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Jason Wilson just completed his PhD in history at the University of Guelph.

Deborah Baic/The Globe and Mail

Growing up in the cheek-by-jowl townhouses of Keele and Finch in the 1970s, Jason Wilson couldn't accept that his Scottish-Canadian pastiness was a bad fit with his Jamaican neighbours' music. In a city where the gifts of ethnicity are there for the taking, the budding keyboardist ignored the funny looks and grew up to be a Juno-nominated reggae artist.

So when this genre-bending 43-year-old took the stage at Hugh's Room recently and made the Great War his theme, he naturally went looking for the laughs. Stereotypes about what's appropriate just don't seem to apply.

"People say I'm fearless," he says, with a strong strain of self-denial. "But that's not it. I just don't consider the idea that I'm offending anyone."

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If you want to know about the key role played by female impersonators on the front lines, Mr. Wilson's your man. As the centenary of the First World War approaches, he has devised a tribute show to weird wartime comedy troupes that were the forerunners of modern satire.

Or, as Mr. Wilson puts it in his accompanying book, The Soldiers of Song, "The seeds of black humour that inspired the likes of Monty Python, Saturday Night Live and SCTV were sown in the trenches of the Great War."

Strategists in the war's entertainment division thought they were boosting morale by adding some light musical numbers and demure femininity to the soldiers' bleak routine. But storied acts like The Dumbells, recruited from frontline personnel with a gift for song, dance and sexy transvestism, connected best with fellow soldiers when they found comedy in the carnage.

Mr. Wilson's briskly staged recreation offered a best-of selection from the trench troupers: over-the-top patriotic songs such as Oh It's a Lovely War and the morally loose Everybody Slips a Little mix with foot-tapping ragtime numbers played by his era-appropriate trio (piano, cornet and clarinet) and narrative continuity supplied by Toronto storyteller Lorne Brown.

So why is a reggae artist, even one who wears an ancestral kilt behind his upright piano, so determined to revive the musical stylings of the First World War?

It's a culture clash that captures the essence of a man whose virtuosity is hard to pin down. This summer, he's playing jazz, folk and reggae festivals – he's also partnered with Fairport Convention fiddler Dave Swarbrick on an upcoming reggae-and-folk CD he calls "300 years of rebel music." With Toronto musician Fergus Hambleton, Mr. Wilson plays gigs as The Two Bobs, a Marley-and-Dylan tribute act with the twist that Bob D. sings reggae and Bob M. channels a rootsy style.

Meanwhile he's just completed his PhD in history at the University of Guelph – his first published article was titled "Skating to Armageddon: Of Canada, Hockey and the First World War." From this same passion came his 2008 disc, The Peacemaker's Chauffeur, whose title track is based on a photo from the Paris Peace Conference that he spotted in Margaret MacMillan's book Paris 1919.

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Mr. Wilson's fascination with First World War "concert parties," as the shows were called, comes from the same place as his love of reggae – a desire to get beyond the official narrative and experience a more personal reality.

When he first discovered The Dumbells, he was won over by the strangeness of their wartime theatrics – as if a Blackadder script had been suddenly backdated.

"These are real soldiers. Some of them have been shot and gassed. And then suddenly someone comes along and taps them on the shoulder and says, 'You can sing, can't you? Come with me.' How lucky they were, and how guilty they felt, and how absurd it all was."

Reviving 100-year-old comedy has its challenges. The military slang can elude a younger crowd and there's an air of Britishness that has been diluted in today's Toronto.

But Mr. Wilson isn't troubled: Modern humour, he says, incorporates absurd Britishness via Monty Python, and it all traces back to the dark side of the Great War slaughterhouse.

Where he does admit to being a misfit is when his reputation as "a war guy" misleads some of his students.

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"They talk to me about tanks and machine guns and my eyes glaze over," he says. "That just doesn't have the human stories that The Dumbells do: You're a soldier in this hideous, heinous, surreal landscape that is the First World War and you're putting on a dress to sing falsetto. How bizarre and wonderful that is."

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