Madison Cunningham | Artist to Watch – November 2025

Hometown: Escondido, CA

Why They’re WXPN Artist Of The Month:

In what feels like the early days of what is destined to be a long career, Madison Cunningham is already a Grammy-winning singer-songwriter and guitarist with a pretty impressive track record. Blending West Coast folk-rock with sharp lyricism and intricate musicianship, her previous work has been catching ears for the better part of a decade. But it’s her new LP, Ace, that feels like a true moment of an artist blossoming into who they’ve maybe been meaning to be the whole time.

As detailed in this revealing New York Times profile, the road to Ace wasn’t easy; divorce, a changing approach to spirituality, and all of the upheaval that both can bring wound up becoming part of Cunningham’s process. What came out of it all, however, is beautiful. Shifting from her signature guitar-driven sound to a more piano-focused style, much of Ace channels the lost Laurel Canyon, sad adventurer vibe of the late, great Judee Sill. And with a flute/clarinet/bass clarinet trio punctuating many of the arrangements, the record also has the light orchestral scope of some of Rufus Wainwright’s best stuff. The result is a lush, living record—one that captures an artist growing in real time, crafting songs that are both vulnerable and masterfully composed.

You Might Know Them From: After earning acclaim for Who Are You Now (2019) and winning Best Folk Album at the 2023 Grammys for Revealer, Cunningham took a 2024 detour to remake Lindsay and Stevie’s Buckingham/Nicks with Andrew Bird.

Fun Fact: One of Cunningham’s earliest breaks was as a cast member of American Public Media’s show Live from Here, the now-defunct spinoff of A Prairie Home Companion. 

Essential Tracks: “Wake (ft. Fleet Foxes),” “Break The Jaw”

Catch Them Live: Ardmore Music Hall on April 2, 2026, near the end of a US tour that follows a trek thru Europe early in the new year.