The first time The Tom Fun Orchestra performed for an audience, more than a few of the musicians in the band were playing songs they’d barely heard once, if at all. It was 2005 and the East Coast Music Awards were being held in Sydney, Nova Scotia. Though he’d only been writing and performing his own music for a few months while travelling in Scotland, singer-songwriter Ian MacDougall decided he was ready to perform for his hometown, and figured the musical event was as good an opportunity as any for a show. Two days after his return to Cape Breton, MacDougall was onstage with nine friends, performing his songs for a crowd.

“We’re a bunch of friends doing something absolutely ridiculous, and who now get to travel to weird places together.” – Ian MacDougall

“I imagine it was terrible,” laughs MacDougall in his characteristically self-deprecating style. “I think that’s why I wanted to have such a big band. I figured if there were enough of us, we couldn’t be that bad!” But early audiences responded well to the band’s eclectic energy, comparing them to everything from Broken Social Scene to the Pogues. “We were fueled by the feedback,” MacDougall recalls. “We realized we enjoyed it and wanted to take it more seriously.”

Two full-length albums and a handful of awards later, The Tom Fun Orchestra is still going strong. While the band currently tours with seven people (ranging in age from 24 to 42), more than 30 have been included on the roster over the years. “It’s nice because there is such an abundance of talent around here,” says MacDougall, who sings, plays guitar, and writes the songs. Though he didn’t grow up playing music, MacDougall, who has a “fondness for words in a big way”, was first drawn to songwriting because of the space it allowed him to play with language.

“I figured if there were enough of us, we couldn’t be that bad!” – Ian MacDougall

With a new album in the works, the band’s sound continues to evolve (recent incarnations have made room for more guitars and fewer fiddles). MacDougall says he’s constantly amazed and thankful that their music has taken them as far as it has – including on tours through Australia and the U.K. “I think what’s really special about this whole thing,” says MacDougall, “is that it’s a bunch of friends doing something absolutely ridiculous, and who now get to travel to weird places together.”

Track Record
• Tom Fun is a nickname that MacDougall says he “got stuck with a long time ago”. The band’s early incarnations were all variations on the theme, but they settled on The Tom Fun Orchestra when it came time to record their first album.
• While he says it is never intentional, MacDougall admits that Cape Breton often creeps in as a theme in his writing. “It’s where we grew up and where we have spent most of our lives – and somehow it always burns its way into the songs.”
• The Tom Fun Orchestra won the Galaxy Rising Star Award at the 2009 EMCAs, followed by an award for Video of the Year in 2010. They also won Music Nova Scotia Awards in 2008 for Entertainer of the Year and Galaxy Rising Star.