“As my first headlining tour, I set manageable expectations, but I’ve been utterly blown away,” says Madison Cunningham. She’s chatting with me over the phone, en route to her next gig. Although just on her first headlining tour, the folk-pop singer/songwriter already has a laundry list of achievements of her young career (She turns 25 later this week.), including tours supporting heavy-hitters like Iron & Wine and Andrew Bird, and a Grammy nomination for best Americana album for her sophomore LP, 2019’s Who Are You Now.
Growing up in Orange County, the oldest of five sisters, with a pastor father, Cunningham’s earliest experiences with music began at age 7, when she started playing guitar in the church band. However, her teen years saw her expanding her influences to the greats, like Bob Dylan and Joni Mitchell, and her Spotify Playlists show her taste for the likes of Sufjan Stevens, Led Zeppelin, and Fiona Apple. Throughout 2019 and 2020 she even had a Weekly Covers series on YouTube, which featured her own renditions of her favorite songs by artists as diverse as John Prine, The Beach Boys, Elliott Smith, The Velvet Underground, and Talk Talk.
Madison Cunningham will be bringing her headlining tour to our very own Johnny Brenda’s on Sunday, October 24th, and while the show is yet to sell out, she tells me that many of the dates have been, so you may want to get your tickets soon: “Post pandemic, I didn’t quite know what we were walking into, but it’s been totally surreal, and the rooms have been full… Most rooms have known the lyrics and sing them so loud that I could walk off the stage and just let them sing.” She tells me that the performance is going to be a mix of songs from Who Are You Now and new songs that she composed during the pandemic.
In addition to her headlining dates, Madison Cunningham will be playing a couple super special, super-sized shows at the end of the month when she and Orville Peck provide support for Harry Styles’ Harryween Fancy Dress Party on October 30th and 31st at Madison Square Garden, a venue that she’s geeked-out over getting the chance to play her whole life. Although, while she says she is always thrilled to share larger stages with artists that she admires, she’s starting to get used to playing for her own crowds: “I love opening. I’ve had the privilege to open for so many of my favorite artists, but you’re playing for their crowd and you have something to prove, as opposed to having your own audience.” And when I ask her what some of the highlights of her career have been, she tells me the biggest one is actually happening as we speak: “I feel like I’m living one of the highlights right now with this headlining tour phase. It’s been so much fun. So many moments, too many to count, feel surreal.”