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When Chris Flanagan bought a 10-cent record at a Toronto thrift shop about 16 years ago, he wasn't expecting it to change his life forever.

The Australian-born visual artist regularly sifts through old milk crates full of mystery vinyl records to see what gems he can unearth.

Most of the time, he says, the records turn out to be total duds. But when he dropped the needle on a 1970s reggae compilation from Toronto's Monica's Records, he was completely mesmerized by what he heard.

"I was absolutely blown away," Flanagan told As It Happens host Carol Off. "That voice was just incredible and I knew instantly that it was very special."

The song that inspired the documentary Shella Record - A Reggae Mystery. 4:02

That moment sparked a decades-long investigation that took him to Jamaica to meet some of the country's most prolific reggae musicians and producers, all of which he documented for his new film Shella Record – A Reggae Mystery, premiering Monday at Toronto's Hot Docs festival.

'There's not a ton of female singers'

The song, called Jamaican Fruit Of African Roots, features a powerful female vocalist and was credited on the album jacket to an artist he'd never heard of before — Shella Record.

"As a record collector and sort of reggae fanatic, there's not a ton of female singers. So you're kind of fairly familiar with the big names," he said.

"So to hear an incredible voice like that, it was just kind of surprising that I hadn't heard that voice before."

Chris Flanagan in the As It Happens studio discussing his debut documentary Shella Record — A Reggae Mystery. (Sinisa Jolic/CBC)

Both Google and the local music label behind the compilation turned out to be dead ends. So he started doing some real man-on-the-streets, gumshoe investigating.

"I delved into it, you know, digging into Toronto's underground reggae scene, asking people who really should know, and turning up total blanks or sort of rumours and red herrings," he said.

"And, yeah, it did really become an all-encompassing, life-changing obsession over the years."

Shella Record = Sheila Rickards

That obsession led him a local radio station, which played the song and asked listeners to call in if they had any intel.

Then, an anonymous tipster gave him the key he needed to unlock the story: The name was a misprint.

The vocalist who had captured Flanagan's heart is, in fact, Sheila Rickards, a Jamaican jazz musician who was at the height of her career before reggae was even invented.

"It was like, could this incredible roots reggae singer possibly be this sort of early '60s jazz singer who does very different material?" he said. "Is it even the right person?"

Sheila Rickards is a Jamaican jazz musician who performed in the '50s and '60s. (Shella Productions Inc.)

So Flanagan went to Jamaica to find out more.

There, he met famed Jamaican record producer Bunny (Striker) Lee, who recorded the song in 1975.

"I went to Jamaica really with very little information at all," Flanagan said. "I was trying all my contacts to try and somehow get through to Bunny Lee. In the end, I found his number in the Jamaican white pages. So I just dialled the number."

It worked. Just like that, he got through to possibly the most influential person in Jamaica's music industry.

"He invited me over and suddenly I was sitting outside with this legend who produced some of the greatest reggae music of all time," he said.

Lee told Flanagan that Rickards had come into his studio to record one song only.

"She recorded one incredible reggae song and then, as far as he knew, just disappeared," he said.

The studio had been gutted in a fire a few years back, but incredibly, Flanagan and Lee were able find the "partially singed" master tapes from the recording.

"It just felt like another sort of magical link to her," he said. "Even though we hadn't been able to find her, we found traces of her and these sort of elements that she had touched in the making of this remarkable record."

How does it end?

While he was in Jamaica, Flanagan also learned more about Rickards. He tracked down her childhood home and found photos of her in old newspapers.

He also learned from music historians a bit more about the boy's club that was reggae in the '70s, and why very few women who experimented in the genre ever stuck around.

"Sheila was something of a child star, so she'd been primed for a big career from the time she was maybe six years old," Flanagan said.

"So it's possible that she also had less patience for what it took to be a reggae singer — a female reggae — singer in Jamaica in the '70s. So that could possibly explain why there's so few recordings."

AS IT HAPPENS: Hot Docs film explores how colonial education systems fail Indigenous kids

But Flanagan wouldn't say what happens next, or if he ever got to meet Rickards face to face. That would spoil the mystery.

"It was absolutely worth it in the end. I mean, there were definitely times when I kind of despaired and wanted to give up — and I actually did shelve it for a little while because it just seemed like it was going absolutely nowhere," he said.

"Ultimately, I'm very glad that I did persist with the search."

Shella Record — A Reggae Mystery premieres April 29 in Toronto.

Written by Sheena Goodyear. Produced by Jeanne Armstrong.