The Surge Of Benjamin Shepherd

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I can still remember just how Benjamin Shepherd looked the first time I saw him play.

A guitar strapped to his tall frame, a harmonica holder dangling loose from his shoulders, and his sleeves rolled up past his elbows like he wasn’t concerned if things were about to get messy. He reminded me of Bob Dylan or Paul Westerberg obsessing over the minimalist literature of Raymond Carver or the adventurous cinema of Jim Jarmusch or the immersive art of David Lynch.

Confidence flourished over his entire set as he played through songs like “Franklin-Classon Mile” and “I Can’t Stay Long But I Can’t Stay Gone” with an effortless quality that I hadn’t seen from many of my peers. As songs continued to unfurl from his voice and guitar, I actually found myself growing weary and concerned that Shepherd himself was like a character in his songs, an artist that was simply too good for the community that they resided in and would never be appreciated the way that they truly deserved. In a moment of humility, I’m alright with the idea of admitting I was completely wrong about that last part.


What drew me in so strongly to that first performance was simply how Shepherd sang about life. It may seem like an obvious statement when describing any good musician, but let me assure you: nothing is obvious about Benjamin Shepherd the songwriter. In his songs, he sang about falling in love, succumbing to addiction, watching your neighborhood become destroyed by gentrification, having innocence stripped away from you, authority left unaccounted for, and even suicide.

But he also never seemed to fret over the heavy things. They were points to make, not obsess over, and as I continued to dive into his music, it seemed the most terrifying thing Shepherd could broach in a song would be things actually working out for himself or his lyrical protagonist. There weren’t always lessons learned in these songs, upsides to stumble upon in moments of reflection, but they did provide cherished scrapbook memories of the people and spirits Shepherd immortalizes in his songs. No matter how he chose to detail them, there was no way he’d let the universe turn its back on these fractured anti-heroes any longer.

Going back five years, a cold winter night in January 2014 would see Shepherd begin his relationship with Montrose Recording Studios. The much-acclaimed studio would become the home for the live album that would act as a testament to not only Shepherd’s songwriting, but to his work ethic. Eleven For The Road, released later that summer, was a chronicle of eight years for Shepherd as he wrote and refined the best material that encapsulated that period of his life. From spending time in the anti-folk scenes in New York to riding Greyhound buses cross country to figuring out how Richmond could be something that resembled home to him, he had these songs that represented tucked away road maps of histories that he never wanted to forget.

For one night back then, he performed each of his eleven offerings in single takes to an audience of friends and family. Not much for waxing poetically about the meaning or process behind his songs, he did just what I or any of his peers would expect from him: He let the songs tell the story and he left the desire to attach meaning to it all completely up to the audience to figure out.


It was here where I picked up on Shepherd’s ability to utilize the economy of language in a song. “I want to get across as much as possible with saying as little as possible,” Shepherd stated, and to hear this in action, let’s look at “Silver Dog” from Eleven For The Road. The picking guitar track is a lullaby for any canine companion that follows you across the banks of frost-ridden bodies of water, but it’s also a tale of how we participate in this examination of time and how that relates to animal companions we share the time with. While they remain innocent, we can grow weary of everything around us and we wonder when that sentiment disappeared. Despite the gifts of dead animals, the companion rushes to the sound of your voice and finds comfort in the simple joys of these treasured moments. This is the depth Shepherd brings to each tune he crafts, pulling on imagery of dead raccoons and dirty secrets to both eulogize a pet and romanticize a time period.

Fast forward to the summer of 2017 and I am now meeting up with Shepherd at his house in Byrd Park. As he greets me and invites me in, we begin to realize that this interview might not make any sense. “I don’t really have anything coming out besides maybe a video with Good Day RVA,” he joked. A few months prior, he had released the demo for a song entitled ‘You Got Caught,” a track that quickly details the merciless killings of African-Americans at the hands of uniformed police officers. It’s a song that one of Shepherd’s closest friends and musical collaborators, Charlie Glenn of The Trillions, is drawn to for its quintessential Shepherdian sound.

“Like so many of my favorite writers, he’s able to synthesize a pile of human emotion in a minimum amount of words,” Glenn explained. “The musical elements seal the deal. Then he’ll wander off in a flowing, stream-of-consciousness tome like ‘You Got Caught’ and consider a story in detail, each line as dense and profound as any other he’s written. No real refrain. Every complete thought, of which there are many, are tied together like conversation, as if he just sits down and effortlessly prattles off rhymed monologue when writing. I don’t know, maybe that’s exactly how he writes it. The bastard.”

At the time, Shepherd had been working with the Good Day RVA crew to consider filming a video for this song at an abandoned prison. But as things happen in Richmond, plans changed, and Shepherd experienced an about-face for his own musical approach. Thus enters Kevin Guild into our story, providing a good explanation for how Ben Shepherd somehow ended up with a band. Guild played alongside Shepherd in the punk baseball team, The Richmond Scrappers, and after an invite to see Ben perform, Guild found himself won over by his songwriting charms.


“I knew immediately that I loved what he was doing and from then on I kept bugging him to let me play with him because I really loved his songs,” Guild remembered. “It took a little while, but my persistence paid off and we finally started playing together and we’ve been playing together ever since.”

As the two built a creative rapport, they were able to quickly piece together harmonies and find ways to enhance the music by pushing ideas further. As anyone that knows Ben would say, his perfectionist sensibilities will never change. Before he even brings a song into a room with other players, it’s practically done. And Guild admits that a lot of this hasn’t changed, but there are a few elements that seem to have given Shepherd a bit more of an opportunity as a writer.

“I think the thing that really spurred Ben on was that not only did he have someone new to play with and inject some added life into his songs,” Guild continued, “he had someone with a front row seat to the whole process who was more than anything a fan of what he was doing. And when you have someone like that who you live with and play with on regular basis, it becomes easier to feel the urge to create. I try to push Ben to create as much as possible because I love his songs and I can’t wait to see what he has in store and I get the added bonus of being a participant in all of it.”

One might wonder if Shepherd has adopted any reservations about performing with a band as opposed to the efficiency of working as a singer-songwriter and making every part of the canvas count. Flash back to 2011 and Shepherd is performing alongside several of his best friends in The Veins, a band that was inspired by the spirit of The Replacements. As Shepherd himself put it, “I think we proved to ourselves that we could play shows as black out drunk as possible, or I guess that was up to whoever saw us that night.”

Around this time, he created a tight bond with Chaz Tick from The Veins and began performing with him in The Nervous Ticks and later, Stake. His role in Ticks was predicated on the idea that he could play with a truncated kit, and it also provided a nice distraction from focusing on his own songwriting.

A few years after the Eleven For The Road release, he played a few shows as a trio with Patrick Ball and Adrian Olsen referred to as SLA. A lot of these songs were ones that captured the mood and matured interests of Shepherd, and it is here where he took his songs about recluses and anti-heroes to new lengths. From this batch, “Molly, The Minors and Me” is a personal favorite of mine. It’s the story of a minor league baseball player who runs his mouth about the big leagues and making it someday, but never seems to notice that he’s the one thing at the bars who hasn’t changed in the slightest. This story seems to have fashioned how Shepherd perceives success versus having art be a part of your life in order to feel sane or like a complete person.

“I was reading up on these minor league baseball players and I became fascinated with the ones that never really made it,” Shepherd described. “A scene played out for me of these guys just surrounding their local dive and acting as if they had still somehow succeeded when all signs might point to them doing the total opposite. The idea of making it isn’t really something I put much thought into. I don’t write unless I feel a reason to. Forcing yourself to write something isn’t fun to me. I find that even just sitting around and playing guitar for two hours alone is a lot more interesting to me than pushing around ideas that might never go anywhere.”


As Shepherd began readying a number of new songs and working on them with Guild, Charlie Glenn entered the story once more, acting as a guardian angel again by offering the chance to go back to Montrose to work on an album comprised of these tunes, this time backed by an entire band. While Shepherd had been sharpening his sound and broadening his skillset, Glenn had been working steadily with his main outfit The Trillions while also performing alongside bands like Thao And The Get Down Stay Down and The Head and The Heart, with the latter band’s drummer, Tyler Williams, also offering his support and advice for yet another bright and talented Richmond musician. This time around, the idea was to go in with Shepherd’s songs and just run full speed ahead. Try any idea with engineer and mastermind Adrian Olsen, pick the best take, and just go from there. The idea seemed tenuous and crazy, but it makes perfect sense for the type of adventure and journey that typically inhabits a Ben Shepherd song.

One weekend recording at Montrose and they had nine songs. Mostly new ones with a few older offerings thrown into the mix. Some songs recorded in the studio. Some songs recorded with just Ben and a guitar on a backyard porch and a microphone dangling to capture all of it. Reaching both to his past sound and future aspiration, it looked to bolster the charm that separated Eleven For The Road from other live-to-track album with a robust cadence that only a full band could provide.

The first single off this yet to be titled album was “Friday Fantasy,” released this past January. It’s a song that feels like the earned epilogue for any of Shepherd’s protagonists, as you fall into a night spent falling in love and watching the world around you become something that excites you again. It’s a bit Tom Petty at times and it’s all the better for it. As the grooves and kinks work their way out through the song, Shepherd enters the scene with an offering and an affirmation that shows he’s ready to grow into a person that would humor the idea of romance and a future assembled with another.

This is one of the many general vibes captured in the new album, a rejuvenation and a course ahead that feels like concern for failure hasn’t dissipated. That failure isn’t an anchor that would prevent the protagonists from trying to get to where they were always supposed to be going all along. It even seems like the journey Shepherd has been on has led him to a point where he generally seems more optimistic for the future ahead.

The next single from this record is “’96 Corolla,” a track that many might be familiar with due to a previous version closing out the Eleven For The Road record. Written about the despair of an artist that was left with only the will to escape, it might be a perfect antidote to the former self of Shepherd and how his perception of that lingers subtly in his new material. He has let go of his past in order to allow himself to enjoy the future ahead, and “’96 Corolla” provides a perfect chapter closing summation in its somber tone.


Through it all, Shepherd is a romantic at heart who taps into the truth of this personality on every song he has ever written. Each tune contains a sense of hope, even at the bleakest moments, providing a balance beam of life and our choices that helps guide his pen as he considers each new sonic venture.

On this upcoming collection, Shepherd allows himself to be a new version of the songwriter we have all come to know and love, the most fully realized version that can conquer the challenges that the world sets in front of him. This is the Benjamin Shepherd we were all waiting for, but his next chapter will surely be something we could never have expected.

All the same, we will all be eagerly anticipating turning the page with him and experiencing what comes next.

”’96 Corolla” by Benjamin Shepherd is available to stream and purchase at, and make sure to catch his album release show on Friday, May 10th at Richmond Music Hall alongside Piranha Rama and The Trillions.

All photos courtesy of Sarah Walor, except the live photo which is courtesy of Joey Wharton.


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