.Molly Tuttle’s Album Debut

As she comes home to play the Guild Theater, Molly Tuttle longs for the California of her youth on her new album ‘Crooked Tree’

It’s the end of an era for Americana music in Northern California this year, with the last-ever Kate Wolf Festival coming in June. The prestigious folk and bluegrass gathering is going out on its 25th anniversary, with founder Cloud Moss citing fallout from the pandemic and uncertainty about the future of music festivals.

“Sleepy” John Sandidge, a DJ at Cupertino’s noncommercial radio station KKUP—who has also run the Kate Wolf Festival’s DIY radio station for many years—says both the event and its founder will be sorely missed.

“He’s just done everything for the right reasons,” says Sandidge. “He didn’t have the music-industry greed—he was more interested in the artists and the music.”

The festival’s end is also sad news for Palo Alto native Molly Tuttle, who says she always wanted to perform at it. But Tuttle represents the start of a new era for Americana, one that’s been coming for a few years now.

Her new album, Crooked Tree, is her major-label debut, but she didn’t so much storm the music industry as sneak up on it. Performing since the age of 11, the 29-year-old singer-songwriter has been winning competitions and scholarships—including to Boston’s Berklee College of Music—for a decade. In 2012, she was named Best Female Vocalist and Best Guitar Player by the Northern California Bluegrass Society, and appeared on A Prairie Home Companion. In 2015, she moved to Nashville after recording and touring with a couple of bands and collaborating with other up-and-coming artists in the genre. Regional and national awards became global recognition when she won the International Bluegrass Music Association’s award for Guitar Player of the Year—the first woman to do so. She won it again in 2018, as well as the Americana Music Association’s Instrumentalist of the Year.

By this time, Tuttle had released her first solo EP on the indie Compass label co-founded by banjo player Alison Brown, who helped to bust the glass ceiling for women instrumentalists in the genre. Tuttle followed with her debut album, When You’re Ready, two years later.

But despite a childhood steeped in the music—thanks to her dad, Jack Tuttle, who got his start as a renowned music instructor at Gryphon Stringed Instruments in Palo Alto in 1979, and has written a dozen books about bluegrass instrumentation—Tuttle’s first releases merely circled the bluegrass tradition, as she weaved through different genres, finding her own sound and voice. With Crooked Tree, however, she dives headfirst into her own musical heritage, taking a genre known for its formal structures and old-timey vibe and making it modern, immediate and personal.

Return to Grass Valley

Even with the Kate Wolf Festival on its way out, there are still an unusually large number of Americana festivals around NorCal, especially bluegrass festivals. A lot of them, says Sandidge, are just “a stage, a lot of people who love bluegrass, and a lot of picking parties.”

Molly Tuttle may not have gotten to play the Kate Wolf Festival, but she did play a lot of those bluegrass festivals growing up, and her new album features a moving tribute to those gatherings, “Grass Valley”—named after the city that is home to many of them, including the California Bluegrass Association’s annual, four-day Father’s Day Festival. Deadheads and tie-dye array/ Dog music devotees/Like nothing I had ever heard or seen,” she sings.It was jamgrass for the hippies/Old stuff from the ’50s/Just about nothing in between/I stood and tried to play along/Boy, I only knew a couple songs/While bolder kids sat in with the bands/I watched and envied from afar/Head bowed down over my guitar/Praying to catch that magic in my hands.”

“I think those festivals were where I fell in love with music,” says Tuttle by phone from the road on her current tour, which comes to the Guild in Menlo Park this week. “A part of me almost didn’t want to put that song on the album, because it felt so personal and so autobiographical. I wasn’t sure if it really fit with the other songs, but I feel like it shows a side of bluegrass music that people really love, which is, like, gathering with your friends at a festival and jamming under the trees—it’s all ages, there’s kids and older people. So yeah, I felt like that song kind of explained the whole making of the album.”

Indeed, Crooked Tree is a jam fest with friends old and new for Tuttle. Backing her on the album and on tour is her Golden Highway band: fiddler Bronwyn Keith-Hynes, bassist Shelby Means, Dominick Leslie on mandolin and Kyle Tuttle (no relation) on banjo. But six of the album’s 13 songs also feature guest appearances, like Old Crow Medicine Show on the swinging “Big Backyard.”

“I wrote that with Ketch Secor from Old Crow, and I wanted that one to sound like a backyard party and a jam that everyone’s invited to,” says Tuttle. “And they definitely brought the party. I knew that they would do a great gang vocal on that one, and just make it sound really fun.”

The cowgirl anthem “Side Saddle,” meanwhile, features Americana star (and UC Santa Cruz grad) Gillian Welch. “She’s just, she’s such a hero of mine. It’s such a dream come true to have her sing on the album. I sent her a bunch of songs, and I was like, ‘Please be on any of these. I would love to have you on the album.’ And she chose ‘Side Saddle,’ which I thought was perfect. Kind of a tribute to strong women,” says Tuttle.

Speaking of strong women, for the double-time outlaw love song “Over the Line” Tuttle drew from her Americana supergroup First Ladies of Bluegrass, although her ties to guest Sierra Hull go back even further than that—back to the Grass Valley years, in fact.

“We’ve played together since we were kids,” she says. “I met her when I was like 11 years old, when I went out to IBMA [International Bluegrass Music Awards], which I think was in Louisville at the time. My dad took me out there. And we were in this kids’ program together. So we’ve played together so much through the years, and she helped me work out the arrangement for that song; we played it together as a duo, and with our band the First Ladies of Bluegrass.”

For “San Francisco Blues,” Tuttle brought in 14-time Grammy winner and longtime Alison Krauss collaborator Dan Tyminski. But originally she’d hoped to collaborate on it with one of her biggest musical heroes—and one of the most famous bluegrass musicians to come out of the Northern California scene.

“I sent that one to Laurie Lewis, because I wanted to have a Bay Area singer on it,” she says. “And she was really excited to do it, and we had it all queued up. And then she got sick, and she lost her voice, and it was taking a really long time to recover. She wasn’t sure when she would get it back; she had to go to voice therapy. And so right at the last minute, she was like, ‘I’m really sad, but I just can’t do the song.’ And Dan Tyminski lives down the road in Nashville. And I was like, ‘I think you could come in at the last minute and save the song.’ And he did such an awesome job. And we were almost not even going to put it on the album, because I really wanted it to be a duet.”

California Girl

To have left it off would have been a huge mistake, as “San Francisco Blues” is one of the twin engines that pulls Crooked Tree together thematically. It’s an album grounded firmly in the place she grew up, but also one that longs for California’s past, and warns of how much more it can lose.

I miss the stars that used to shine and the days of ’49,” she sings. “But most of all I miss the California dreaming.” With its lyrics about gentrification and the displacement of artists, it’s a bittersweet tribute.

“I just love the San Francisco Bay Area so much,” says Tuttle. “I find myself writing a lot of songs inspired by California, because it’s where I grew up, and it’s always going to be home to me, but it does kind of make me sad because so many musicians and artists can’t live there anymore. I feel like the area has lost a lot of what has made it really special. Even when I was a kid in the ’90s and early 2000s, it felt like maybe there was more of a creative vibe, and certainly in my parents’ generation, the ’60s and ’70s, it was the counterculture movement of the country. I grew up hearing those stories, and have always felt a nostalgia for the San Francisco of old, but I still love the area so much. That’s why it’s kind of a love song to San Francisco, but also kind of a sad song.”

“Crooked Tree” is the other core of the record, a celebration of the misfit, the outsider, the outlaw that fuses all of Tuttle’s songwriting concerns and pulls the landscape of California into its lyrics in the most personal way possible. Oh, can’t you see/A crooked tree won’t fit into the mill machine?she sings.They’re left to grow wild and free/Oh, I’d rather be a crooked tree.”

It’s a title track that’s every bit as personal as it sounds. “That one for me is about just kind of learning to embrace my individuality,” says Tuttle. “I wrote it with Melody Walker, who’s also from the Bay Area, and we both grew up feeling different than other kids. I found out later that she grew up with scoliosis, and had to wear a back brace all through school. So the crooked tree is literally she kind of felt crooked, her back was not straight when she was a kid, and it made her stand out. And I lost my hair to alopecia when I was a kid, so I was always wearing hats, or I was the bald kid, or when I got to high school, I started wearing wigs. So it took me a long time to really embrace that part of myself, and feel comfortable with it.”

And it was natural, no pun intended, for the two women to use the forests they’d grown up around as a personal metaphor.

“We both love songwriters like Kate Walker and Laurie Lewis who write about the natural landscape of Northern California,” she says. “We were kind of inspired by them when we were writing that song.”

Tuttle’s love of the Bay Area even extended to her pandemic covers record from 2020, But I’d Rather Be With You, for which she chose to record not only the Grateful Dead’s “Standing on the Moon,” but also a gorgeous version of Rancid’s “Olympia, WA.”

“I used to play it with my friends when I was in middle school; we all love Rancid and Operation Ivy,” she says. “I think we were like a little bit young for that band. But my friend’s older siblings had gone to see them, and had their merch and stuff. We would steal my friend’s older sister’s Operation Ivy hoodie and feel really cool. And then like a couple years ago, I was playing in Olympia, Washington, and I was like, ‘Well, I have to play that Rancid song.’ It just kind of came back to me. When I went to do the covers record, it was one of the first ones I thought of, because it’s kind of showing the music that I grew up with, and I just love that song. I think it’s so cool.”

How She’s Grown

After her foray into covers with the 2020 album and its follow-up EP from last year, But I’d Rather Be With You, Too, Tuttle returns with her strongest songwriting yet on Crooked Tree. One person who’s seen her evolution firsthand is Santa Cruz musician AJ Lee, who played with her in the family band put together by Jack Tuttle. They actually met through the network of bluegrass players that came out of the NorCal festivals—Lee’s parents knew about Jack’s reputation as a teacher, and reached out to him. He was struck by her talent, and integrated her into a band that also included Molly, as well as his sons Michael and Sullivan Tuttle. There is a future documentary to be made about the sheer amount of Americana talent that came out of this one young band—and young is no understatement. Lee was eight or nine when she joined in the late 2000s, and the Tuttle kids were in their preteens and teens. In the somewhat awkward position of having a family band with one non-family member, Jack called it the Tuttles with AJ Lee. All of the members moved on in the mid-2010s after racking up a remarkable number of individual awards, but the bonds between members remained. Molly, for instance, played on Lee’s debut solo album, while Sullivan joined Lee’s band, AJ Lee and Blue Summit.

Along with covers and some of Jack’s tunes, the Tuttles with AJ Lee also played Molly’s first original songs, so few people are as qualified to chart her songwriting growth as Lee. And she says that while her songs have definitely evolved, they were always good.

“It was really cool seeing the progression of her songwriting,” says Lee. “But, I mean, even from the first songs that we did in the Tuttles with AJ Lee, they were fantastic songs.”

“I just loved harmonizing with her,” says Molly of performing with Lee. “She was just so talented from such an early age. She was a singing prodigy. That’s how I learned to sing harmony.”

Now on different ends of the country, they see each other when they can, but their solo careers keep them busy. “Every time I see Molly, and we sing together again, it’s just sort of like back in the old days, and it just feels so natural,” Lee says. “Even though we aren’t on the same projects anymore, it just feels so nice being able to have that history.”

Lee is also impressed with Tuttle’s new album, because she knows how hard it is to write in this particular genre. “Now I’m trying to write a little bit more fast bluegrass stuff, but bluegrass songs are really hard to write. So the fact that she’s made a whole bluegrass album is really incredible. Because it seems like it’s simple, but it is really hard to write something that is so simple, but so catchy.”

For Tuttle, making her first bluegrass album was a bit like coming home. “I remember thinking, ‘Well, I know what makes a good bluegrass song. I’ve grown up with the genre,’” she says. “And when I started writing the songs, I realized they were some of my more personal songs that I’d written, which surprised me because I’ve always felt like with bluegrass songs, I haven’t totally connected with the themes personally. Like, I didn’t grow up in the South. My dad grew up on a farm, but I grew up in Silicon Valley. So I never felt like I had a voice within the genre. But suddenly, it seemed like I found ways to make the songs still ring true to me and tell my story.”

Molly Tuttle and Golden Highway perform at 8pm on Thursday, April 28 at the Guild Theater, 949 El Camino Real in Menlo Park. Rachel Baiman opens. Tickets for the all-ages show (under 18 must be accompanied by parent or guardian) are $44 and up. guildtheatre.com.

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