky Distillery, a major tourist attraction in Gatlinburg, TN. That’s what led, in 2014, to the formation of the Po’ Ramblin’ Boys, a band with travelling in their name who didn’t have to move. They played long sets for visitors and honed their timing and sound.
Offers to play on tour, both in the US and Europe started coming in, and by 2017 they had a debut album out. The next year, they were voted IBMA’s Emerging Artists of the Year. They got picked up by Smithsonian Folkways for a couple of albums, a major coup for a classic-sounding bluegrass band. And they’ve been nominated as IBMA Entertainers of the Year several times.
Lewandowski met Bobby Osborne as fellow travelers on the festival circuit before his PRB days, but it was when he started taking a strong interest in vintage mandolins that the two had something to bond over. About 15 years ago, C.J. signed up for mandolin lessons with Osborne through the Kentucky School of Bluegrass & Traditional Music in Hazard, KY. One day the elder asked his student why he was coming out for lessons? C.J. replied that chiefly it was “to spend time with you.”
“(Bobby) said, ‘Oh, you don't have to do that. Here's my number. Just come over to the house anytime.’” C.J. recounts in the interview offered here. “And that was a turning point. I'd go over there probably once a month and hang out with him, and we might not even play mandolin. We'd talk about anything he wanted to. And it was very special to get to know Bobby, you know, other than the big white hat and the stones and the Grand Ole Opry star that we knew him as.”
That trust led to the album, a 13-song collection that was tracked in early 2023 at Ben Surratt’s studio in Nashville. It has a cast of friends and guests who are indeed special - Wyatt Ellis, Billy Strings, Molly Tuttle, Vince Gill, and more - but it’s Bobby Osborne’s vocal performances that make this thing meaningful. He was 91 when he recorded it, and there’s no “he sounds good for his age” thing going on here. It’s great bluegrass singing, borne of experience, the kind of vocals young tradition-minded artists aspire to, says C.J.: “You've got the age on his voice, and I wanted to capture that. I didn't want to clean him up so that it sounded like Bobby in the early 2000s. No, he was 91 and he could still do this stuff most people can't do when they're my age.”
And then there’s the repertoire, a mix of songs that C.J. and Bobby brought to the sessions, including some surprises. We hear proven classics like “Where The Soul of Man Never Dies,” “Cora is Gone,” and “Rank Stranger.” Plus some interesting finds, as CJ tells us about the title track. And most extraordinary is “Rocky Top,” the Felice and Boudleaux Bryant song that gave the Osborne Brothers a top 40 country hit and Tennessee immortality. On this album, you’ll hear Bobby Osborne’s last recording of “Rocky Top” and his final recording session of all time.
And with that, I urge you to listen to the full story in the interview posted here, covering the making of one of the landmark roots music projects of 2025.
