“It saved my life, for sure… I don’t know how people survive without writing songs. I don’t know how to process anything without it,” says Kelsey Wilson, frontwoman and bandleader of Austin soul/funk/R&B outfit Sir Woman (also of Americana band Wild Child). This February, Sir Woman released If It All Works Out, the follow-up to 2022’s self-titled debut LP, and the first half of a double album, which will conclude with If It Doesn’t, set to drop in the very near future. The music was born out of a series of tragedies, with Wilson’s father passing away between the making of the first full-length and follow-up, and the loss of her sister while recording If It All Works Out, leading to the decision to create a two-part album, joking that If It All Works Out is the album for a good day, while If It Doesn’t is an album for a bad day. However, she says she’s very proud of both parts of the album and that they embody the same vibe and spirit of Sir Woman’s debut: “This is my favorite record I’ve ever done… I’d say they still hold onto the positive, self-love, empowering message.”
The last time I spoke to Kelsey Wilson was in September of 2022, prior to Sir Woman’s first appearance in the City of Brotherly Love and Sisterly Affection, a headlining show at The Lounge at World Café Live. This time around, we’re chatting between legs of the Album Release Tour, which resumed about a week and a half ago and will have Sir Woman headlining Johnny Brenda’s (which she’s played with Wild Child and apparently loves!) this Tuesday, May 6th. “The biggest highlight has been everybody singing all of the new songs! I mean, when we went out, the album had been out for like a week!” Wilson tells me of the first leg of the tour. But she also says, on a more serious note, that singing these songs she wrote while processing so much grief has been helping her continue to deal with her emotions: “Having to sing them every day is helping me feel what I need to feel every day.” She even goes on to joke, “Ultimately, we’re all gonna lose everybody [laughs]… I get to share my experience and maybe help people going through something similar.”
This past October, Sir Woman spent some time on the road opening for our good buddies Sammy Rae & The Friends, who Wilson tells me proved to be the perfect pairing: “I don’t think there’s ever been an easier fit, personality-wise, band-wise with them… They’re all so talented and we definitely share the same energy in trying to cultivate positive vibes and energy everywhere we go.” And, like I learned during my most recent chat with Sammy Rae, Kelsey tells me that Sir Woman’s debut, similarly, came prior to the formation of the actual group: “When I made the first album, I didn’t have a band. I was just throwin’ shit against the wall… I was like, ‘I need to get these songs out of my head, just so I can!’”
However, Kelsey also admits that Sir Woman’s lineup has changed quite a bit since 2022: “You won’t see any of those players from the World Café Live show on this tour, although the singers will be the same; they never change… I have lost some players. When it comes to artists like Erykah Badu, Lauryn Hill, Jon Batiste, there’s no way I can compete.” But she also tells me that fans rarely seem to spot the changes: “I thought the audience would notice that the drummer is different, but nope!” Wilson says that what all of the lineups she’s performed and recorded with have in common is that they’re all amazing players (referring to them, “like tools in a toolbox”) and there’s always a shared love and respect: “I love to run a band like a family. I want it to feel like a family road trip on every tour… We love each other, like a family, we fight sometimes, like a family.” And, in addition to the lineup changes, Wilson says that the live show is forever changing.
“No one will ever see the same Sir Woman show twice. Like, I have no idea what this upcoming run is gonna be like… Honestly, I have no idea what it’s going to be. Until we start playing the first song, I’m not even gonna make the call, and it drives my band crazy… When we walk out, I’ll make the call right then when I look out and see the audience.”
If It Doesn’t – which features previously released singles “Miss Connection (Ft. Trinidad James)” and “Believe It Or Not” — is set to drop May 16th, but Kelsey tells me that there’s already new-new music in the works: “I’m really excited to start working on another record… I’m obviously really excited for the second half of this to come out, but when I release something, I feel all this energetic space in my heart and my head and songs just start coming out.” She also says that, with the band getting bigger and bigger (The tour featured sold-out shows in San Francisco, Portland, Denver, and Cambridge, and even multiple nights in Chicago and Washington DC, after one night sold out.), her ability to hold onto her lineup is getting better and better: “As the music gets bigger and bigger, I’m better able to take care of them…”
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