Best New Artist nominee Molly Tuttle, who started playing guitar at eight and attended Berklee School of Music, was the first woman to win the International Bluegrass Music Association’s Guitarist of the Year award. But the Cali native shows she’s equally adept as a songwriter, following her Tony Berg-produced 2020 covers LP …but I’d rather be with you with this year’s acclaimed Crooked Tree (her first for Nonesuch), which she co-produced with dobro icon Jerry Douglas. Largely co-written with Old Crow Medicine Show’s Ketch Secor, the LP features collabs with Margo Price, Billy Strings, Dan Tyminski and Gillian Welch. Tuttle’s BNA nom may have surprised the pop world, but the Nashville transplant is a musical connector.

Check out a flipbook of interviews with Best New Artist nominees from our Grammy Preview: Part 3.

You got one of the Big 4!
It’s super-exciting. It’s such an eclectic field and encompasses all the genres. For bluegrass, which is seen as a small genre, it’s especially rare. But it’s a very tight-knit community.

Your reach extends beyond traditional bluegrass, though.
When I got to Nashville, I wanted to explore other genres. I play flatpick guitar, so that’s a giveaway—and I take it with me everywhere.

Your “everywhere” is pretty vast.
Flatpicking a guitar with electronic sounds is really exciting. I was seeking something I hadn’t heard before. I can play really fast and complicated stuff, but often I’m playing it over really simple things.

That aspect really came out on ... but I’d rather be with you.
My generation grew up with access to all kinds of music; the things we were listening to were very different. Hazel Dickens’ “A Few Old Memories” was the first record I really fell in love with, but then Phoebe Bridgers’ Punisher is so good. I was punk as a kid, so I was into Rancid’s …And Out Come the Wolves. We made the record during the pandemic, me doing my vocals and guitar parts alone in my house, then sending to Tony. We wanted to strike a balance, not have an obvious song, something a little left field from the original. His philosophy really stressed having a central meaning and saying things you mean.

Did that carry over to your writing for Crooked Tree?
I started out as a musician, but lyrics and melody cut through everything. With this record, I had much more to say. I went to my grandfather’s farm, which isn’t in the family anymore and is run-down, and that’s where it all started for me—one song led to another. I’m from that three- or four-chord school because I grew up playing folk songs, really simple things.

You shred as a player, yet you simplify as a writer.
I feel like I have two brains: my songwriter brain that works sitting and strumming, and my musician brain. I always think about writing in a way that goes back to when you write an essay in high school. You have a thesis, which is the hook, and every paragraph supports it with new information. So when you get to that last chorus, it all opens up into something more—and how you play it...

That’s where Jerry Douglas and those players come in.
I played on Bela Fleck’s My Bluegrass Heart, and it really inspired me. Jerry was receptive to my ideas. It’s so fun having that spirit of community, having my list of dream musicians there. We tracked live after two days of preproduction: four days of all of us in the studio together. We were coming out of the pandemic; people were starting to do shows, so I knew we had to do this quick.

You got the title Crooked Tree from something Tom Waits said, right?
It’s a line from a show he was in, a metaphor a friend of mine saw in a clip online. I wish he’d said, “Molly, you should be a crooked tree”; that would’ve been awesome. I’ve never met Tom Waits, but I’d love to.