Molly Tuttle dishes on deluxe ‘Crooked Tree’ album, Grammy nod for Best New Artist

Hear our full conversation on my podcast “Beyond the Fame.”

WTOP's Jason Fraley chats with Best New Artist nominee Molly Tuttle (Part 1)

Molly Tuttle hoped that she’d compete for Best Bluegrass Album at the Grammys next February, but she had no idea that she’d also vie for the overall prize of Best New Artist.

“I woke up like, ‘Oh my gosh, it’s Grammy nomination day!'” Tuttle told WTOP. “People were texting me congrats. We saw ‘Bluegrass Album’ and were like, ‘Great! We got it!’ … Then, I wasn’t really paying attention anymore and suddenly I got a new wave of text messages in all caps like, ‘HOLY CRAP.’ … We saw Best New Artist. It was surreal.”

Her family and friends can’t wait to see if she actually wins in February, but first, Tuttle is stocking stuffings with the deluxe version of her acclaimed album “Crooked Tree.”

“We had our album release show in April where we played The Station Inn, which is kind of a historic venue here in Nashville for bluegrass,” Tuttle said. “We recorded the whole show and had [lap-steel legend] Jerry Douglas sit in as a special guest, my dad even came and played with us, so we took two tracks from that release show and put it in with the album.”

The deluxe album features those live recordings of “Dooley’s Farm” and “Catilleja,” as well as two brand new covers of The Grateful Dead with “Cold Rain and Snow” and “Dire Wolf.” The song selections provide a fascinating window into her family’s musical influences.

Born in Santa Clara, California in 1993, Tuttle grew up in Palo Alto performing with her family. At age 13, she released an album of duets with her dad Jack, “The Old Apple Tree” (2006). A few years later, she formed The Tuttles with siblings Sullivan (guitar) and Michael (mandolin), along with musician AJ Lee for the album “Introducing the Tuttles” (2011).

“My grandfather played banjo and loved bluegrass, so my dad learned from his dad,” Tuttle said. “After he finished college, he didn’t want to stay on the [Illinois] farm, so he moved to California where there was this great music scene in the Bay Area. … My dad started teaching banjo, guitar, all the bluegrass instruments. … He taught me how to play.”

While at Berkeley College of Music in Boston, she joined the all-female bluegrass group The Goodbye Girls. In 2015, she moved to Nashville with Billy Strings as a roommate.

“He was a great roommate, but his career was already exploding and he had more and more boxes of Billy Strings merch filling up the house, so after a while, he had to get a bigger place,” Tuttle said. “We had neighbors who were musicians too. Lindsay Lou had a big house where she would host jam sessions and house concerts. It was so much fun.”

While crowdfunding her first seven-track EP, “Rise” (2017), Tuttle became the first woman to win Guitar Player of the Year by the International Bluegrass Music Association. The next year, she won Instrumentalist of the Year by the Americana Music Association before signing with Compass Records for her first full-length album, “When You’re Ready” (2019).

“My first EP was all of the songs that I’d written since I started writing songs when I was 15, I had many years to collect those songs and pick the best ones,” Tuttle said. “‘When You’re Ready’ was songs that I’d written just since Nashville. … That felt like my first real album where we went into a real studio, it was a full-length record, it was so exciting.”

She followed up with the album ‘but I’d rather be with you again” (2020), including covers of The National’s “Fake Empire,” Rancid’s “Olympia, WA,” Grateful Dead’s “Standing on the Moon,” The Rolling Stones’ “She’s a Rainbow” and Cat Stevens’ “How Can I Tell You.”

“That came out of the pandemic, we did it all quarantine style, so I was learning to record my own parts in my house, then I sent them to Tony Berg in L.A., he produced them, got people to play on the tracks in their home studios,” Tuttle said. “It was all covers, so that was an exploration for me, picking songs that people might not expect from me.”

In 2021, Tuttle collaborated on three tracks for Béla Fleck’s acclaimed album “My Bluegrass Heart,” which won the Grammy for Best Bluegrass Album earlier this year.

“It was such an honor,” Tuttle said. “It was scary though. He writes such complex songs, I’ve been a huge fan of his music for a long time. He’s such a big hero and legend on the banjo that it’s hard not to feel intimidated. … I had to keep reminding myself: Béla knows what I sound like, he wouldn’t ask me to play if he didn’t want it to sound like me.”

The favors flipped as Billy Strings and Old Crow Medicine Show guested on her latest album, the aforementioned “Crooked Tree” (2022). It’s an album filled with great songs, but the lyrics of the title track is the most personal: “Oh, can’t you see? A crooked tree won’t fit into the mill machine. They’re left to grow wild and free. Oh, I’d rather be a crooked tree.”

“I developed alopecia areata when I was 3 years old, lost all my hair, it never grew back, I’m still completely bald,” Tuttle said. “I started wearing wigs when I was a teenager, but it took me years to accept that part of myself and open up about it. … It actually made me a way stronger person and have a lot more empathy and be someone who can help others.”

Does she have any advice for all of the other “crooked trees” out there?

“Hang in there,” Tuttle said. “I think everyone has something that makes them a crooked tree. It’s all about just being who you are and letting your freak flag fly when you need to.”

WTOP's Jason Fraley chats with Best New Artist nominee Molly Tuttle (Part 2)

Hear our full conversation on my podcast “Beyond the Fame.”

Jason Fraley

Hailed by The Washington Post for “his savantlike ability to name every Best Picture winner in history," Jason Fraley began at WTOP as Morning Drive Writer in 2008, film critic in 2011 and Entertainment Editor in 2014, providing daily arts coverage on-air and online.

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