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Olvier Wood LIVE at Vinegar Hill Music Theatre in Arundel Maine

Whenever Oliver Wood isn’t touring with The Wood Brothers — the Grammy-nominated roots trio that he co-founded in 2006 — he typically begins his mornings the same way: in Nashville, at home, with a coffee cup in his hand and a notebook in his lap.

“There’s a chair in my living room, right in front of a window,” he says. “Every morning, I go down there to drink my coffee, meditate, and write. It’s like a therapy session for me, because I can write without any specific goal in mind. I can be creative without being self-judgmental.”

Many of the songs from Fat Cat Silhouette, Wood’s second solo record, began taking shape in that chair. Produced by his Wood Brothers’ bandmate Jano Rix, it’s an album of unexpected twists and turns. Longtime fans will recognize the earnest, elastic voice that has always anchored the Wood Brothers’ mix of forward-looking folk and southern country-funk, but Fat Cat Silhouette doesn’t spend much time looking backward. Instead, it abandons convention, breaks a few rules, and positions Oliver Wood as a roots-music innovator who’s every bit as interested in the process as the product.

“I wanted to get outside my box and embrace the uncertainty of what’s out there,” he explains. “I wanted weird guitar tones. The song ‘Yo I Surrender’ has the worst guitar sound I’ve ever heard in my life, and I just love it. I wanted more percussion and less drums. Once we began experimenting and doing whatever we wanted, the pressure melted away and I felt liberated.”

On the album’s opener, “Light and Sweet,” Wood matches an imaginative storyline with a melody that leaps from ground level into the stratosphere. Eight songs later, he brings things to a close with “Fortune Drives the Bus,” which he recorded on an iPhone in his own backyard. While tracking the rest of Fat Cat Silhouette to analog tape, Wood pushed himself to keep things weird. “Making this album was a process of being immediate, making quick decisions, and trusting that the universe and my years of experience would handle the rest,” explains Wood.

Wood’s years of experience have left him with a wide circle of collaborators, and Fat Cat Silhouette features performances from guests like Los Lobos’ Steve Berlin (whose saxophone can be heard on the groove-heavy numbers “Whom I Adore” and “Yo I Surrender”), Ted Pecchio who handles bass duties throughout the collection and Marcus Henderson (who contributes flute and fife to “Whom I Adore”). Co-writers like Sean McConnell, Seth Walker, and Ric Robertson lend their help, too, while Katie Pruitt tackles a verse on the heartbroken soul ballad “Have You No Shame,” which was written by one of Wood’s mentors, the legendary Atlanta musician and songwriter Donnie McCormick. Jano Rix even pulls double-duty as producer and musician, anchoring the album’s mix of mystery and melody with his percussion and keyboards.

Despite the stacked guest list, some of Fat Cat Silhouette‘s best moments find Wood and Rix working together as a duo. On “Little Worries,” Wood sketches a picture of a reflective morning in his armchair — a cat in the window, pancakes in the skillet, anxieties crossing and leaving his mind — over Rix’s inventive pulse. “That song wasn’t easy to finish,” he remembers. “It required experimentation. Jano and I had to give ourselves permission to just be artists, rather than being a part of the music business.” Later, when time constraints prevented them from adding horns to “Star in the Corner,” they chose to sing the horn parts instead. “We innovated by stacking these ridiculous ohhhs and ooohs to create a faux choir sound,” he explains. “It ended up being more original sounding than a horn sound, or at least a little less typical.”

A little less typical, indeed. That might as well be Fat Cat Silhouette’s mission statement. This is an album that finds the art in the unexpected, and Oliver Wood — whose songwriting and vocal chops remain as sharp as ever — at his most adventurous.

Ric Robertson will be starting the night off. Robertson crafts the kind of music that doesn’t beg for your attention — it quietly earns it. One note, one image, one breath at a time. He’s a singer, songwriter, multi-instrumentalist, and visual artist — but mostly, he’s just trying to make sense of the absurd beauty in being alive.

These days, Robertson is mostly out on the road solo, carving out his own odd little orbit, hauling a real upright piano from town to town — a heavy, creaky companion that makes every show a little less predictable and a lot more alive. It’s an old-school, seat-of-the-pants kind of operation: no playback, no safety net, just songs, stories, and a whole-hearted belief that the good stuff doesn’t need a middleman.

Raised in the American South but never easy to pin down, the music floats somewhere between timeless folk wisdom and psychedelic backroom vaudeville. A strange, beautiful blend , he has a gift for turning personal detours into universal truths, and turning heartbreak, hilarity, and hallucination into something you can hum along to.

Robertson has lent his voice, songs, and musical curiosity to projects with artists like Lucius, The Wood Brothers, and Sierra Ferrell, but it’s in his solo work where his vision comes fully alive and his voice shines most true. His latest album, Choices and Chains, is a crooked little odyssey of transformation- following the technicolor psychamericana on his breakout album “Carolina Child”.

Quietly radical, unabashedly grassroots, and fiercely human, you may find Ric Robertson somewhere past the edge of the map — alone on a small stage, an upright piano, a spellbound crowd, and a kind of music that cuts through the noise and reminds you why any of this matters at all. There’s a tenderness here, and a little madness too. But mostly there’s honesty — the kind you don’t come across every day, and the kind that sticks with you long after the music fades out.

Vinegar Hill Music Theatre is an independently-owned event space located at 53 Old Post Road in Arundel, ME. Our charming, historic barn and outdoor garden provide an ideal backdrop for an unforgettable, intimate evening! Learn more here.