The tireless songwriter — who once told The Canadian Press that he'd written 260 songs in his career, "all about Canada" — penned tunes about "gettin' stinko" in northern Ontario mining towns ("Sudbury Saturday Night"), about Manitoban heroes of the First World War ("Wop May") and about prospecting for riches in the deep north ("Long Gone to the Yukon").
He was the rare homegrown star who stayed home. And he doggedly urged his fellow Canadian songwriters to continue chronicling the stories tucked in each corner of this sweeping land, even if it meant a diminished place in an industry that often has its eye toward the U.S.
"He was a true original," said former EMI Canada president Deane Cameron. "He was a storyteller-troubadour and a tremendous promoter of the Canadian identity in a very down-to-earth, storyteller kind of way."
The death of Connors on Wednesday at age 77 touched off a flood of remembrances across the country, including public tributes from the likes of k.d. lang, Bryan Adams and Margaret Atwood.
From hockey coaches, to friends and cherished musical peers, scores of Canadians took a moment to pay tribute to the one-of-a-kind songwriter.
"Stomp on Stompin' Tom," wrote lang on Twitter. "May you have a swift rebirth. Thanks for shedding some light on our selves and our Canadian culture."
Folk singer/songwriter J.P. Cormier met Connors back in 1990. A fledgling musician, Cormier was 19 years old at the time and completely broke.
Cormier had grown up "really, really poor," just like Connors, who lived hand-to-mouth as a youngster, begged on the street at age four and hitchhiked across Canada at the ripe age of 12, snapping up odd jobs as a grave digger, tobacco picker and fry cook.
The multi-instrumentalist Cormier was hired by Connors as the utilityman on his comeback tour. Starstruck, Cormier went to Connors' house and the country legend sized up his duds over the kitchen table.
"He said: 'Go to town and get some clothes for the tour.' And he handed me in 500 dollars in cash. When he put it in my hand, I started crying. And his wife looked at me and said, 'What's wrong?' I said, 'This is the most money I've had in my hand in my life.'"
Eventually, Cormier says Connors "became like a father to me." And he said that Connors' insistence upon writing about Canadian cities and people, rather than chasing riches Stateside, was a sadly unique position for a marquee Canadian artist.
"He tried so hard to get us to embrace our own country and our own ways, and not take on the ways of the Americans and the American industry. He tried so hard to get us to do that. And frankly, nobody has. Nobody's done it," said Cormier.
"He was so unique — he could have easily been a (Grand Ole) Opry character. There's no question that he could have done that. He could have went down and written about America and about the same things that they wrote about. He chose not to do that."
Nova Scotia folksinger Dave Gunning's relationship with Connors dates back to 2002, when he was hired to play upright bass on his tour.
But his history with Connors goes back longer than that.
When he attended Saint Mary's University in Halifax in the early '90s, the two most popular bands to soundtrack floor parties were Connors and the Tragically Hip.
He learned about Canadian history through Connors' music, listening to the black-hatted performer's gritty voice hum about the Frank Slide disaster in what is now Alberta or tobacco farming in Tillsonburg, Ont.
"Remove Stompin' Tom from the equation, and Canada would be a much more boring place," Gunning said in a telephone interview.
"He's truly ours, and only we can truly understand it. He never really left the borders too often. He loved Canada."
In an interview with CTV, another Canadian icon — Gordon Lightfoot — remarked on Connors' astonishing output, singling out "The Hockey Song" in particular.
"It really is a powerful song to hear onstage although it is a very light-hearted song," said Lightfoot.
"He was a powerful entertainer and he had a powerful voice. He was a great player, he always had great musicians working with him."
Cameron, meanwhile, noted that Connors was an inspiration to other musicians because of his commitment to his musical vision.
"He was a man of conviction, everybody knew that he stood for certain things, Canadianism being at the top of that list."
Indeed, Connors sometimes seemed to be on a mission to preserve a collective passion for Canadian storytelling.
Gunning and Cormier both consider themselves to be following in Connors' lineage, writing honest, unadorned songs about Canadian history. Both say they were personally inspired by Connors to do so.
He encouraged other young musicians when he could. Juno-winning country singer Corb Lund says Connors used to pass on congratulatory messages through a mutual friend. Connors brought Calgary country singer Tim Hus on tour with him and trilled his praises to journalists whenever he had the chance.
But while they and others carry on Connors' tradition, none possesses his considerable profile.
And that's, in part, because the notion still exists that writing overtly about the Canadian experience has a debilitating effect on an artist's commercial prospects — both inside and beyond our borders. With Stateside success looming as an increasingly essential element for Canadian musicians, young artists are dissuaded early on from branding their tunes with a figurative Maple Leaf.
"When I was younger, especially in the genre of country music, I felt that I couldn't necessarily sing about Canada without taking myself out of the mainstream — that if I sang about a Canadian theme or location, that it would put me at the edge of my genre," said two-time Juno nominee Dean Brody in a telephone interview Wednesday.
"He was one of the guys who said, 'I don't care. I'm going to sing about my country. I'm going to sing about what I'm proud of. I'm going to celebrate our existence as Canadians.'... It just was a passion for him.
"That's what I deeply respect about Stompin' Tom."
Connors said in a 2010 interview that his method for finding inspiration was taking long, silent drives through Canada in his SUV, without the noise of the radio to distract him. He kept a notebook stashed at his side to jot down any observations he made along the way.
Even as he stayed resolutely faithful to his philosophy of capturing Canada in song, Connors frequently lamented his lack of radio play and wished aloud that more Canadian musicians would stay here, even after hitting it big.
Given that even the plain-spoken Canuck star sometimes struggled to find mainstream recognition, it seems unlikely his unique brand of Canadian-focused folk storytelling will find continued prominence with a talented but lesser-known generation of songwriters determined to carry on his legacy.
"I think it's been lost — it was lost long ago," Cormier said sadly. "That's the saddest part. We really have to start being proud of who we are, and stop measuring ourselves against everybody else.
"Canada is just filled with talent. And we have to stop measuring our success against anybody — Americans, Europeans.... We have to start embracing ourselves."
And Cormier is hopeful it could happen.
"I'm sure as time goes on now after he's gone, we're going to start realizing the value of what he did, more and more and more," he said.
"I think other artists will also follow in his footsteps more closely when they start to realize what he left behind for us."
Note to readers: This is a corrected story. An earlier version wrongly said Connors died Monday.