Awash in a lush blue light and wearing a flowing sapphire dress, Madison Cunningham gracefully took a seat on stage at the Wilbur Theatre on Saturday night. If the stage — outfitted with rocks, reeds, and moss — had become a riverbed, then Cunningham herself was the river.
Cunningham and her multi-instrumentalist sideman, Jesse Chandler, faced each other amid the greenery as they commenced the night with “Shatter Into Form I,” the first interlude from Cunningham’s latest jazz-infused folk-pop album, “Ace.”
The stage plot was designed to mimic the Los Angeles River Trail Cunningham lives near. The bird noises that played in between songs were also collected at her home in LA.
“I was walking the trail every day, and that environment felt like the record to me as well, or the background of the record,” she said in an interview with The Beacon, a few hours before showtime. “[Chandler and I have] recreated a lot of the sounds with just us two, which has been really, really exciting and hard.”
Cunningham has been making music since 2017, making her major label debut in 2019 and winning her first Grammy nomination. In 2022, she won the Best Folk Album Grammy for her second full length project, “Revealer.” In 2025, she released “Ace,” her most experimental yet.
The instrumental depth of “Ace” is thoughtfully distinctive. Woodwinds, keys, and guitar layer together to produce Cunningham’s chamber-like sound. It all came together once Chandler joined the recording of the album in the fall of 2024 in Woodstock, N.Y., Cunningham said.
“I wanted the world building to feel really specific. We kind of just figured it out as we went,” she said. “I had a hunch, and then we just followed it. There was one song that we recorded, that was without woodwinds, and it felt wrong. We ended up adding them, and it just became a staple of the sound of the record.”
Cunningham knew that her live performance had to include the same engrossing instrumentation. That’s why Chandler is responsible for four different instruments: he juggles clarinet, bass clarinet, and the flute, often while simultaneously playing the mellotron. Cunningham wasn’t slacking either — she switched between keyboard and two different guitars in alternate tunings.
Cunningham recalled visuals of leaves falling as she was working on “Ace.” Although it’s inspired by the season, the album’s twinkling melodies and introspective lyrics make it viable for any season or state of mind.
“There’s a lot of discovery and a feeling of dying, but then coming back to life,” she said. “I feel like it’s been no mistake that we’ve been performing all of these songs during this time, because it’s feels like it matches the season.”
One of the most striking moments on the record comes near its end. Throughout the first 12 tracks, the sophisticated instrumentation builds as Cunningham sings about untangling herself from a past relationship in a nuanced and self-reflective manner. “Goodwill” and “Best of Us,” the final songs on the album, also closed out the show.
With “Goodwill” the Wilbur turned into a sound bath, and the audience seemed to enter a meditative state. Not as a calming sonic wash, but an all encompassing and dense sensory experience.
“‘Goodwill’ is about continuing to have this faith in someone that has continuously let you down and how love kind of does that, it believes the best in people,” she said. “I felt like it was almost the last part in me that needed to let a piece of someone go. And it felt very cathartic and I was kind of angry and I love when songs justify your anger. It’s so exciting.”
Then on “Best of Us,” Cunningham says exactly what she wanted to all along. A final goodbye of sorts.
“It slows down and it says everything very clearly that I was hoping that the other parts of the record were clawing at,” she said. “Like, who gave up first depends on who you’re asking. That to me was a big, big linchpin for the record, lyrically.”
Cunningham may have played her “Ace” with this record — her heaviest and most challenging yet — but as the tour wraps up, she is nervously welcoming everything that awaits her.
“There’s always a fear phase where you’re like, ‘I don’t know if I know how to do this,’” she said. “So that’s where I’m at right now. And I’m really excited for it to reveal itself to me. I think it’s just going to be a journey.”
She added that her artistic process has evolved as she has grown as a musician and songwriter.
“Some match will strike and you’ll be like, ‘Oh my God, I have this whole bank of ideas,’” she said. “If you don’t trust that it will all work out and you’ll find the right chorus or the right thing to say, then all you have to write with is anxiety.”
