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Why do bad boys and girls fascinate us? Why do people who thumb their noses at society and sometimes self-destruct capture the attention of marketing and business executives?

I’ve been pondering these questions ever since I saw Dana Anderson of Kraft Foods discuss “The Bad Boys’ Guide to Digital Bliss” April 5 at the Forrester Research Marketing Forum.

Dana riveted the audience by discussing how bad boys like Robert Downey, Jr., and Jack Nicholson can teach marketing executives valuable lessons about living with swagger and embracing the art of being sly. It was fascinating to see an executive from a staid brand like Kraft hold up bad boys as examples for business leaders to follow — and equally fascinating to witness an audience of staid marketing executives eating out of the palm of her hand.

Dana was an excellent presenter, to be sure. But I believe the topic of itself was irresistible to those of us who live in the weeds and wrestle with such weighty topics like how to build our brands with social media. In truth, we love bad boys because they are sexy, they break rules, and they are, well, cool.

Bad boys are sexy

Bonnie and Clyde. King David and Bathsheba. These couples behaved very badly. And their stories are undeniably sexy. According to the Bible (a great journal of bad boy behavior) Bathsheba, the wife of Uriah the Hittite, attracted the attention of King David by bathing in public view of his palace (akin to Monica Lewinsky flashing her thong at President Clinton).

David, a man whose life was defined by bloodshed and passion, promptly seduced her, got her pregnant — and then conspired to have Uriah killed so that he could have Bathsheba all to himself.

Poor Uriah: loyal to his wife, loyal to King David, and apparently far too boring for his Bathsheba and not compelling enough to make David think twice about bumping him off. Uriah is nothing more than a footnote to history. But David and Bathsheba? We remember David as one of the great kings of Israel, and Bathsheba the mother of wise Solomon. They were dangerous, destructive, and sexy.

Bad boys make their own rules

Even the most daring and creative marketers and business leaders live by rules. We have processes for developing ideas. We create our own structures for getting work done every day.

Bad boys fascinate us because they create their own rules for succeeding. They thumb their noses at us, and we reward them with our fascination and interest.

It’s hard to believe now, but in the 1950s, Elvis Presley was viewed as a bad boy. And there would be no modern day rock and roll had Elvis Presley not broken all the rules for how a white entertainer (circa 1954) was supposed to sing and behave. He dressed differently, he sang differently, and he behaved differently.

White male singers were not supposed to dress in gold lame suits and shake their hips on stage. They were supposed to sound like Bing Crosby and Frank Sinatra: safe, romantic, and white. But Elvis broke all those rules (the most important being that he was a white person who sounded black).

Alas, Elvis stopped being a bad boy when his manager Colonel Tom Parker steered his career in the direction of safe, boring movies like Clambake and Harum Scarum. And then for a brief moment in the late 1960s, Elvis recaptured the public’s interest. How? By appearing in a dangerous, skin-tight black leather suit in a memorable Christmas special in 1968 and taunting his fans with a sneer and a swagger. He was a bad boy again – for a while.

Bad boys are cool

Is it the way they embody rebellion? Or is it their ability to laugh at their own bad boy behavior while wallowing in it? I don’t know exactly. But bad boys are cool.

Defining cool is like defining pornography: you just know it when you see it. Jack Nicholson in the 1960s and 1970s was cool. He winked at his fans as he sneered at authority. Robert Downey, Jr., is cool for a different reason: he takes his own bad boy behavior in stride.

On the other hand, Axl Rose and Mel Gibson are uncool because they spew rage (especially Gibson) and try too hard to be “dangerous” (Rose). True bad boys capture our interest because they seem so effortless, natural, and even self- effacing. There is something in us that wants to be cool.

Do bad boys fascinate you? Why? Check out some highlights of Dana’s presentation here and let me know how you feel about bad boys.