Take the Long Way Home: August Gladstone Shares New Music in Sag Harbor

After earning his undergraduate degree from Boston’s Emerson College in 2022, like many young creative souls, August Gladstone decided to head west to Los Angeles to pursue a career in the entertainment field.

Gladstone, a Springs native and East Hampton High School graduate, had majored in screenwriting with a minor in comedy and he had been part of a sketch group at Emerson for all of his four years there. In Los Angeles, a bastion for television and comedy writers, he landed a great job in the business where he got to see firsthand how it all worked.

But instead of inspiring him, what he witnessed in the job gave him the impetus to change his career trajectory entirely.

“I worked in talent management and was seeing the business side of the arts,” Gladstone explained. “Through no fault of the company — they were wonderful — the TV industry and film industry are in a very rough situation right now.”

It’s true. As mega players like Netlix, Skydance and Paramount — backed by some of the richest men in the world — go to war in an all-out effort to control as much of the entertainment universe as they can, recent college graduates like Gladstone are left wondering what sort of future they might hope to have in the field.

“There’s been a massive contraction of the industry, which has been happening since my graduating class and I got into it,” he said. “Traditional pathways have become quite occluded. It’s a troubling feeling.”

In other words, “Our generation is f---ed,” he added poignantly. “The industry will self-correct. From my experience, the entertainment industry, more so than any other, is on a pendulum. It operates in booms and busts, depending on the technology and what people are using for entertainment.

“Entertainment will never go away and will always have a place,” he added. “But at the present moment, it’s in a bit of a free fall and no one knows what the future holds.”

For artists and influencers of any stripe, platform algorithms and the insatiable appetite for constantly new content is what drives metrics. Whether it’s AI or a real-life viral video, that traffic equals revenue — the ultimate measure of “success” in this media-obsessed culture.

But for Gladstone, chasing that sort of success not only seems unsustainable, it also feels hollow, contrived and soul-killing — a model based on someone else’s definition of a dream. The real winners are those with a financial stake in the platforms that can’t get enough of whatever it is driving engagement and therefore, profits.

Meanwhile, most content creators — and their fans — find themselves increasingly isolated in their silos, documenting for countless eyes on endless platforms a life they may not actually be living.

Enough, decided Gladstone, who is now pursuing music, an art form that evokes immediacy and real-world connection through a more traditional way of communicating. His new creative path as a singer/songwriter is as old-school and authentically in-person as it gets — writing original music and performing it on his guitar in front of live audiences.

Imagine that.

“I’m still a sketch and comedy performer. I’m also invested in the world of filmmaking and entertainment,” he said. “I’m just taking a different approach.”

That approach will bring him back to his home turf this Sunday, December 21, where he will perform a 6 p.m. concert at the Masonic Temple, located upstairs from the Sag Harbor Historical & Whaling Museum. Joining him on stage will be Springs siblings Liz Vespe (a former Express News Group reporter) on fiddle and her brother, Paul Vespe, on lead guitar.

Gladstone will have a lot of new music to share with the hometown crowd, as he has been gaining recognition on the indie music circuit in Los Angeles as of late. His debut EP, “Commodore,” was released in July 2025. Currently, Gladstone is working in the studio with producer Mark Hart (who also worked with Supertramp and Crowded House) on a full-length album that is set for release early in the new year. His Sag Harbor performance will offer audiences a preview of material that will be on the forthcoming album.

“I strive to make work that is utterly human, imperfect,” Gladstone said when asked to share his musical vision. “On the digital side, everyone is trying to present a polished version of themselves. I push myself to be explicitly vulnerable and write about things I’m scared about while also having a sense of humor.

And what is he scared about?

“I’m scared of a dying world. Feeling powerless. Being trapped in a place where we were never supposed,” he said. “I want freedom, love, a vibrancy of self and spirit. It’s terrifying where we are headed. I don’t wanna be all doom and gloom and things are darkest before the dawn. But a lot of people right now are scared of fascism and the government.

“This is a straight up evil Star Wars empire. That’s where the comedy comes in,” he added, noting that one thing he isn’t afraid of is creating topical, politically engaged work from time to time and immediately sharing online. “The work I record is more personal, existential and surrealist in its bent. It’s focused through the folk tradition and more abstract. The lyrical absurdity balanced with honest imperfection of it all. It’s as representative of my existence as possible.”

Gladstone explained that his career as a singer/songwriter was born of out of poetry and the fact that in his job at the entertainment office, he was seeing just how slowly everything moves and how unlikely it is that projects will ever come to fruition.

“You can spend years on a script and have it snapped away in a second. That’s difficult to stomach as a creative and an artist,” he said. “I wanted to do something more immediate where I didn’t have to go through 10 years of cutting my teeth. So, I started writing poetry and sharing it live.

“It was wonderful and life-defining. I discovered a new side of me — I can write it today and share it tonight and have a connection with people,” he said. “The music grew out of that because no one reads poetry. My music is tricking people into reading poetry.”

Just as old-school turntables came back in style the minute all the Baby Boomers had gotten rid of their vinyl collections, so too, it would appear that for creative souls like Gladstone, the next great countercultural movement is performing live in intimate settings.

“It’s a complete rebuttal to AI and living in a fractured fantasy world where every piece of information is subsumed by the next one,” Gladstone said. “People are really done with this technology. My entire issue with this cult at large is that it’s putting us into a hell of our own design.”

Still, Gladstone readily admits that, as someone who wants to be a successful artist, this dichotomy is hard for him to reconcile at times.

“Of course I want success. But I don’t want to find it by compromising the integrity of my work, especially in the digital age when music and art have become ‘How fast can I drive this,’” he said. “The algorithm aspect encourages artists to put more and more of themselves out there with no promise of return.

“Social media is destroying every creative outlet we have.”

For that reason, Gladstone limits his contributions on TikTok and Instagram to short snippets designed to market his talents, rather than being a creative outlet for them all.

“It feels necessary,” he said. “I have to play the game. But I try to post work that is not designed to feed the algorithm.”

So, these days, if you really want to get to know Gladstone as a singer/songwriter, you’d be better served by seeking him out in person. When he’s in L.A., that means heading to rock clubs like The Viper Room on the Sunset Strip or the famed Troubadour in West Hollywood.

“That’s an awesome venue,” he said.

Finding inspiration in the folk revival of the 1960s and 1970s and artists like Bob Dylan, Leonard Cohen and Joni Mitchell (all of whom played the Troubadour at some point in their career) and singer-songwriter Townes Van Zandt, a self-described “Texas Troubadour,” Gladstone describes his sound as “honest, folksy and not offbeat” with lyrics that explore “surrealism, intimacy, humor and political activism.”

His new home turf also provides strong inspiration for Gladstone, who is taken with the concept of the Wild West and recently took a road trip where he explored the wide-open spaces of Idaho, writing a few songs along the way.

“The West is intrinsically linked to seeking your dreams and finding your fortune,” he said. “It’s the grandiosity and beauty of the land and how oppressively beautiful the space is out here. Even today, it feels untamed. I think that’s a great beacon for artists everywhere. There’s a history of going west to seek your fortune.

“It was a time of rugged honesty and people who didn’t fit in. That cowboy image and the outsider nature resonate with me,” he said. “I’ve found a brand-new audience on the West Coast. The world is fresh again. We do ourselves a disservice if we remain too comfortable. We need to explore.”

So, now that he’s been living on the West Coast for three years, does Gladstone feel that he is finding the kind of success he had hoped for when his journey began?

“The goal posts always shift,” he said. “I’ve only been making music for about two years. Considering that, it’s going really well. I’m proud of where I am, based on where I was. I’m proud of the projects and my work. What’s important to me is live performance — being in the room with people. I’ve had a show every week for the last six months, so in terms of growing my musical career here, it’s successful. The only thing you can focus on as an artist is what you can do.”

Singer-songwriter August Gladstone performs at the Masonic Music Series on Sunday, December 21, at 6 p.m. Tickets are $20 at the door or in advance at masonicmusicseries.com. The Masonic Temple is located above the Sag Harbor Whaling & Historical Museum at 200 Main Street in Sag Harbor.