Photo by Jake Hurwitz
6 ‘5″ (you have to take his word for it) and covered in tattoos, when you first listen to Kai Wilson’s music, you don’t expect the honesty, rawness, and growl in his voice. “I’m fucking sad,” exclaimed Kai during our interview. Originally from New York, Kai has been playing around Boston for some time now — he’s played at Rockwood in Fenway, the Middle East, Club Passim, and even the Burren (all the local favorites). On Tuesday, February 6th, he’s playing a Breaking Sounds show at Bill’s Bar in Fenway, and you’ll get to hear his unique voice along with songs from his debut, unreleased album (coming soon).
Self-described as having “high energy, sad boi vibes” and “cowboy crying music,” Kai’s genre leans towards indie folk under the country umbrella. His musical influences include John Moreland, Jeffrey Martin, Zach Bryan, The Lumineers, and Mumford & Sons.
The album is called Old School Simple Love after the title track (did you guess it?) “Old School Simple Love.” The song was inspired by Kai’s parents, and how their marriage taught him what a marriage should entail: being a support system, making sacrifices, and understanding emotions.
Kai says this “vulnerable album speaks to the honesty of [his] emotions” and consists of 8 songs that he feels are honest and have been created in his own sound. Though Kai usually plays an acoustic guitar, this debut studio album has a full-band sound, including a fiddle and cello. It revolves around Kai’s experiences with relationships, as well as love lost and gained. “People use the word ‘love’ all the time about their family, friends, and significant others. But it takes a lot of bravery, courage, and hardship to be in love with someone.”
“I can’t stop singing songs, writing lyrics, and playing the guitar — It’s something I feel in my bones.”
Kai is someone who didn’t get involved in music in a ‘traditional’ way. His dad has been singing songs and playing the guitar since he was young, which inspired Kai to teach himself how to both play the guitar and sing recently. In fact, Kai and his dad played a show at Rockwood in Fenway together last year, and it was such a heartwarming moment to be a part of because Kai got his dad’s guitar fixed and surprised him by playing it.
Through Kai’s music, he wants people to feel like they’re not alone and that they have someone who is feeling similar emotions. Kai expressed that as someone who was raised as a man, showing emotions was equated with weakness. He felt like he couldn’t show his vulnerable side and that there was a stigma around asking for help. “I want people to know it’s okay to feel strongly, to struggle, to not be okay — it makes you more of a person,” stated Kai matter-of-factly.
Even in the making of this album, Kai has been an advocate for men’s mental health awareness. He ran a crowdfunding campaign for the album through the title track, and once he reached his goal, he donated the extra money to the American Foundation for Suicide Prevention. The song became something much bigger than his parents; it’s a song that everyone involved with Kai in some shape or form is now a part of.
In addition to promoting his own music and shows on social media, Kai also supports other artists in the music scene, including one of my favorite people Amanda Shea (their friendship makes me so happy)! Some artists he would like to collab with are Kayla Erhardt for her amazing vision of her songs, Ollella for her mesmerizing sound, and Sneaky Miles for their honest writing.
Some of Kai’s favorite lyrics from the album are from the title track, “Where we grow old with each other and we work on it together, where there’s no second-guessing kind of love.” The other lyrics he’s proud of writing are from a song that’s unreleased (!) called “You Won’t Find Him.” When he told me the lyrics, I was in awe of the sass and depth to the words. You’re not ready, but here you go: “But you won’t find him. No, not in me — I’m not the guy who hurt you. He’d regret meeting me.” SAD BOI vibes right there.
“Come to my fucking shows!” said Kai. Honestly, I agree — you’re missing out on cool merch (beer koozies and shirts) and songs that you feel in your heart and soul. If you want to experience Kai’s amazing scoops (I deemed his vocal scoops the best in 2023), along with his honest emotions, come out to Bill’s Bar on Tuesday, Feb 6th in Fenway and experience his sound for yourself!