INTERVIEW: Madison Cunningham

Madison Cunningham is constantly reinventing herself. Always looking for a challenge, the Grammy-winner is currently on tour promoting her powerful and transformative new album ‘Ace.‘ The album was born out of her young marriage falling apart, but is just as much about transformation as it is heartbreak, simultaneously celebratory and heart-wrenching, all while being raw and honest. She spoke with Cleverock about all of this and more from her front porch on a rainy California day during a brief respite from her world tour.

“I had two songs that I felt were the building blocks to a very specific world that ended up becoming that record,” she said. “[I] was going through a lot of upheaval in my personal life. So those songs were just on their own for six or seven, maybe even eight months. I was making another record at the time with Andrew Bird.” That record is, of course, the amazing 2024 cover of the Stevie Nicks, Lindsey Buckingham album.

“So, I kind of put all my attention into that and had a really hard time writing and focusing, and all the songs ended up coming two months before we were set to record. I was getting worried. I was starting to tell the producer I was working with that I don’t know how this is gonna pan out. We’ll see what happens.” She continued, “And then this basket of songs came out of nowhere. I say that not to sound cheesy or woo-woo or something, but that’s never happened to me in my life. It felt really spiritual… And that’s how making the record felt, too. I just surrounded myself with my really close collaborators and people that I’d been on the road with, and this wonderful multi-instrumentalist, Jesse Chandler, who plays all the woodwinds. Then, all the other crazy stuff, like mellotron and sub bass, and we really went for it.”

Madison has a long history of collaborations, recently including artists from Fleet Foxes and Deep Sea Diver. Rather than tour with a full band, though, it’s Cunningham and Jesse Chandler on this tour. “We decided to keep it a duo,” she said. “He is playing almost every woodwind you can think of. I love working with Jesse. I started to feel like that would be a different offering. This has been its own creative imprint and challenge. He’s just as good of a musician as it gets and is such a good sport.”

One standout element of ‘Ace‘ is the arrangements, particularly the strings and woodwinds, which add an upbeat layer to the songs. Even with these elements, Cunningham considers it without a doubt a breakup album. “I don’t think it could be anything else,” she laughed.

But was the dichotomy between the playful tone and the album’s raw subject matter intentional?

“It was as intentional as it as it could have been,” Cunningham explained. “Then the stuff that happens on top of that is the stuff you don’t plan for, the spiritual stuff. I don’t think I had the words to say at the time, ‘I would like to make a marriage between really thorny heartbreak and then the beauty that grows out of that,’ which to me would be the woodwinds and the strings. That is how I view this record. I knew I wanted that to be the world, but I didn’t know that that was the purpose it was going to serve, providing this counterweight.”

Ace is packed front to back with powerful, complex lyrics. The central motif might be one of breaking and reforming, as made evident in songs like “Shatter into Form” I and II, among others. When asked about that idea, she said:

“The guiding light in my personal life was trusting that all of that being broken open was going to, hopefully, lead to a new chapter and a new shape and a new reality. And that happened even just through the record. Just the ability to be able to kind of memorialize that time in that way felt like a death. You’re sending off a part of you. You’re releasing it. But I’ve learned for myself that releasing a piece of music is not the same thing as actually letting it go. I feel like this whole process of mixing, mastering it, releasing it, I’ve just had to let it go over and over again, and that’s its own chapter. But then touring it brings you into a completely different space of how do I engage with this now? It’s been beautiful.”

What about going too far when writing a breakup album, with the inherently painful and personal nature of it? “When the songs were being written, I had people in my life who I would send them to and be like, this isn’t too much, is it? But I think there’s a fine line. You have to be willing to be a little bit too much. Although I’ve been in this place of constantly asking myself, have I given too much or too little? I don’t know that I’ve walked away from this feeling completely certain about what the offering is, other than I got something off of my chest in a particular way, and sometimes that hangs in the air triumphantly, and sometimes that hangs in the air with a big question mark, that maybe that was a little bit too much of myself to show. But, you know, it is what it is.”

One thing is for sure: this album is a departure from her previous work.

“Completely,” she said, without hesitation. “It was a choice, I think, to not feel the pressures of creating a certain kind of record. Those voices have always been there, whether they’re from me or from actual outward pressure. And it felt so wonderful to be like, this is not an electric guitar record. I’m playing piano, because I love it… I’m not trying to fool anyone. I’m not trying to be cheeky. I love this. I just wanna make things that that I love. And not that I haven’t loved what I made in the beginning. I felt like I was using a lot of flashlights at the beginning, to look into the dark and be like, where am I going? Who am I? What am I? This felt a little bit more like this is who I am. This is the time and place. And I like that part of it. It felt really good and continues to feel really good.”

Before we parted ways, we had to talk about her recent appearance on comedy legend Tim Heidecker’s podcast, Office Hours Live, where Cunningham, Heidecker, Drew Erickson, and Jon Wurster live-arranged a holiday song telling Tiny Tim to quit bitching and to give Scrooge a break.

“I hope he releases that. He killed that,” she said, laughing. Asked about how the unlikely pair ended up playing together, she said “He is really good friends with someone who played in my band for a couple weeks.” So, they all ended up playing the same venue on the same night.

“After I played that night, he was like, wait, is this record out? Like, can I hear this? And I just ended up sending him Ace before it was out, and then I was on the podcast a few months later. So much fun… He’s so fucking talented but also the best.”

Heidecker also gave high praise for Ace, calling it the best album of the year, joining the essentially universal praise the album has received since its release. Rightfully so.