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Singer-songwriter Madison Cunningham.
Singer-songwriter Madison Cunningham.Claire Marie Vogel

Last November, singer-songwriter Madison Cunningham released a four-track EP titled “Wednesday” composed of covers — John Mayer, Radiohead, Tom Waits, and the Beatles. While some fans may have been hoping for a follow-up to her 2019 debut, “Who Are You Now” — for which she received a Grammy nom for Best Americana Album — the multi-genre artist said she wanted to put out something listeners “were already familiar with,” hoping a taste of nostalgia could bring comfort during the pandemic. (The concept also sprung from Cunningham’s Weekly Wednesday Covers series on her YouTube channel.)

This February, Cunningham, 25, released a new single of her own, “Broken Harvest,” a shimmering symphonic act of resilience as part of NPR’s Morning Edition Song Project. She will bring her harmonic and hypnotic blend of Western folk, blues, and rock to the Sinclair on Oct. 25 — just days before she opens for Harry Styles’s rescheduled “Harryween Fancy Dress Party” shows at Madison Square Garden on Oct. 30-31. We spoke to Cunningham in September about her quiet life on the West Coast during the past year, and that time Styles slid into her DMs.


What would you say has influenced your creative process the most this past year? And do you feel that there’s anything specific that you aim to depict in your latest songwriting?

It was hard to find creativity on top of the world crumbling, and what felt like it was ending. At first I was ashamed of myself for not seizing the moment better. But then, it’s really hard to create from a rocky place. Even though a lot of our subject matter is written about rocky times in our life, as artists, it’s easier to write about in retrospect.

What ended up inspiring me was the limitations that we were faced with. It was like trying to draw with your left hand, if you’re righthanded. And then, I lost a loved one in the middle of last year, and that just shrunk everything into a lock-size hole, where I could just see through that experience. I felt like I could then write from a place of grief that was my own, and it wasn’t just secondhand and watching what was happening around me.


You covered John Mayer’s 2012 track “The Age of Worry” as part of the “Wednesday” EP. On it, you leaned into nostalgia and brought in folk influences. Was that impacted by the experience that you mentioned?

Certainly — my reasoning behind releasing an EP of covers was that releasing anything with lyrics or anything that wasn’t written in 2020 just felt insensitive. I was struggling to write for a couple of months, so I started singing other people’s songs. “The Age of Worry” was a nostalgic song for me, and just felt incredibly relevant to the moment. It was a song from the past that was speaking to the future.

You’re playing at the Sinclair this time, but when was the last time you played in Boston?

I played there back in 2018, opening for the Punch Brothers, and I did another show with Andrew Bird (in 2019).

I’ve never played my own show in Boston so I’m really excited to make a more firm memory there.


How did the opportunity with Harry come to be?

Before everything shut down in February 2020, I was wrapping up a tour and I opened up Instagram, and got a message from him. I thought it had been fake at first. He was saying he had been shown my record, I guess, and was like, ‘Yeah, I would love to connect at some point. I really love it.’ Eventually he said, ‘Would you just open for me some time?’ Super unexpected thing. But apparently he was listening to my music while he got robbed last year in London.

I remember hearing about that story.

They stole his wallet and stuff. Apparently, he was listening to one of my songs and didn’t hear them approach him. So I feel a little bad about that. I feel like I’ve got to pay him back or something.

This interview has been edited and condensed for clarity.


At the Sinclair, 52 Church St., Cambridge. Oct. 25 at 8 p.m. $20. 617-547-5200. 18+ boweryboston.com

Madison E. Goldberg is a journalist based out of Boston. You can reach her at madisonevegoldberg@gmail.com, or follow her on Twitter @madisonevegold.