For a period almost as brief as Olli Jokinen’s career with the Maple Leafs —six games in 2014-15 — Tiny Tim found a substantial following in the late 1960s. Born Herbert Khaury, Tiny Tim was a curious looking figure with long, straggly hair, wearing an ill-fitting suit while singing Tin Pan Alley songs from the 1920s and 1930s in a falsetto voice accompanied by a ukulele that he carried in a paper bag.

The entertainer was truly original. His recording of “Tiptoe Through the Tulips,” a song that had already topped the charts for Nick Lucas in 1929, rose to the top 20 in 1968, and made Tiny Tim a sensation. He appeared regularly on television shows such as Rowan and Martin’s Laugh-In and The Tonight Show.

A devoted baseball fan, Tiny Tim discovered his love for hockey quite by accident. He told Weekend Magazine in 1968, “I said to myself, ‘I wonder what I can do to keep myself active in the off-season?’ Basketball and football didn’t click with me. Then, I saw an ad for hockey at Madison Square Garden. It was love at first sight.”

The eccentric New Yorker became a diehard fan of the Maple Leafs. In 1945, while scanning the radio dial, he discovered Foster Hewitt broadcasting a Leafs game on Hockey Night in Canada. “I wanted to have a team so I looked at the standings in the newspaper and there were six teams to pick from. Maple reminded me of maple syrup and Leafs reminded me of the tree leaves, and it all reminded me of nature, and I like that, so I chose them.”

Before “Tiptoe Through the Tulips” caught the public’s attention, Tiny Tim’s act drew the derision of crowds in the seedy New York bars in which he played. “They used to throw things at me,” he recalled. “But I was like Mr. Sawchuk. I had my ukelele for a goalie stick. I used to bat away the pucks just as they were shot at me.”

He considered himself a goalie at heart. “I once bought an official hockey puck. I used to bounce it off the wall of my room and catch it and pretend I had made a great save off the stick of Mr. Bobby Hull. If I had one final dream, it would be to put on the goalie pads someday and have someone shoot at me like Mr. (Jean) Beliveau or Mr. Bobby Hull or Mr. (Tim) Horton. It would be such a thrill!”

During the 1964-65 season, Tiny Tim attended every home game of the New York Rangers. His unmistakable presence garnered no end of abuse from the fans at Madison Square Garden. When Toronto was in town, Tiny Tim would wave a Maple Leafs pennant. “I’d stand up and shout, ‘Come on, Leafs!’ The fans used to throw beer at me. They would shout, ‘Get that witch and keep him quiet.’”

Through good times and bad, Tiny Tim rooted for his Maple Leafs. He had his favourites, too. “That Mr. Horton; a wonderful player. And have you noticed that Mr. (Johnny) Bower? You just can’t beat him in the last five minutes of a game in which the Leafs are ahead.”

In June 1969, Tiny Tim was on a bill at the Toronto Pop Festival with Alice Cooper, Ronnie Hawkins, Sly and the Family Stone, and the Velvet Underground. He returned to Toronto on Oct. 7 that year for an appearance on Hockey Night in Canada. This time, Tiny Tim got the opportunity to meet his beloved Leafs. He pulled on Pat Quinn’s sweater and skates and, prior to an inter-squad charity game, tried skating for the first time. Much to the delight of fans, Mike Walton and Jim McKenny held him up as he attempted to take a stride or two on the ice at Maple Leaf Gardens. One reporter wrote that Tiny Tim “wobbled across the ice on legs like tapioca pudding.”

Tiny Tim smiled and brushed the long, stringy hair from his face, which was caked with heavy white powder and red lipstick. “What a thrill! Just being on the ice was great!” He wasn’t overly disappointed that he wasn’t able to skate, admitting, “I was always athletic spiritually, not physically.”