Enigmatic entertainer Leon Redbone specialized in music of bygone days

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At the Mariposa Folk Festival on the Toronto Islands in 1972, the stars aligned and shared stages, too. Bonnie Raitt, Jackson Browne, John Prine and Kris Kristofferson performed and mingled. One day, Murray McLauchlan welcomed the unexpected arrival of Joni Mitchell. The next day, Bruce Cockburn graciously split his set time with surprise guest Neil Young. Gordon Lightfoot was around, but did not perform.

Bob Dylan, the greatest songwriter of his generation and a famously enigmatic figure, made an impromptu appearance as well. He did not play, and may not have even been interested in watching the aforementioned stars do so either. Setting foot onshore, the first person he asked for was Leon Redbone, a peculiar Toronto-based specialist in ragtime blues, bygone waltzes and Tin Pan Alley pop. They had originally met at Ms. Mitchell’s house on Vancouver Island.

Photographs from that ballyhooed hippie day show a bandanna-wearing Mr. Dylan posing with Mr. Lightfoot, but also a shot of the Freewheelin’ One with Mr. Redbone surrounded by a crowd. Those two – “long-lost brothers,” the rumour mill churned – left the island with Mr. Lightfoot on a private boat.

Mr. Dylan had famously sung about being a “complete unknown,” an apt description of Mr. Redbone. And although he would go on to achieve musical success and a degree of celebrity status in his long career, the air of mystery surrounding Mr. Redbone never evaporated. He was a man of dandy demeanour, natty wardrobe and a repertoire of whistleable antique music. His musical heroes ranged from flapper-era blues artist Arthur (Blind) Blake to minstrel show performer Emmett Miller. A singer-guitarist with a dry sense of humour and drawling W.C. Fields tone, he carried a walking stick and the bemused expression of a time traveller passing through.

Mr. Redbone died on May 30 in Bucks County, Pa. Retired from performing since 2015, he was 69. A statement on his website was typically fanciful, saying that he had “crossed the delta for that beautiful shore at the age of 127,” and that he had departed this world with his guitar and a “simple tip of his hat.”

His hat would have been either a fedora or a Panama. In his 1970s heyday, when he appeared several times on Saturday Night Live, he favoured sunglasses and a cream-white suit. Conspicuously incognito, Mr. Redbone drew attention by wearing clothes out of era. “It’s not so much a costume, as a consistent way of thinking,” he once explained. “I just see it as a natural extension of what it is that I do as an entertainer.”

Mr. Redbone was laconic and quirky on stage, his nasal baritone delivery as distinctive as a repertoire that ranged emotionally from Irving Berlin’s jaunty Walking Stick to the despondent mope of I Ain’t Got Nobody. Encyclopedic in his knowledge of genteel, old-timey music, he knew his Diddie Wa Diddie from his Polly Wolly Doodle.

Once at the Fiddler’s Green folk club in Toronto, Mr. Redbone sat down at a small table on stage, spread a white napkin upon it and produced a large red tomato from a brown paper bag. After playing his set, he put the garden fruit back in the sack, folded up the napkin and walked offstage. An unfathomable gesture, from an inexplicable performer whose act was shtick of the most sincere kind.

Mr. Redbone was responsible for more than a dozen albums, beginning with 1975’s On the Track, a package of pre-Second World War music with the ambience of an old 78-rpm record. “Redbone, who in his nightclub appearances plays the role of a grinning, almost catatonic folkie, will undoubtedly confound many,” a New York Times review of the record read.

He was not a songwriter. “Champagne Charlie is my name by golly,” he would sing, “and rogueing and stealing is a game.”

In 2016, rocker Jack White’s Third Man Records label released a double-album of early recordings made in Buffalo in 1972. The record was called Long Way From Home, from an artist who went to great lengths to keep his residences unknown and his background a secret.

Backstage at the Newport Folk Festival, a disc jockey asked about his upbringing. “I don’t answer memoir questions,” Mr. Redbone rebuffed. When the interviewer persisted, an electronic pager in the performer’s jacket pocket beeped. With that, the man whose face was obscured by dark glasses, a broad-brimmed hat and a mustache-and-soul-patch combination took his leave.

Mr. Redbone was born Dickran Gobalian in Nicosia, Cyprus, on Aug. 26. 1949. According to a richly detailed and authoritative article published earlier this year in the literary magazine Oxford American, his parents had moved there after their property in the Armenian Quarter of Jerusalem was seized by the Israeli government in 1948. The family later lived in London, the article said. By 1965, the Gobalians had resettled in Toronto.

A self-taught guitarist who was a personification of a windup phonograph, Mr. Redbone was a product of the Toronto folk-club scene of the late 1960s and early ’70s. He was a regular at the Riverboat and, in Hamilton, Campbell’s Coffee House.

If one wished to reach Mr. Redbone during his time in Toronto, it could only be done by placing a phone call to Cue Billiards, a basement pool hall at the corner of Yonge and Bloor streets. “They knew him there as ‘Sonny,’ said guitarist David Wilcox, appearing in a short Canadian documentary released last year about Mr. Redbone. “Or was it, ‘Mr. Charles?’ ”

When Riverboat owner Bernie Fiedler asked for a personal phone number, Mr. Redbone gave him a Dial-a-Prayer connection. At the Riverboat, the hard-to-reach artist was looked after by host Jane Harbury. “There was no understanding Leon Redbone, other than he wanted to do his job,” she recalled in the documentary. “There was nothing more than that.”

Mr. Redbone graduated from coffee-house gigs after Mr. Dylan spoke fondly of him in a 1974 interview with Rolling Stone. “Leon interests me,” he said. “You gotta see him.”

People did see Mr. Redbone – if not on Saturday Night Live, then on The Tonight Show Starring Johnny Carson or as a caricature in a Far Side cartoon or as the star of a Budweiser beer commercial in 1984. (He preferred the Italian beer Moretti, truth be told.)

Other pop-culture highlights included Mr. Redbone performing the theme song for the TV shows Mr. Belvedere and Harry and the Hendersons. More recently, he sang Baby, It’s Cold Outside with Zooey Deschanel over the closing credits of the 2003 film Elf.

What can be gleaned from various recollections is that Mr. Redbone was as fastidious about meals as he was about music. He didn’t like Mexican food, and would eat Szechuan at any time of day. While on tour with Mr. Redbone as a teenager in 1978, guitarist Colin Linden was sized up at a breakfast table in Boston. “You’re not one of those fellows who likes eggs, are you, Linden?”

In 1979, Mr. Redbone survived an accident in West Virginia when a small plane he was in skidded off a runway. Thereafter, he preferred touring by automobile.

His mid-career albums included 1988’s No Regrets, 1992’s Up a Lazy River and 1994’s Whistling in the Wind. He earned his sole Hot 100 hit, Seduced, in 1981.

In declining heath, Mr. Redbone announced his retirement from both recording and performing in 2015. In 2018, a collection of his guitars was listed for sale. Up for grabs were a 1926 Gibson L-3 in three-tone Cherry Burst and the 1930 Martin OM-18 that Mr. Redbone played on the SNL stage in 1977.

In 2011, Mr. Redbone spoke to The Globe and Mail about his puzzling persona. “I’ve been trying to avoid that for all these years,” he explained, when pressed to elaborate on his origins. “There’s nothing dark in my past. I’m just not a very compliant person. My main objective is to promote the music I like, and hope people will find it and are encouraged to listen to it.”

The 2018 documentary on Mr. Redbone was titled Please Don’t Talk About Me When I’m Gone. Respectfully, given his fandom, the request is not likely to be honoured.

Mr. Redbone, who lived in New Hope, Pa., leaves his wife, Beryl Handler, who acted as his manager; two daughters, Blake and Ashley; and three grandchildren.