An evening riding the crest with Anna Barnett.
I’m sitting across from the lead singer of the New York City indie pop band Sweetboy at a back-corner table in a dimly lit but bustling Greenwich Village tavern on the Bowery. Less than four hours from taking the stage a few blocks down, Anna Barnett looks gorgeous in her glam-decadence black dress, swept platinum hair, and glowing earrings that frame her tender smile. None of it, especially her guarded politeness, can mask the pensive soul before me. I idly wonder how she might describe her career with the band after seven years. Without hesitating, she intones, “I’m standing on a cliff.” We are off and running.
“This evening, in particular, could be the beginning of a very sad, somber period with my partner and co-founder of this band leaving suddenly,” Barnett begins. “And now everything is mine to either make or break – even tonight’s show. It all depends on what I do now, and I want to jump… as long as I’ve got the energy and the confidence to say, ‘Yes, we’re all in this, we want to keep going.’ But, I don’t know. I still feel in danger because I could just as easily say, ‘This is going to be ton of work, I’ve had fun, so let’s just have a normal, easy life.'”
At 33 years old, Barnett is understandably considering the impact of her creative partner, Jonathan Flores, leaving after years of fruitful output. It is a painful reminder that time is a bitch, and the trajectory of a musical outfit can be a mercurial and an oft-times frustrating ride chasing elusive success, and more pressingly, creative progression. It may also be a reminder that he’s the smart one choosing this “normal, easy life.”
To look at Jonathan Flores it makes perfect sense he’s chosen the more pragmatic route. A bespectacled, mustachioed professorial type, he appears closer to a computer programmer than rock keyboardist, but that is a lazy interpretation. He has been the backbone of Sweetboy’s early sound, his quiet cool reflected in most if not all their music videos with Barnett. The two have worked tirelessly to make unconventional pop songs that perk the ears with spastic rhythm changes and quizzical lyrics realized in the studio or recreated live with great care by the band. Sweetboy’s music evokes the early days of new wave with an electronica slant, pushing the boundaries of how a pop band can also experiment freely.
Until now, it was all Jon and Anna. After the show this evening, that will change. So, I must ask, “What does that mean?”
After looking up for a moment, Anna leans forward. “Jon’s sometimes more conservative than I am, even though I consider myself kind of conservative in some ways, and so we were both less willing to take risks,” she says. “Our styles have become a little bit different, too. I thought they were more similar than they are, but I guess I’m the one who changed. We weren’t always on the same page with things. Not personally – we always got along. I love him.”
I let the last statement hang in the air, and leaning back in her chair, Anna continues as if I’m not sitting there. “Jon and I had a shared vision, and we went through this big branding exercise a year-and-a-half ago to come up with our keywords and match our colors and our style to all that,” she says. “I think it worked well to blend us, but, like I say, I’ve changed… ad the band’s changed since we brought on new members. Connor (O’Sullivan, guitarist) and Nick (Oddo, bassist) have more of a Nirvana background, so they’ve already pushed us a little harder. Connor and Nick have said to me many times, ‘You’re it; we’ll follow you anywhere, everything you do, we want to be behind it,’ which is very comforting and inspiring, so I just have to trust myself to forge ahead.”
I assure Anna that Sweetboy has already illustrated a stark evolution of their oeuvre since I introduced them on the stage at the 2023 Underwater Sunshine Fest, reflected in last year’s diverse and engaging, A Day in the Park, and their recent bevy of singles: The pulsing “Save Me,” in which Barnett sings about lifting her spiritual fulcrum over another kind of cliff, “Heart, beat” a tumbling piano workout that rides a honied melody to best contemplate the measure of grief, and the post-new-wave bop of “Holy Roll” that she describes as “You think everything can be tied up in a neat bow and you can be rescued, but life’s not like that. I wanted to be woken up – hearing the first whisper, ‘I don’t like this’ that roused me from a fundamental feeling that I had over my whole life of this perfect Christian girl.'”
From that awakening and over the course of the band’s musical growth, Barnett has settled neatly into her idiom as a performer. She is a dynamic presence in the spotlight who can provoke with the mere tilt of her head or raise of an eyebrow, or suddenly become loosed into a frantic flailing spin. Her voice, a flexing lilt, clinches her lyrics with unblinking intensity. She exudes a smoldering energy, even now when chatting over candlelight. This is summoned, it seems, from years of spiritual and personal liberation from that “perfect Christian girl.”
“I was raised Evangelical, very fundamentalist, but also a little bit counterculture and rebellious,” Barnett recalls. “My parents kept us out of school because they wanted to protect us from secular thinking, but they were also against the system telling us what we needed to do. So, we basically taught ourselves, and that made me very independent, and, ironically, it was that kind of rebellious streak that gave me permission to eventually question Evangelical thinking. Once I went to college and started learning more worldviews, met cool people that weren’t exactly like me – or even Christian – and people I respected who were more liberal minded that my belief system became far less black and white. It was all nuanced. It didn’t turn me agnostic or atheist because I’m still interested in reading about spirituality in general and other more progressive Christians takes on different things. There’s still a large part of my heart that’s Christian, but I felt free.”
These tenants will be challenged after the show tonight. With Flores on the cusp of leaving, it marks a prologue to a new chapter in Sweetboy, which Barnett defines (again) as a freer, more focused sprint to where the band must go to grow, channeling that sense of epiphany to her professional goals. “I want to be one of those bands that write songs that are so universal they can reach a huge crowd in this cathartic and optimistic or emotional way without being super sentimental,” she says. “And not to say we’re as good, but in the way that the Beatles or Queen or Fleetwood Mac does. Their songs are amazing for the welling that you get in this energy. I want to be that band in both the songs and on stage. I think we’re getting a little bit more acoustic, finally getting away from all these synth pads and digital sounds, which I love, too, but I think we need to enter a brighter phase, because music also gives you energy in your real life.”
For Barnett, this means Sweetboy must reflect its times. “We need to be more political, too,” she states emphatically. “There hasn’t been, in my opinion, a great band recently that tackles politics and social issues outside of rap or punk music. Punk music is allowed to be political, but what about pop rock? Why can’t that be political to get us doing something? I don’t know. I just get a feeling that there’s something important that I can add to the music scene if I have the energy to do it and if I trust myself to figure it out.”
Finding herself at a crossroads suits Barnett. At some points during our discussion, she teeters on utter despair before rallying with a sense of enviable purpose, which has been a lyrical theme-set from her time writing with Jon, this magnetic push and pull of positive clashing against the negative – manifesting the “perfect Christian girl” and the “rebellious spirit.” Seeing both sides of the constant conflict of life, love, family, partnership, and band is a needed perspective moving forward. When we leave to walk to the Bowery Electric, the place that will house the final chapter in the first book of Sweetboy, she wants to talk more about me, about the city, about the weather than the task facing her, quietly preparing to sing those songs of the dark and light and figure out where they’ll lead.
“I want to be more…. aggressive in leading this band,” she finally says before we enter the club. “I’m just really blessed to be in this moment.”
Later, I catch Anna pacing, struggling to keep her attention on one of the other acts roaming the stage she is about to step onto for the last time with Jon, and bid ado to the first phase of Sweetboy. Occasionally, she’s approached by a friend or fan and does her best to smile and interact, but she is clearly somewhere else. Days later, she admits, “I felt closed in and nervous before we went on, and I didn’t really talk to people. I felt the same from Darby (Brandon, drummer) and Nick. Jon, too, also felt closed off.”
Sitting alone by the merch table, Flores takes it all in and is visibly moved by the sudden presence of his former guitarist, Chester Drago. “We haven’t seen Chester since he left two years ago,” Barnett, also shocked to see him, tells me later. “We didn’t know he was coming. He just tapped on my shoulder, and it made me feel such joy and sadness to see him, but mostly relief. He left to have a baby and he’s just been busy and hasn’t come to any of the shows.”
Drago has come to wish his old mates well and will eventually join them to play one of his own contributions, “Bad News” in a nostalgic trip that leaves Barnett nearly in tears. I overhear an emotional Flores tell him before the show, “The whole thing is bittersweet.”
“I saw John tear up and it was such a beautiful moment,” Anne later tells me. “And that’s when I first started getting ready to actually go on stage and knowing this is going to be okay.”
It is a strange evening for everyone, as O’Sullivan, Drago’s replacement, later watches the impromptu reunion excitedly from the audience, a proud smile creasing his face. It is a moment Barnett will cherish, confirmation that the musical family she and Jon built is legion. When I press Flores on his decision to quit before he heads to the stage, he straightens his stance and tells the interloping journalist that “Oh, I’ll still be writing songs with the band.” The roots of Sweetboy indeed run deep.
“I’m all in. Completely,” says an exited O’Sullivan, gearing up for the show. “I have put my all into this band and I believe in it.”
Before Sweetboy takes the stage, there is a buzz in the room. Many fans have traveled far and wide to see this show, fully aware of its importance as a turning point in the band’s story. It is a goodbye tribute to Jon but also a launch into what they hope will be an exciting future.
The musicians respond immediately, coming out swinging with the 2022 track, “Island,” a song that tussles with the inner turmoil of building autonomy without succumbing to social isolation. Swaying purposely as she sings its opening verses, Anna appears to be emerging anew. From my vantage point in the upper bar area, I catch her eyes, as if she is telling me, “This is it,” the Rubicon she must cross is being traversed right now – not tomorrow or next week. Expressing the aggressive future she’s envisioned one chord and beat and note at a time, she sings, “They say no man is an island, but I am… no… man!” She stomps her feet with each syllable, a physical exclamation not lost on the rest of Sweetboy.
“We came out there and broke through immediately,” she recalls later. “The beginning of every show is always that question for me if I’m going to come out and be awkward, maybe it’ll take me like three songs to break through. Not this time.”
Taking her lead, the band dives headlong into the breech. At its stirring coda, the eruption behind her is stark. O’Sullivan’s long, red locks flow wildly as he hammers down on the strings, Odo’s head bangs to Brandon’s relentless backbeat laying the groundwork to the drummer’s feverish pounding which underscores the swirling humanity before her. As always, Jon plays his part; half smirk, half dour, driving the proceedings without effect. After the opening number, Barnett is short of breath. “Wow, I have to calm down,” she tells the cheering audience, “if I’m getting through this.”
Smiling a few days after over a Zoom call, Anna is pleased that the band coalesced so effortlessly that night, sharing a brain and a soul. “I just let go and we just performed. I found myself moving… a lot, and about halfway through the song I turned around and realized everybody else was moving a ton! They were in synch with me, and we were wild and uninhibited and free. It hit me – it really is up to me. It had never been as clearer to me my effect on them and their effect on me! We were pulsing, and I remember thinking just then, ‘We can do this, and this is what my life should be.’”
The rest of the show was a stroll through Sweetboy’s rich musical history, touchstones of their catalog unfurling as if a waning yellow brick road. Barnett catches the eye of her partner, and he smiles. Anna and Jon have made some great music together, first as a duo and then believing in its power to form this band and lead its twists and turns. Now it is up to Anna Barnett and those who see the great unknown as a roadmap and not the abyss; the cliff becoming a clear slalom to something richer.
The band closes with “A Day in the Park” in another exhibition of pure passion. Each exiting the stage to leave Jon Flores alone playing his keyboard as he did to start all this. He never looks up, slowly playing “When the Party’s is Over.” Fighting back the tears, he closes the show to a dense round of applause. The room is drained. Sweetboy slayed it. The past honored, wrapped neatly, and nestled away. The future beckons.
“Did you cry?” I ask Anna days later.
“I did not cry until right before John was leaving,” she remembers with a smile. “It was just so much of a welling and then he was about to leave… and I gave him one last hug and then I started sobbing, ugly crying.” She sighs, “It was embarrassing, but that’s just how my emotions come out.”
Emotions, of which she will now be free to pursue in whatever becomes of Sweetboy in song, stage, and story.
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