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Autograph Adventures – Ray LaMontagne, Life is good Festival

September 24-25, 2011
Canton, Massachusetts

Twelve miles south of Boston, Prowse Farm sits at the base of Great Blue Hill which overlooks the 6,000 acre Blue Hills Reservation. Though technically suburbia, it feels like the middle of nowhere.

Ray LaMontagne autographed program

Ray LaMontagne autographed this program for Matt

In the middle of the farm, the Life is good Festival is spreading good vibes through a potent lineup of national music acts and kid-friendly activities. Thousands flock to the event each year to take in the sights and sounds during one especially optimistic September weekend.

In the middle of the artist hospitality area, there is a white tent beneath which sits a simple leather couch and an easy chair. The coffee tables are hay bales—farm chic.

In the middle of the tent stands Ray LaMontagne, looking like a Gangs of New York extra. And after meeting this talented man of few words, you get the impression he’d be content blending into the background.

I joined about twenty others for a meet and greet in this unique setting and, while photos weren’t allowed, the singer spent a few moments with each fan and signed autographs.

When it was my turn I asked Ray about fame—a seemingly unwanted byproduct of doing what he loves very, very well and a phenomenon he consciously tries to mitigate.

“I do what feels comfortable,” he says. “I have friends that say, ‘Ray, you need to get your face out there more.’”

He looks away, shakes his head slightly. “It’s real easy to date supermodels when you play the guitar. That’s the easy way to get yourself out there. It’s real easy to date actresses. But that’s the easy way to do it. I have a different approach.”

LaMontagne’s aversion to celebrity is an interesting dilemma as commercial success and anonymity are mutually exclusive. His approach, it seems, is to limit his exposure to environments where he is in control and where there is a barrier (sonically and otherwise) between him and others. But even then he shares the spotlight. During the evening’s set, he and four other musicians appear side by side with LaMontagne positioned on a far end.

4 More Successes at the Life is good Festival

The Music Choice tent afforded fans the opportunity to get up close with several artists. Following an interview and interactive audience Q&A, all the musicians I observed hung around to meet fans.

Tristan Prettyman (autographed program) – Once a surfer and model (and Jason Mraz fiancée), Prettyman is a talented singer-songwriter from San Diego. Ahead of me in line to meet Tristan after her interview were three young children who were unsurprisingly bashful about the encounter. After taking a photo together, Prettyman suggested they take “a weird-face picture” in attempt to bring the kids out of their shells. It worked, and they posed again sporting their most bizarre and humorous expressions.

Naturally, I asked Tristan if she’d like to take a weird-face picture with me. She agreed:

Matt Raymond and Tristan Prettyman

Matt Raymond and Tristan Prettyman having some fun at the Life is good Festival

Ingrid Michaelson (autographed program) – You’ve probably heard Ingrid’s songs without knowing it as her music has been used several times in advertisements and television shows, including Grey’s Anatomy and One Tree Hill. Mrs. Raymond and I met Miss Michaelson during a meet and greet.

Raphael Saadiq (autographed program) – I met the R&B singer/producer (and former member of Tony! Toni! Tone!) following his Music Choice interview. Great with fans, a musical genius and the smartest dresser at the fest.

Zee Avi (autographed program) – I hadn’t heard of this Malaysian-born singer before the festival but quickly became a fan after hearing her beautiful music. She also makes me look like a giant.

About the author: is the founder of Autograph University. He lives in the Boston area with his wife and two sons. Connect with him on Twitter at @mattraymond.

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