My Last Argument with Jim Riswold: Creativity vs Interestingness

I was intimidated by Jim Riswold when I worked at Wieden+Kennedy. The man was a legend—an intellectual giant whose brilliance in advertising was indisputable. I’ll never forget the rubber stamp he kept in his desk, emblazoned with the word "stupid," reserved for work that didn’t meet his high standards.

As a young planner (strategist) at W+K, I often felt like I was in way over my head. I was acutely aware of how little I knew about advertising, and Riswold’s sharp wit only magnified my insecurities. I remember one instance when I was working on a brief for cross-training. My boss sent me to Jim to ask what made cross-training so successful the first time. His response? "Marketing," delivered in that succinct, almost dismissive way that only Riswold could pull off. He was, of course, referring to the legendary "Bo Knows" campaign. And while that conversation didn’t immediately help with my brief, it made me reflect deeply on what made that campaign—and others—so effective.

Fast forward twenty-five years. Though still somewhat daunted by his intellect, I found myself sitting in Jim’s apartment this past April, discussing advertising and the concept of "interestingness"—a framework Jeffre Jackson and I had been developing to better understand the impact of great advertising.

When we sat down to discuss the idea, Jim greeted the term "interestingness" with characteristic skepticism. To him, it sounded too intellectual, too analytical—a term that seemed to miss the visceral, gut-level impact that great advertising should deliver. He preferred to describe his work with a simpler, more familiar word: creativity. But as we went through his body of work, it became clear that Riswold had done more than just create. He had crafted some of the most compelling ads in the history of advertising—campaigns that demanded engagement, sparked thought (and sometimes anger), and embodied the very essence of what makes something truly interesting.

Why "Interestingness" Matters More

"Creativity" is a term that, while valuable, can be somewhat nebulous. It suggests originality and imagination but often lacks depth when it comes to explaining why something resonates so profoundly with an audience. "Interestingness," on the other hand, goes beyond mere originality. It’s about the effect an ad has on an audience—engagement, connection, and the ability to hold attention and provoke thought. It speaks not only to the novelty of an idea but to its capacity to sustain interest and evoke a response.

The pairing of the fictional character Mars Blackmon and Michael Jordan in the "Spike and Mike" campaign was not just a creative move; it was a masterstroke of incongruity. The unexpected dialogue between an MJ superfan and an athletic icon created a dynamic that was both surprising and captivating, making the campaign unforgettable.

Charles Barkley’s blunt declaration, "I am not a role model," wasn’t just a clever line; it was an authentic expression of his true feelings. This authenticity was compelling because it came from a place of truth. It wasn’t an attempt to be shocking for attention’s sake—it was Barkley being who he was, without pretense. While the ad stirred up controversy and discomfort by challenging the conventional expectations placed on athletes, it wasn’t just about being creative; it was about evoking a complex emotional response that made viewers think, argue, and feel. The ad’s ability to provoke mixed emotions—anger, agreement, disappointment, and relief—gave it a depth that pure creativity might have avoided.

What made "I Am Tiger Woods" truly compelling was its significance. By having people of all ages and backgrounds proclaim, "I am Tiger Woods," the campaign transcended the mere promotion of a sports star. It became a meditation on identity, aspiration, and the universal drive for greatness. This deeper meaning is what made the campaign memorable, showing that interestingness, through its emphasis on significance, goes beyond creativity’s surface level.

In "Barkley on Broadway"—an ad Jim told me was the closest he ever got to a perfect ad—every element was meticulously crafted to create a rich, engaging experience. From the costumes to the choreography, to the juxtaposition of violence and water ballet, to Chuck D rapping under Barkley’s lip sync, every detail was considered. This attention to detail transformed the ad from a simple promotional tool into a piece of entertainment. The richness of the craft invited viewers to appreciate the layers of effort and creativity that went into its production. While creativity might celebrate the concept, interestingness recognizes the importance of these details in creating something truly memorable.

In the end, while creativity is an essential component of any great ad, it is the qualities of interestingness that truly capture what Jim Riswold’s work (advertising and art) has always been about. Interestingness isn’t just about being new or original; it’s about depth, authenticity, emotional and intellectual engagement, and attention to detail. It’s about creating work that doesn’t just catch the eye but stays in the mind, provoking thought and conversation long after the initial viewing.

Riswold’s ads aren't just creative; they engage, challenge, and resonate on multiple levels. In a world overflowing with content, it’s this kind of interestingness that cuts through the noise and leaves a lasting impact—just as Jim Riswold’s work has done for decades.