Here’s how Bob Dylan found Brittney Spencer

In 2020, Spencer worked at Warby Parker. Today, she’s your favorite musician’s favorite musician. 

And it’s not something she takes lightly. 

“I’ve learned so much from my time on the road with my favorite artists these last six years. It’s absolutely shaped me,” she says.

“Honestly, getting to play with so many of my heroes and icons — at some point I had to be like, ‘Girl, your imposter syndrome is not going to go away on its own. I don’t know who else you need to sing with. Do you need to sing with Jesus? Do you need to, like, go back in time and sing with Patsy Cline?’

“It’s silly not to believe in yourself when you have all these folks believing.”

With silky smooth vocals and a poet’s sensibility, Spencer will move you. Raised on gospel and R&B in Baltimore, the genre-blurring vocalist brings an R&B swagger to country tunes. 

Must-listens: “Bigger than the Song” — an ode to country radio stars, from Dolly to Johnny and June— and “Night In,” which flips the classic night-out, ode-to-the-barroom country song on its head.

For a crash-course, watch her Tiny Desk Concert. Her new single, “Sober Thoughts,” is out now — she says she’ll announce her upcoming album soon.

Ahead of her tour with Dylan — literally, I reach her as she’s packing at her Nashville home, clothes strewn on her bed — we talked Dylan, Bob Weir, Willie Nelson, Beyonce, growing up in Baltimore, how her badass great-grandpa was chased out of town, and more.

Boston.com: I saw the video you posted of Dylan watching you at Outlaw Fest —you said that’s how this all started.

Brittney Spencer: It did. I didn’t know til afterwards that Bob watched our set. A fan sent me the video. Then he went to my dressing room. He was incognito. He even had a hoodie on with the hood on, and it was 90-plus degrees outside.

[laughs] Classic.

And he was so cool. He was so nice. He asked if I sing around, asked for my number. I wrote it on the napkin. He never called me.

Then a few months ago, I emailed his tour manager: “Hey, if Bob’s in Nashville, I’d really love to see Bob again. He was talking about us getting together.” And I never heard back from him, either.  [laughs] 

[laughs] Even more classic. 

Then my agents got a call saying Bob wanted me to come on tour. As I talk to you right now, I’m packing. I have all my clothes scattered on my bed. I’m trying to figure out outfits, so I’m really excited. I haven’t seen him since Outlaw Fest.

I interviewed Lucinda Williams a few months ago — she also opened some dates with him this summer— and we were talking about your song on her new album, “World’s Gone Wrong.”

She’s so cool. I learned so much from her just from that.

In 2023, I think, they did a tribute for her at Americana Fest, and Grace Potter called me like, “Hey, come sing with me.” I flew in, and we sang [Williams’s song] “I Lost It” together. It was so cool.  Man, it’s just exciting to watch all these dots connect and watch the story unfold.

You do have so many dots. Grace Potter is from Vermont. You toured with her, too.

She brought me on the road in 2024 while I was in the middle of releasing my first album, “My Stupid Life.” 

She’s the best person, honestly, that I could’ve done that with. She’s one of my top three performers I’ve ever seen live. Her energy on stage is insane — I learned so much from her.

She is a master of the live act. And another big person who tapped you to work with them: Beyoncé. You’re on “Cowboy Carter.” How did that happen?

Oh man, I have no idea how this woman found out I exist. [laughs] 

[laughs]

All I know is I couldn’t say no. I couldn’t believe it. A lot of opportunities I’ve been given have helped me learn about myself as an artist and what I want to do and how I want to contribute to the world. I’ve learned so much from my time with my favorite artists. It’s absolutely shaped me.

I bet. And you just released a single, “Sober Thoughts.”

That’s a direct result of being on the road with people who know how to be themselves, unashamedly. They show up how they’re going to show up. I’ve learned so much from them, I just try to throw that into my music.

I can see that. So tell me about you. You said you grew up moving around Baltimore a lot. You’ve been singing since you were 4. What were you like as a kid?

I just wanted to sing all day. I felt things very deeply. That pushed me into songwriting as a teenager. I started listening to music that made me want to write.  

I took a few different turns, but it’s all leading to the road I hoped I’d be on when I was a kid. I’ve always wanted to be the person that I am right now. I’ve always wanted to be her.  So the fact that I get to be her — man, I couldn’t ask for anything more.

I love that. So what drew you to country music? You said you visited family in South Carolina every summer.

That was my introduction to the South. I fell in love with the culture. In my adult years, my grandmother told me she thinks that I have such a deep connection to the South because that’s where she’s from: Greensboro, North Carolina. 

Then she told me the coolest f—ing story. She said, “We ended up in Baltimore because my father got car-chased by the police out of North Carolina.” I was like, “What the hell?”

[laughs] 

She said, “He got car-chased out of town because he was a runner — he’d run moonshine. He knew how to work on cars, so he built his engine to go faster than the cops.”

Oh my God.

I was like, “Grandma, this sounds like a movie.” So basically, I ended up in Baltimore because my great-grandfather was police-chased out of town for selling moonshine. I’ve never been more proud of my family. 

[laughs] That’s one badass great-grandfather.

I know! Now we’re officially cool, thanks to great-grandpa Troy. 

[laughs] So, what did pull you into country music? I know you first heard The Chicks when you were 14.

The Chicks — that’s when the music and the culture started to connect in my brain. They sounded like church.  Then I fell in love with Taylor Swift and Shania and Reba and Brad Paisley. I love country music with all my heart. 

What do you love about it?

The storytelling. The instrumentation. I can’t describe what a pedal steel does for me internally.  There’s nothing like sitting with my guitar and just talking about how I feel.

What inspires your songwriting?

It could be a conversation with a friend, or something I hear in passing, or just wanting to get out of my own brain and write a story that has nothing to do with me.

I live by the motto: Listen to the poet. If you want to understand the world, listen to the poet. If you want to know what’s going on, if you want a moral compass, if you want a dose of real life, listen to the poets.

I love that. Speaking of poets: And are you a Dylan fan?

I love him. He’s a writer. I have no idea how accurate that movie [“A Complete Unknown”] is about him,  but there were moments where I was like, “He’s the coolest guy alive.”

[laughs] He is.

He makes me want to be more myself because he didn’t give a damn if you like it or not — he was gonna be himself.

I feel like you have a similar attitude.

Oh yeah. But I have to will myself to not care. [laughs]

[laughs] Going back: The first time I heard you, you were playing with Willie Nelson. Again, how did he find you? 

I have no idea. [laughs] I genuinely have no idea how any of this stuff happens, and I’m not bold enough to ask. I’m just thankful and try to be gracious when people bring me into their journey. And Willie is the best. He always brings everybody on stage for the last song — even the crew and their kids. He’s so sweet. He’s one of my favorites.

One group where we do know how they found you: The Highwomen retweeted you in 2020. Did everything change overnight?

My life changed immediately. They set off a domino effect. Now we’ve become family. I’m so excited: After I open for Bob Dylan in New Hampshire, we fly to Red Rocks because I’m opening for Maren Morris — she’s having the rest of The Highwomen as well. It’s a family reunion every time we get together.

Were you always driven to be a songwriter, or was there something else you were interested in?

As a kid, I wasn’t thinking about anything else. It’s absolute delusion and fixation. I’ve been hyper-fixated on a pulling in my soul. 

When I go to schools and talk to students, I say, “If you can do anything other than music, do that.” Music is insane. Releasing music right now is really hard. Artists are up against AI music. We’re up against a numbers machine. People don’t develop artists anymore. It’s a hard game. 

So I mean it when I tell students: “If you wake up every day and the only thing you want to do is sing or write, then do it. But if you think, I could be a doctor, you should do that.” If you cannot live without music, that’s when you should do it. But that’s me personally.

No, I think that’s a good bar for any creative field. To be honest, I was the same way with writing as a kid. A lot of creative people will feel you there. You have to be obsessed. 

There’s nothing else I can do. My soul is attached to this. If there was something else that I could do, I would. Because this industry is insane. But my soul is tethered here.

So when The Highwomen retweeted you, you were working at Warby Parker, and as a social media manager at a publishing company. 

But I had made a four-song EP. I had been sitting on it. When they reposted me, Billboard reached out to interview me, and they were like, “Oh wait, you have music? Can we exclusively release it?” I was like, “Uh, yeah.”

[laughs] Right.

Then gosh, all kinds of things happened: Maren mentioned my name at the CMAs. Mickey Guyton asked me to sing with her at the CMAs. Jason Isbell asked me to be on tour. It happened so fast.

You also played with Bob Weir a lot.

I miss him. The first time I met Bob was to sing with him at Radio City Music Hall. Then he just kept inviting me out. The biggest confidence booster has been how much these icons have believed in me. That’s why I’m thankful with this Dylan tour. I’m so thankful these icons believed in me because it forced me to start believing in myself.

Brittney Spencer, along with Jimmie Vaughan and The Tilt-A-Whirl Band, will open for Bob Dylan at Leader Bank Pavilion in Boston on Thursday, July 16, at 7 p.m. Limited tickets remain via Ticketmaster.

The interview has been edited and condensed. Lauren Daley is a freelance culture writer. She can be reached at [email protected]. She tweets @laurendaley1, and Instagrams at @laurendaley1. Read more stories on Facebook here.

Lauren Daley is a longtime culture journalist. As a regular contributor to Boston.com, she interviews A-list musicians, actors, authors and other major artists.

Sign up for the Today newsletter

Get everything you need to know to start your day, delivered right to your inbox every morning.