Crying Uncle: From kids on bluegrass to young band on the rise

Crying Uncle performs a not-to-miss concert on Saturday at HopMonk Tavern in Novato.

It’s been two years since I first saw a young bluegrass band called Crying Uncle fill Old St. Hilary’s Landmark in Tiburon with some of the most spirited and skilled acoustic string music I’d heard in as long as I can remember. What was most remarkable about it, all four band members were teenagers.

I’ve been wanting to write about them ever since, but the timing never seemed to work out. Until now. I waited until you can hear and see for yourself what I’m talking about when this extraordinary quartet of young pickers plays at 8 p.m. Saturday at HopMonk Tavern in Novato.

With two more years of experience and maturity behind them, they’re even better now than they were when I first heard them on that jaw-dropping afternoon in Tiburon. And they’re coming off the highlight of their young career. In September, they won the International Bluegrass Music Association’s Momentum Band of the Year Award in Raleigh, North Carolina.

To show you how prestigious that award is, previous winners include the young guitar ace Billy Strings, who’s won the IBMA Entertainer of the Year Award three years running and whose album, “Home,” won the 2021 Grammy for best bluegrass album. Bluegrass fans may also recognize another former winner in singer-guitarist Molly Tuttle, a nominee for best new artist in all genres at the 65th Grammy Awards earlier this year.

“The Momentum Award means up and coming, a band that you should keep your eyes on,” says Miles Quale, Crying Uncle’s 19-year-old fiddle player. “The other bands in the running were amazing, so we’re so happy that we got it. We were very excited. Our parents were screaming.”

The night after the awards show, Crying Uncle performed at mandolin icon David Grisman’s induction into the Bluegrass Hall of Fame in Raleigh, sharing the stage with mandolin stars Ronnie McCoury and Sam Bush, “the father of new grass,” who was also inducted that evening.

A former Mill Valley resident now living in Sonoma County, the 78-year-old Grisman, who famously performed as a duo with the Grateful Dead’s Jerry Garcia, is the inventor of “Dawg music,” a blend of bluegrass, gypsy jazz, world music and other acoustic styles. He’s been a mentor to Crying Uncle as well as a major influence on their music.

“Playing that night was just as big an honor as winning the award the night before,” Quale says. “David is just a monster in this genre, and Crying Uncle is a band that’s known for playing Dawg music. And to get Ronnie McCoury and Sam Bush to come up on stage with us was pretty amazing.”

Quale and his younger brother, 17-year-old whiz kid mandolinist Teo Quale, formed the core of the band in 2016, naming it after a brotherly wrestling competition to see which brother could make the other “cry uncle,” or give up, first.

“But some people think it’s a metaphor for the competition between Teo and I on stage,” says Miles Quale, laughing.

The Quale brothers, original Crying Uncle guitarist John Gooding and bassist Andrew Osborn, now 20, who grew up in San Rafael and graduated from the Marin School of the Arts, met in the Kids on Bluegrass program at the California Bluegrass Association’s Father’s Day Festival in Grass Valley. They all sing as well as play their instruments.

Their career began to take off in 2018, when they won the best band contest at Pickin’ in the Pines, a major roots music festival in Flagstaff, Arizona, going up against adult bands from across the country. Since then, they’ve performed at San Francisco’s Hardly Strictly Bluegrass, the High Sierra Music Festival, DelFest in Maryland and the La Roche Bluegrass Festival in the French Alps, the largest in Europe. They’ve toured in Japan and Finland and have released four albums.

They recently hit a bump in the road when their original guitarist moved to Nashville to perform and tour with the Little Roy and Lizzy Show, a bluegrass group from Georgia. As luck would have it, Crying Uncle found his replacement this past June at the CBA’s Father’s Day Festival, the same festival where the boys in the band originally met. The Eureka moment came when bassist Andrew Osborn’s father, Joe, a two-time winner of the California State Senior Fiddle Championship who has also won the Western Open Senior Fiddle Championship, happened to jam with a hot young guitarist named Ian Ly.

“I thought, oh, my god, where did this guy come from?” Osborn remembers. “I could see he was about the age of the Crying Uncle kids and I had never heard anyone who could keep up with them. He was the perfect replacement.”

Like his new bandmates, he was inspired by the music of David Grisman and Jerry Garcia. After he was asked to join the band, the 22-year-old guitarist promptly went out and won the National Guitar Flat-Picking Championship in his native Kansas.

What’s impressive to me about these young musicians is that they are all students who also have lives and interests outside of Crying Uncle.

After graduating from the Oakland School for the Arts, Miles Quale was awarded a $25,000 Whippoorwill Arts Fellowship, spending a gap year touring the world, playing and recording with an international cast of musicians. He plans on releasing an album of music from his travels. He’s now a freshman at the University of California, Los Angeles, majoring in global jazz and astrophysics. Teo Quale, a senior at the Oakland School for the Arts, hopes to follow in his brother’s footsteps, taking a gap year before entering college.

Andrew Osborn, who plays trombone as well as bass and has performed with the Marin Symphony Youth Orchestra, is in his third year at Cal Poly San Luis Obispo, majoring in mechanical engineering. Ly is a graphic design student at San Francisco State University.

The band gets together for important gigs, like this Saturday’s at HopMonk, during breaks from school and for the summer festival season. They’re booking a full schedule of festivals and shows for next year.

“We’re all in the same age group and the same place in our lives so we get along pretty well,” Ly says. “We’d like to put together some tours and record an album sometime soon. I’d like to keep making music with them for as long as I can and see where it goes.”

• Details: Crying Uncle performs at 8 p.m. Saturday at HopMonk Tavern at 224 Vintage Way in Novato. The Cross-Eyed Possum Band opens. Admission is $20 in advance and $25 at the show. Get tickets and more information at hopmonk.com/novato.

Contact Paul Liberatore at p.liberatore@comcast.net