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Advertising executive Syd Kessler.

Syd Kessler made impressions on people. Whether professionally or personally – he was an ad man and one-of-a-kind cat – he made a point of being memorable.

Once, at a Miami hotel in the 1990s, Mr. Kessler and his first cousin Steve Paikin were riding down from the top floor when the elevator stopped. In walked Henny Youngman, the famous Borscht Belt comedian. During the rest of the ride, Mr. Youngman kept looking at the muumuu-wearing giant of a man with a big, red bush-beard standing next to him. That would be Mr. Kessler

At the ground floor, Mr. Youngman began to walk out, but stopped to comment. “Do me a favour,” he said to Mr. Kessler. “Before we all leave, could you rustle me up 10 more commandments?”

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It was a rimshot moment, and indeed, Mr. Kessler did look biblical – “like he’d just seen the burning bush on top of Mount Horeb,” recalled Mr. Paikin, host of TVO’s current affairs program The Agenda with Steve Paikin.

The jingle king of Canadian radio and television commercials was as noticeable and unforgettable as the long-running “Four-three-nine-oh-oh-oh-oh” jingle he produced for Pizza Nova.

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Mr. Kessler, middle balloon. In 1994, he created The Kessler Group to address a growing need in the advertising community to move away from the broadcast advertising model, with its inherent inability to deliver measurable results, to a new advertising model called narrowcasting.

Mr. Kessler died March 7, of complications from a major stroke and myelodysplastic syndrome. He was 74. A maverick, an amateur magician and a member of the Marketing Hall of Legends, he was a burly force of nature and a twinkle-eyed master persuader who did not stand on ceremony. He swore like a longshoreman and shocked the suit-and-tie set with his green velour track suits and moccasins. He offended, delighted and generously mentored people, often all at once.

Mr. Kessler produced memorable jingles including Look Who’s Drinking Pepsi Now, Blacks is Photography, Thank You Very Much Milk, and the music for many Labatt commercials. He was also known for his huge office at Supercorp, a joint venture with John Labatt Ltd. that dominated commercial production in Canada in the 1980s.

Sitting behind an elevated desk, Mr. Kessler ruled every meeting in his office. “The second you walked into the room, you understood the power structure,” said mentee and business partner Jody Colero. “But I knew him before that office, and I can tell you that he controlled every room he was in anyway. He changed the chemistry, the tenor and the language of every meeting.”

According to Mr. Colero, a creative director and film and television music supervisor, Mr. Kessler had the particular skill and inclination to break down a certain kind of person. “People who were impenetrable, he would make a special effort to penetrate. He was going to get to who you were, not the character you were pretending to be.

“He liked the challenge of it, but it wasn’t always good,” Mr. Colero said, “because most people do not want to be exposed.”

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Sydney Edward Kessler was born April 2, 1946, the second son of Hyman and Celia Kessler (née Paikin). His father worked in scrap metal until he died at age 48. Syd was 13 years old, barely bar mitzvahed. He and his older brother, Michael, had to grow up quickly and work to support the family. Working as a railway brakeman and in the steel mills, he failed Grade 10 three times at Westdale Secondary School in Hamilton, Ont.

In the mid-1960s, Mr. Kessler took to California, where his brother had settled. He had a creative side and a passion for music, though he couldn’t read a note of it.

In Los Angeles, he found work at the powerhouse radio commercial production company Chuck Blore Creative Services, beating out future actor-director Albert Brooks and future television executive Brandon Tartikoff for the job.

He thrived as a copywriter, but made little money. “He would live on popcorn and a bucket of Kentucky Fried Chicken for a week,” his son, Jacob Kessler, said.

While in Hollywood, Mr. Kessler developed the successful game show The Crosswits for another production company. He moved back to Toronto in 1971 because of two significant splits: a break-up with his girlfriend and the literally rattling experience of the San Fernando earthquake. “He woke up and said ‘I’m out of here,’ ” according to his son.

In Toronto, Mr. Kessler was a writer for the Wayne and Shuster comedy specials on CBC Television. He got fired from the gig, which might have been the best thing that ever happened to him. “He didn’t like the experience,” Jacob Kessler said. “He decided he would never work for anyone else ever again.”

Mr. Kessler founded Kessler Productions in the mid-1970s. The highly successful Toronto-based company, which created audio production for radio and television commercials in Canada, later changed its name to Kessler Music Inc., a firm Mr. Kessler presided over as as president until 1981.

Though he lived in a mansion and was millionaire by the time he was 30, Mr. Kessler was no suave martini-drinking ad executive. He kept ketchup, mustard and salt in his bedroom, in case he wanted to perk up a midnight snack. He wore sweatpants and T-shirts at home and at the office.

He loved young people. A close friend of business associate Copel (Cubby) Marcus and his wife, Mr. Kessler would visit them and their three teenaged children in the 1970s. Once when the parents were away he took the kids to Woodbine Racetrack. “I had visions of winning hundreds of dollars, but I don’t think I won much,” Jody Davis remembered.

Mr. Kessler would send the kids to neighbourhood houses to conduct market research by reading off a list of questions to whomever opened the door. “He paid us to do it,” Ms. Davis said. “I received a cheque in the mail for 50 cents.”

Mr. Kessler was passionate about magic, going so far as to hire a young magician to teach him.

“He wasn’t childish, but he was childlike,” said Jay Sankey, who helped Mr. Kessler with card tricks and other sleight-of-hand shenanigans. “He was in touch with wonder. You could see it in his eyes.”

His career had ups and downs. In 1994, Mr. Kessler, disillusioned with the direction of Supercorp, sold his shares, pocketing $8-million.

“I was at the peak of my power, and the peak of my powerlessness,” he told The Globe and Mail’s Sarah Hampson in 2000.

Health issues began dogging Mr. Kessler in 1995. There was diabetes, back surgery and depression. “I’d been Superman up until then,” he told The Globe. In 2000, he became seriously ill with diverticulitis and deep vein thrombosis. “The doctor said I was a miracle,” Mr. Kessler said. “I should have died.”

A man of giant ego, Mr. Kessler was humbled by the illnesses. He considered how he had treated people. “Oh yeah, I was a bastard,” he admitted to The Globe.

Robert Armes, who worked with Mr. Kessler in the 1980s, spoke about Mr. Kessler’s tough manner in 2000. “There’s a model that runs through ad culture of guys who end up running companies and eating other companies for breakfast,” he explained. “They have to be ruthless. You have to be a good tap dancer. And Syd has always been a good tap dancer.”

Deeply committed to Kabbalah, a school of Jewish mysticism, Mr. Kessler wrote a self-help book in 2000. The Perfect System was his formula for “finding certainty and fulfilment in the science of life.”

The book, the card tricks, the jingles, the mysticism – it was all about one thing. “He just wanted to delight, and that’s what separated him from everybody else,” Mr. Colero said.

“We’re mortals, and we do silly things,” explained his magic teacher, Mr. Sankey. “The challenge is always to get people to care about this, that and the other thing. Syd could do that. He had a short-cut, which was to pull people to him. That was his magic, and it was real.”

He leaves his wife, Ellen; children Jacob and Isaac; and grandchildren Ariella Sarah, Ana Miriam and Asher Michael.