After Hitting the Road, Raphael Shapiro Returns to The Talkhouse To Make Music Where It All Began

Longtime residents of the East End may remember the many creative gifts of Raphael Odell Shapiro. A wunderkind of the local stage, as it were, Shapiro was a young singer, actor and dancer who, in his middle and high school years, wowed audiences with his prodigious talents in plays and musicals.

That was close to two decades ago, and in the years since he dominated the youth theater scene on the East End. Shapiro, a Sag Harbor native (who now goes by the moniker R.O. Shapiro), earned a degree from Yale University and set out to hone his craft throughout the U.S.

But Shapiro is not pursuing acting as an adult. Now 34, he has instead settled nicely into music as his chosen career path and this Friday, he returns to his hometown to share his talents as a singer, songwriter and purveyor of original Americana music in a gig at The Stephen Talkhouse in Amagansett.

When reached by phone for a recent interview, Shapiro was in Nashville preparing for this upcoming tour. He explained how his transition from acting to music making came about.

“I picked up the guitar in my senior year of high school at Ross,” he said. “I joke about my classmates and the school librarian near my desk area hearing me play ‘Blackbird’ a thousand times that year.”

Shapiro added that he was also an admitted fan of Bob Dylan and Neil Young in his youth, as well as the whole 1970s music scene. During college, he remained involved in theater, but he also branched out by doing a lot of singing, which is a long-standing tradition at Yale where students have a wide choice of a Capella groups and bands to join. That’s when Shapiro discovered Tangled Up In Blue, a chorus group at Yale that focuses primarily on American folk songs.

“I just fell in love and learned more about the genre and catalog and traditional tunes as well,” he said. “The melodies, stories and the whole culture around it. It wasn’t just centered around the concerts, but we would hang out afterward sharing original songs or sad covers you’d never heard before. I was hanging on every word and enjoying friends, playing these songs and finding favorite musicians. We would just be singing beautiful, simple harmonies of folk music.

“It is still something that keeps me coming back.”

The camaraderie, the melodies and the messaging of folk and roots music struck a chord with Shapiro, so to speak. Though he moved to New York City for a time after college to pursue acting, he soon came to understand that it wasn’t a good fit for him and so he shifted gears.

“I realized I had a bit of a traveling bug and I wanted to get a little further afield,” Shapiro said. “I had lived on Long Island, Connecticut and was now living in New York City. I wanted to expand my perspectives. It’s not impossible to do that in theater, but the ease of traveling, the autonomy of throwing a guitar in the car and popping into a bar, a library, or even an old folks home appealed to me.”

The call of the road led Shapiro to California, and then Austin, Texas, where he settled down for four years. There, the city’s burgeoning live music scene gave Shapiro the platform and opportunities he needed to hone his talents as a musician, singer and songwriter and it seems to have paid off. In 2022, Shapiro was a winner of the Kerrville Folk Festival New Folk songwriting contest in Texas, and in 2024, he was a finalist in the North Carolina-based NewSong Competition. He has toured with musicians May Erlewine, Jeffrey Martin and Taylor Ashton, and in conjunction with his Talkhouse gig this week, on Friday will release “Worthy EP,” a four-song EP that he recorded in part with producer/instrumentalist Phil Cook (Bon Iver, Hiss Golden Messenger.)

Odell, who is now 34 and lives in California (his fiancée, Lauren Tronick, is currently a medical resident at Stanford University), will perform at The Talkhouse alongside fellow musician, singer and songwriter Rachael Davis, who is 10 years his senior and lives with her family in Nashville. Like Shapiro, she has spent a lot of time performing on the road.

“Rachael and I met at Blissfest in Michigan a year and a half ago or so,” Shapiro explained. “As the story goes, her dad was also at the festival. He heard me play my set and went and got my CD and played it for her the week after the festival. She loved it and a week later, she sent me a clip of her recording of one of my songs.

“Rachael invited me to come on her tour this past spring. This is the second time we’re doing a run together,” he added. “For this kind of tour, we will be onstage together, swapping songs, going back and forth and supporting each other on different songs.”

Touring with Davis hits a lot of high notes for Shapiro. It allows him to collaborate to some extent while also maintaining his autonomy as a musician.

“This has been a really fun way to mix it up and be able to sing harmonies while still being a solo artist,” he continued. “It’s not a full band commitment, but we share each other’s networks and audiences. Rachael is an incredible vocalist and musician and it’s such a fun time hanging out on stage.

“I’ll be playing guitar, but I’ve also been bringing tap dance back to the shows, tapping along with the singing,” he said.

This current tour began in the Midwest with stops in Chicago, Indiana and Michigan (where Davis is from). Along the way, it will hit spots that figured prominently in Shapiro’s formative years.

“Then we’re making our way east across the Great Lakes region, then into western Massachusetts, upstate New York and the initial show that got us on this tour — Winter Hoot at the Ashokan Center in the Hudson Valley.”

The pair will then head to Boston and Cambridge, where they will play Club Passim in Harvard Square, followed by a gig in New Haven, where Shapiro attended college.

“Then we’ll take the ferry across to the East End, and after the Talkhouse, our last show will be in the city at Bitter End.”

When asked to expound on where his songwriting inspiration comes from, Shapiro notes it is an accumulated life experience.

“My writing has always been very personal. They say write what you know, it comes from my core and whatever major themes are playing out in my head, heart and life at the time,” he explained. “There’s always with an eye on the universal and trusting that we’re all more similar than different. It’s keeping an eye on the rest of the world too, trying to bring in bigger social themes. Then there’s place. It’s something that’s really effective in songwriting — being specific about setting and the more places I go and people I meet, the more I have to write about.”

These days, Shapiro splits his time between the Bay area in California, where Tronick is doing her residency, and Mendocino, a coastal community three hours north that appeals to his small town sense of community.

“I’m helping to book shows at a venue in the small town of Caspar,” he said. “It’s a cool challenge to book things.”

True to the post-collegiate vision for his life, it seems Shapiro has found much of what he was seeking when he set out on the journey, and has seen a good deal of the U.S. along the way. Which raises the question, as a born and bred East Coast boy, what has Shapiro come to learn about the rest of this country through his time as a traveling musician?

“People say they’re surprised I’m from New York. I also think people don’t understand the East End,” Shapiro said. “I feel I grew up in the country, even though it’s a funny kind of country. The slower and quieter pace appeals to me and I’ve been able to find a lot of communities on the West Coast that remind me of there. Mendocino, Southeast Alaska, British Columbia — maybe these places have a tourist economy, but there are remnants of blue collar industries that started there.

“I really think the through line is that all these places have beautiful, different cultures and their own weird snacks and slang and sense of style. But at the end of the day it ain’t all that different — and I relish that.

“There’s cool stuff and cool people everywhere,” he added. “It was so interesting telling people from the coasts that I lived in Austin. They’d say, ‘That’s the only place I’d live in in Texas.’ Far be it me to judge people by the government or the people in it, but Texas is amazing — you have Houston, San Antonio and El Paso, not to mention funky small towns.

“There are places like that everywhere. Something I love about this career is experiencing these places and connecting with people. Sharing songs in small places, being vulnerable and personal, leads to people doing the same with me.

“I’m really excited to come back to The Talkhouse,” he added. “It’s such a reputed and historic venue in the area. So many amazing people have played on that stage, it always feels exciting to be on it.”

R.O. Shapiro and Rachael Davis perform at The Stephen Talkhouse on Friday, February 7, at 8 p.m. Tickets are $22 to $28 at stephentalkhouse.com. Stephen Talkhouse is at 161 Main Street in Amagansett. The gig is also a release party for Shapiro’s four-song “Worthy EP.”