Lola Leon Finds Her Way Back to Herself With “T Shirt”, Her Most Personal Song and Video Yet

“I can’t even tell you how important community is to me,” Lourdes “Lola” Leon says on a recent morning. “I would’ve been dead in a ditch if it wasn’t for my friends. Not to be dramatic, but that’s how it feels.”

No one—not even Leon, whose starry life as a musician and model began in 1996, when her mother, Madonna, birthed her—is immune to the scars a heartbreak leaves. But she also knows that a low point in life can become a source of inspiration. That’s the idea behind the Los Angeles-born, New York City-based artist’s latest single, “T Shirt,” which she released with a deeply personal and pared-back music video directed by cinematographer Eric Yue on May 27. The song, as Leon describes it, is “pretty straightforward. It’s nothing too metaphorical: you’re in the throes of an unhealthy love. And as a young person, I think we try to rationalize horrible things that happen, people’s shitty behavior.” The antidote to that kind of hurt, Leon has found, is in the people who love you most, those who have stuck around. As such, her close friends (like Sammy, her longtime producer who made “T Shirt” with Sega Bodega) and family members, including her paternal grandmother, make cameos in the video. “I wanted to capture the core of who I am,” Leon says of the concept. “And not in a way where it felt so put on. This is really my life.”

After putting out her debut EP in 2022, Go, under the moniker Lolahol, Leon says she was “struggling with my visual identity. I was in such a transitional period that I didn’t feel rooted in anything.” Not to mention, she was in “such a wrong relationship for so many reasons,” she says. “But I was trying to make it seem all right. I was poisoning myself, drinking so much. I remember my friends looking at me like, ‘What are you doing?’ I was so reliant on certain people around me. I was always calling my grandmother and crying.”

Leon explains that she knew she would heal, “in the back of my mind. There’s a quote in the song: ‘My heart will know, my head will follow.’ That was like a mantra I repeated to make myself not literally become fully 5150.” That feeling of hopefulness pervades the track and the video, which feels more personal than anything Leon has put out in the past. “When I first put out music, I was so scared, literally shaking,” she recalls. “At first, you’ve got to keep this fierce, cunt wall up in front of you, just in case you get hurt. But now I’m at a place where I feel comfortable to an extent sharing that part of myself.”

Leon, who turns thirty in the fall, says she’ll be releasing more music later this year under her own name, Lola Leon; the material will sound “introspective,” she explains, like “T Shirt.”

“People keep saying, ‘This is a new era, this is a new era’—I don’t know where that came from!” she adds with a laugh. “It’s more just about embracing my roots and tapping back in with people who’ve watched me grow over the years. I’m still Lola! Just no more ’hol’—we’re dropping the ’hol.’”