One steamy summer afternoon, perhaps seven years ago now, Syd Kessler invited Brett Channer to an impromptu business meeting at his sprawling home on Old Colony Road in Toronto’s upscale Bridal Path neighbourhood.

An enthusiastic swimmer, Kessler had instructed Channer to bring a pair of swimming shorts. Channer figured they’d go for a dip once their meeting was over, but when he arrived, Kessler immediately thrust a pair of inner tubes into his arms and directed him towards the swimming pool. That, Kessler had decided, was where business would be conducted.

Kessler and his wife Ellen, a former copywriter and devout environmentalist, had long before stopped using pesticides on their property, letting nature reclaim the land unimpeded. It meant that the property had become an urban jungle of trees, tangled vines and high grass.

“It was overgrown like you couldn’t believe,” said Channer, chuckling at the memory.

Not even the Kesslers’ pool could defend itself against Mother Nature’s advance. It was covered in a layer of leaves so thick that Channer remembers it looking more like a pond than a powerful status symbol in one of Canada’s most exclusive neighbourhoods.

But there was enough room amidst all of the greenery to accommodate a couple of inner tubes, and Kessler and Channer spent the next couple of hours contentedly bobbing alongside each other while talking business. It was this meeting, said Channer, that would provide the spark for his next venture, the agency Mass Minority.

In many ways, the Kesslers’ house and surrounding property was the embodiment of the untamed and unpredictable spirit, and the prolific mind of the man himself, said Wahn Yoon, who was Kessler’s business partner for 12 years beginning in the mid-2000s—first with Science Intelligence, and later with Wunderkind. “There was just life sprouting up everywhere.”

Kessler died on March 7 at the age of 74, leaving behind his wife Ellen and two sons, Jacob and Isaac.

He was, both literally and figuratively, an outsized figure in the Canadian marketing world—a quick-witted, gregarious and perennially curious man, the very embodiment of the outsized figures who once presided over Canadian marketing and advertising.

The industry has long celebrated its rogues, and Kessler himself lent credibility to its reputation when he posed for a 1980 Toronto Star photo sitting at a mixing desk during a recording session, an exotic bird perched on his right shoulder.

And in a business where personal style is paramount and prized, Kessler’s go-to outfit was typically a well-worn baseball cap emblazoned with the word “Sydney,” complemented by a T-shirt and a pair of track pants.

He was a big, boisterous strong-willed personality who filled any room he walked into, yet those attributes were softened by a deep spirituality, a passion for work, and a love of family.

Friends and colleagues remembered him this week as a larger-than-life figure and creative genius who remained generous and approachable even after achieving the highest levels of success.

His son Jacob, who was also his business partner for the last 20 years, said he’s been overwhelmed by the notes and calls he’s received from some of the many people who knew and worked with his father over the decades. “I always felt I knew what his impact was on others in on the world,” he said, but it was gratifying to see just how many others felt the same way. “He always brought such hilarity and joy and fun to whatever it was he was doing.”

Syd was famous for working long hours, but his family was also incredibly important. “And there wasn’t really a separation of work life and home,” said Jacob. Syd regularly brought home clients and colleagues for dinner, and Jacob remembers doing homework in the studio while his father directed greats like Paul Newman, Jack Lemmon, John Candy and Eugene Levy.

He loved tennis and swimming, and was an amateur magician. “I remember him telling me that he built a very strong friendship and mentorship with [Canadian broadcasting executive] Allan Slaight… because Allan was a big magician also,” said Jacob.

And he was passionate about fishing, which ultimately led to him investing in a TV show called Canadian Sport Fishing, which became one of the top fishing shows in the country.

His father was always a very spiritual person, said Jacob, but around the age of 40 he discovered Kabbalah. “That was a turning point for him, that became a very big thing in his life.”

While he remained a big personality and maintained his voracious appetite for life, Kabbalah also softened him in some ways. “[It] helped him, I think, try to be more self-aware of his behaviour with others,” said Jacob.

Syd Kessler grew up poor in Hamilton, dropping out of the city’s Westdale High School in Grade 10. As a young man he spent some time worked in L.A., where he had a hand in developing a game show called The Crosswits that ran for several years on the ABC network.

Later, after a stint as a CNR conductor, Kessler found his way to advertising and became Canada’s “King of the jingle”—the man behind massively successful advertising ear-worms for the likes of Maxwell House, Pizza Nova, Black’s and countless others (hear some of the jingles below).

At first, his companies bore his name: Kessler Productions from 1974-78, followed by Kessler Music Inc.—which lasted until 1981, when a merger with the country’s two top audio production companies resulted in The Air Company (a trade ad at the time depicted the three principals, Kessler, Rick Shurman and David Beare, as balloons, accompanied by the headline “Meet the Air Heads”).

In 1988, Kessler entered into a joint venture with Labatt to create Supercorp, the company that cemented his reputation and turned him into a true advertising kingpin. Supercorp would become the country’s largest production company, responsible for a reported two-thirds of all the production in Canada (and 2% in the U.S.), its revenues rising from $10 million to $150 million within just four years.

Though he built his career in radio and jingles, he embraced the emerging world of digital in the early 90s and was hired by KPMG in the mid-90s to help run the company’s e-commerce practice. He wrote four books touching on his passions of spirituality, parenting, business and consciousness, and helped launch both Kids Help Phone and the National Advertising Benevolent Society.

He was, said Yoon, the very definition of a renaissance man. Invariably the smartest guy in the room, yet simultaneously curious and eager to learn, Kessler was someone to whom even the most antagonistic clients would defer.

“Irrepressible, brilliant and caring,” says Paula Roberts, the founder and CEO of Halo Brand Leadership, who has spent decades in Canadian advertising. “More than anything, he was about possibilities. He never stopped learning. He was always creating. The true mark of his life is the legacy that he leaves behind—the businesses he built, the books he wrote, the lives he touched. I’m so glad to have known him. He was a remarkable friend and a wise mentor.”

Morris Saffer’s friendship with Kessler goes back nearly 50 years. “He was definitely my greatest, longest and most rewarding creative collaborator,” says Saffer, himself a legend of Canadian retail advertising and someone who worked on countless jingles with Kessler.

Working with Kessler was “insane,” said Saffer. “He was certainly an acquired taste when it came to business, but it worked because he had the skills… He was just a genius at what he did.”

And when Kessler believed in you and your ideas, his support and commitment to making it work was unconditional. “His embrace of what you were trying to do was just wonderful,” said Saffer. “His ability to take our creative branding In words and create the musical sting, and create the musical memories was just magic.”

After first working with him in the early 1980s, when he was the marketing director for American Express, David Kincaid worked closely with Kessler during the early years at Supercorp. Kincaid was director of marketing on Labatt at a time when its flagship brand, Blue, was locked in a protracted standoff with Molson’s Canadian brand for control of the domestic market. “It was all-out warfare,” he said.

One day, Kincaid attended the recording session for what would ultimately be a doomed radio campaign for Blue, where he grew increasingly agitated as Kessler kept doing retake after retake of the voiceover and the mix.

“After about the 400th time, I said ‘Syd, I want to go home,'” said Kincaid. Kessler was sitting on a wheeled cheer, and aggressively pushed himself off from the mixing desk and glided across the studio floor to where Kincaid was sitting. “We’re nose to nose, and he looks at me and says ‘These are the worst radio scripts I’ve ever seen, but I’m going to make them great.'”

Kessler was a study in contradictions, ping-ponging back and forth between extremely quiet and extremely loud. “He had a great eye for big ideas and would fight for them,” said Pirate Radio’s Terry O’Reilly.

“One of the funniest moments happened one day in the late 90s,” he remembers. “I got a call from Syd asking if I was available for a meeting. I crossed the street and made my way up to Syd’s office. When I walked in, Syd was sitting there with two other gentlemen.

“Here’s how Syd introduced me: ‘Terry meet Italo Labignan and Henry Waszczuk. They host a TV show I own called Canadian Sportfishing. Henry and Italo, meet Terry O’Reilly. He’s a terrific writer and he’s going to write your fishing show.

“To which I said, ‘I’m doing what now?’ Too funny. No forewarning, no segue. But that was Syd… He was outrageous in that good way. A legend.”

But Kessler also wasn’t one to bask in past glories, remaining perpetually focused on what was next. Yoon remembers a meeting at Kessler’s house (no pool this time) when the two were attempting to get Wunderkind off the ground. He needed a new notepad, and Kessler told him he’d find some in a downstairs storage room.

While poking around in closet, Yoon came across cardboard boxes full of creative awards. “I have never seen that many creative awards in one place in my entire life,” recalled Yoon. “I said ‘Why do you have them in boxes in a closet in your your basement?’ I mean, any ordinary creative director would have them on giant shelves in the [agency] lobby. He looked at me like I was crazy and said ‘Why would I, that’s in the past? We’re on to the next thing.’

Edie Weiss, president and CEO of Radke Film Group, got to know Kessler on a deeply personal level when he would use the production company’s boardroom for client meetings. “He had the same effect on me as he had with others, of being a person you wanted to be around,” she said. “I just needed and wanted his presence in my life, somebody who I considered to be an elder and a mentor.”

Weiss remembers being captivated by Kessler’s candour, his willingness to talk about when things went wrong as much as when they went right. “When you hear stories of self-reflection, it allows you to begin to look at how you can change your own story,” she said.

This week, Jacob Kessler provided The Message with several pictures spanning his father’s career. Taken together, they present a portrait of a massively successful life and career: a snapshot with the late Robin Williams; proudly displaying the catch from a fishing expedition; a trade magazine ad announcing the launch of a new business venture, etc.

But there is one picture in particular that feels particularly evocative. It shows Kessler sitting with another Canadian ad legend of another time, the late Gary Prouk, at an industry event. The two men are sitting literally inches apart, staring intently at each other, an improbably large centrepiece in the foreground.

Prouk looks as imperial as ever, a half-smile playing across his lips; Kessler, meanwhile, has his hand on Prouk’s arm as if attempting to convey a thought of the utmost importance. It is nothing more than a mere glimpse of a moment in time, yet it somehow feels like a snapshot of a fast-receding era: two former titans of advertising, with no sense of their legacy and imprint on the industry.

—With files from David Brown