Six Degrees of Olivia O’Brien: Discovering Maya Donovan on the PIXIE Tour
A few weeks ago on October 6, 2026, I had the opportunity to cover Olivia O’Brien’s PIXIE Tour at Irving Plaza in New York City, with Maya Donovan opening the show. I’ve spent the past few weeks trying to gather my thoughts on the night because Olivia, as you might remember from my review of Benson Boone this summer, is one of my all-time favorite artists. When an artist has been part of your life for over a decade, seeing them live is one thing. Watching them continue to introduce you to new music and new artists is another.
Olivia has a habit of doing exactly that.
They say everyone in the world is connected through six degrees of separation. Either the theory holds up, or the music industry is a lot smaller than we think. In my experience, both might be true, because somehow, all roads lead back to Olivia O’Brien.
It started with gnash and their breakthrough collaboration, “i hate u, i love u,” which introduced me to an entirely new corner of pop music, sparking my love for discovering artists before they make it big. I discovered UPSAHL when she opened for Olivia just as the world was beginning to emerge from the pandemic. There was also FLETCHER, whose connection to Olivia through “Bitch Back” added yet another link to an ever-growing chain of artists, collaborations, and musical discoveries.
But the connections don't always stop with the artists themselves. Even some of the musicians sharing the stage have crossed paths with my own musical interests. I already knew Olivia's drummer, superflirt, through his own artist project, while guitarist Lilly Graves was familiar to me from seeing her perform with Maude Latour. It's a reminder of just how interconnected the music scene can be, especially when you spend as much time discovering artists and attending live shows as I do.
Each connection seems to lead to another, and before I know it, I'm following an entirely new artist I might never have discovered otherwise.
Maya Donovan is the latest name on that list.
An up-and-coming artist based in Brooklyn, Maya took the stage as the opener for Olivia's PIXIE Tour, introducing herself to a room full of fans who had come to celebrate one of sad pop music's most distinctive voices. For me, however, the evening began with the excitement of discovering someone new - and the question of whether Maya would become another artist whose music I'd continue following long after the show ended.
Maya Donovan's set brought an intimate, singer-songwriter atmosphere to Irving Plaza. The stage featured patches of greenery and flowers, creating an organic backdrop that complemented the indie-folk/blues/jazz influences woven throughout her music. The same scenic setup remained in place for Olivia O'Brien's headlining set later in the evening, with the primary difference being the addition of a drummer and guitarist positioned toward the back of the stage instead of the three sitting in a row up front. Against this shared backdrop, Maya's arrangement kept the focus on her musicianship and songwriting rather than elaborate production.
Moving between the keyboard and harp, Maya showcased different sides of her musicianship throughout her seven-song set. She was joined by Ava McCoy on background vocals and acoustic guitar and Remy switching between lap steel guitar and acoustic guitar, which complemented the stripped-back arrangement. Together, the musicians brought selections from Maya's debut album, Ceremony, to the stage, blending her indie-folk foundations with the soul, pop, and jazz influences that shape her sound.
Between songs, Maya shared the stories and background behind her music, giving the audience more insight into the experiences and ideas behind Ceremony. Those introductions offered context for the songs beyond their melodies, allowing listeners to connect with the songwriting as well as the performance. It was a chance to get to know Maya as an artist, not just as the musician opening the evening.
One standout song on the album is "Georgia the Ceremonialist," which features background vocals from Adrianne Lenker of Big Thief. While Lenker's contribution belongs to the recorded track, the connection is notable for listeners drawn to the contemporary indie-folk scene.
Maya closed her seven-song set with "Tell Me It'll Be Soon," leaving the audience with a final introduction to the world of Ceremony. But her connection with listeners didn't end when she left the stage. She made time to meet fans between sets and returned to the merch table after the show, making herself available to people who wanted to chat or learn more about her music. For an emerging artist, that willingness to connect beyond the performance is a meaningful part of building a community around her work.
As someone who has repeatedly discovered new artists through Olivia O'Brien, I couldn't help but appreciate the full-circle nature of the evening. Maya was another reminder that sometimes the most rewarding part of going to a concert is leaving with a new artist to follow long after the headliner has finished her set.
After Maya Donovan wrapped up her set, it was time for the reason we were all at Irving Plaza: Olivia O’Brien.
Having followed Olivia since 2016, I've watched her career evolve through different eras, from her early SoundCloud days to the success of “i hate u, i love u” and everything that has followed. Over a decade later, she's entering another new chapter with PIXIE, her latest project, a new style, and the reason for this tour. And after watching her introduce me to countless artists over the years, getting to see her bring this new era to the stage for a second time felt especially meaningful.
Walking out on stage with the whole band in pixie wings, Olivia definitely made a mark on the crowd. Throughout the night, Olivia balanced her newer material with the songs that have defined different chapters of her career. PIXIE represents another step in her evolution as an artist, and hearing the songs performed live gave the project a chance to stand on its own while still honoring the music that brought longtime fans to the room in the first place.
One of the highlights was “Icarus,” the lead single from PIXIE, which Olivia shared is her favorite song. There's something special about hearing an artist talk about a song's significance to them, particularly when it's a central part of the project they're currently introducing to the world. For Olivia, “Icarus” isn't simply another release on the setlist; it's a defining piece of this new era.
But while PIXIE may be the focus of the tour, Olivia hasn't forgotten the fans who've been around since the beginning. One of the night's standout moments was a medley of older songs, featuring “RIP,” “NOW,” “Keep It Movin’,” “Inhibition (omw),” and “Tequilawine.” Bringing five tracks together in one performance, the medley revisited an earlier chapter of Olivia's discography while making room for the new era she's introducing with PIXIE. It was a chance for longtime fans to reconnect with her older music and a reminder that her career extends far beyond any single hit or project.
Naturally, no Olivia O’Brien show would feel complete without “hate u love u” her rendition of the Spotify “BILLIONS CLUB” single “i hate u, i love you.” As soon as the song began, hands went up throughout the room. The crowd joined in for the song that introduced so many listeners to Olivia years ago, turning the performance into a moment between her and the audience. Even as she continues to grow beyond the hit that first brought her widespread recognition, the song still has the ability to bring a room full of people together.
Beyond the music, Olivia also made time for some more personal moments with the audience. During a sit-down segment, she shared a story time about the recent headlines involving her and Pete Davidson. With the story circulating online, the moment gave fans an opportunity to hear Olivia speak about the situation in her own words rather than only through the headlines.
There were lighter moments of fan interaction, too. While I didn’t hear the song I wanted to see (Born With A Broken Heart), one fan repeatedly requested “Fuck Feelings,” even after Olivia explained that her band didn't know the song. After saying no several times, she eventually gave in just enough to sing a line for the fan. Although it wasn't a full performance, the exchange was a funny reminder that live shows don't always go exactly according to plan, and that sometimes, persistence gets you at least a little of what you came for.
The connection with fans continued after the show. A few of us waited around afterward in hopes of meeting Olivia, and she came out to say hello and take pictures with everyone. Getting to meet her again and capture a memory from the night was a lovely way to end the experience. After spending the evening singing along to her music and hearing her share stories with the audience, having that opportunity to say hello in person made the night feel even more personal.
Over a decade after I first discovered Olivia O’Brien, I'm still finding new reasons to follow her career. From revisiting the songs that introduced me to her music to experiencing the PIXIE era firsthand, the night at Irving Plaza was another reminder of how much an artist can evolve while continuing to connect with the fans who've supported her along the way.
As someone who covers live music, I always come back to one philosophy: be a fan first, always. It's easy to get caught up in the work of documenting a show, capturing the right moments, or putting an experience into words. But at the heart of it all is the reason I started doing this in the first place: my love for music and the artists who make it. I first saw Olivia at her first Los Angeles show in 2016, and the PIXIE Tour marked my 11th time seeing her live, this time in New York City. After more than a decade of following her career, the experience brought me back to the philosophy I carry - and to never stop making room for new artists like Maya Donovan.
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