Last November, singer-songwriter Madison Cunningham released a four-track EP titled “Wednesday” consisting of covers – John Mayer, Radiohead, Tom Waits and The Beatles. While some fans may have been hoping for a sequel to her 2019 debut, “Who Are You Now” – for which she received a Grammy name for Best American Album – the multi-genre artist said she wanted broadcast something to listeners “already knew,” hoping that a taste of nostalgia can bring comfort during the pandemic. (The concept also originated from Cunningham Weekly Wednesday Covers series on his YouTube channel.)

In February, Cunningham, 25, released his new single, “Broken Harvest,” a shimmering symphonic act of resilience as part of NPR Morning Edition Song Project. She will bring her harmonic and hypnotic blend of western folk, blues and rock to the Sinclair on October 25 – just days before it opens for Harry Styles’ rescheduled shows “Harryween Fancy Dress Party” at Madison Square Garden on October 30 and 31. . . We spoke to Cunningham in September about his quiet life on the West Coast over the past year, and this time Styles has crept into his DMs.

What do you think has influenced your creative process the most over the past year? And do you think there is something specific that you want to describe in your last composition?

It was hard to find creativity on top of the world falling apart and what seemed to be ending. At first, I was ashamed of not seizing the moment better. But then, it’s really hard to create from a rocky place. Even though many of our subjects are written about the difficult times in our lives, as artists it is easier to write in retrospect.

What eventually inspired me were the limitations we faced. It was like trying to draw with your left hand, if you are right handed. And then I lost a loved one in the middle of last year, and it shrunk everything into a lock-sized hole, where I could just see through that experience. I felt like I could then write from a place of grief that was mine, and it wasn’t just second hand and watching what was going on around me.

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

Definitely – my reasoning behind releasing a cover EP was that releasing anything that had lyrics or anything that wasn’t written in 2020 felt insensitive to me. I struggled to write for a few months, so I started singing other people’s songs. “The Age of Worry” was a nostalgic song for me, and seemed incredibly relevant to me at the moment. It was a song from the past that spoke to the future.

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

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

I’ve never performed my own show in Boston, so I’m really excited to have a firmer memory there.

How did the opportunity with Harry come about?

Before it all ended in February 2020, I was finishing a tour and opened up Instagram and got a message from him. I thought it was a fake at first. He would say that he was shown my record, I guess, and was like, ‘Yeah, I’d love to go online at some point. I really like.’ Finally, he said, “Would you just open up for me for a while?” Super unexpected thing. But apparently he was listening to my music for he got robbed last year in London.

I remember hearing about this story.

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

This interview has been edited and condensed for clarity.

MADISON CUNNINGHAM

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

Madison E. Goldberg is a Boston-based reporter. You can reach her at [email protected], or follow her on Twitter @madisonevegold.