V Girls: Olivia O’Brien

The LA-based songstress is no stranger to the spotlight. In conversation with V, the “Josslyn” singer details her viral rise, lyrical inspiration, and sonic path forward

This feature appears in V137, now available for purchase

In a year as uncertain as 2020, one current was always beyond doubt: Gen Z’s passion for the latest TikTok trend, challenge, and must-know dance. During a period brimming with confusion and turmoil, society found solace in a realm of unique virtual connection the platform offers.

Olivia wears all clothing and earrings Moschino, Bracelet Tiffany & Co. On eyes Nars Hardwired Eyeshadow in Goa

Leading the sounds—and kitschy dances—dominating the app’s bustling For You Page was singer-songwriter Olivia O’Brien’s snappy breakup track “Josslyn.” Charting a relationship turned sour, the anthem has amassed over 100 million streams and an impressive 75 million hashtags on the platform. “I was super excited about ‘Josslyn’ and I went for it. TikTok was happening then because we were all stuck in our houses,” O’Brien tells V. “That’s pretty much all we did—go on TikTok and try all the trends. It was divine timing, honestly.”

Backtrack a few years and O’Brien, then 16, skyrocketed to stardom with the release of “i hate u, i love u,” a heartfelt piano ballad made in collaboration with producer and rapper Gnash. O’Brien’s flair for storytelling was on full display throughout, a knack the singer carried since childhood when she would soak in the sounds of musicians like India.Arie, Michelle Branch, and Amy Winehouse.

Olivia wears all clothing and earrings Moschino, Bracelet Tiffany & Co. On eyes Nars Hardwired Eyeshadow in Goa

Growing up in Napa Valley, California, the songstress attended Catholic school for much of her childhood, a locale where she felt unaccepted and taunted for her passions. Now 22, O’Brien is coming into her own as an artist, channeling relationships, heartbreak, friendships, and everything in between into animated lyrics and melodies that vary in sound from pop-perfection to slow-tempo R&B. “My inspiration, which also is probably a terribly unhealthy thing, is my life” the singer says. “I’m most inspired when I’m sad or going through a breakup. I’ve always been a writer at the end of the day.”

After a successful debut album —Was It Even Real?—an unforgettable first-time Coachella performance, and a host of catchy singles to boast, O’Brien is charting her own path one snappy lyric at a time. While the singer’s sophomore album has been on pause, O’Brien has released an upbeat pair of singles—“Bitches These Days” and “Caught Up”—and unveiled the collaborative track “Bitch Back” with pop singer FLETCHER. “I’ve grown up as a person, writer, [and] artist. I’ve learned more about myself, been inspired, my sound has changed nonstop. I  never want to put myself in a box.”

This feature appears in V137, now available for purchase

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