America loves and hates bad boys.

The media vilify and attack small transgressions.

Take Howard Dean. He wasn’t even a bad boy and the media destroyed him after he expressed too much joy and he went from first place to no chance.

Yet others who break more stringent rules become icons—in fact, some of our most highly regarded and lauded.

Why the difference? Why did Howard Dean go down while others rose to fame for less forgivable behavior?

Successful bad boys

Let’s look at some of America’s highly regarded bad boy icons and see why some men who seem to break our society’s most stringent rules, instead of suffering in the public eye, rise.

I’ve written about Charles Barkley, who threw a man through a plate-glass window in a bar fight. He remains a respected sports commentator decades later. Why? Because people like to hear his thoughts.

Hugh Hefner flaunted sexual constraints of his time. Many called him sexist but many loved him. He created one of the best known brands ever. Whoever his critics were, he survived them while nobody knows them anymore.

Andre Agassi’s style in tennis doesn’t look as bad boy by today’s standards, in large part due to his influence, I’d bet. Tennis dressed conservatively and he did what he wanted. Many called him the “Bad boy of tennis,” and people loved him.

James Brown used drugs and got caught. We also call him the Godfather of Soul and rank him as one of the greatest artists of the twentieth century.

Same with Keith Richards. Here he is when he was doing heroin in 1977. Heroin! Everyone regards him as one of the greats.

Who compares with James Dean among male icons? Here he is with the car he crashed, endangering others.

Marlon Brando compares with James Dean. Here he is in what people at the time must have considered contributing to teenage degeneracy or whatever they called it then. Now motorcycle jackets are normal but I don’t think they were then.

Finally, how about Michael Jordan. He has a pretty clean image, even not counting the gambling. Here he is, though, smoking a cigar.

Despite his generally clean reputation, I think he qualifies as a bad boy. He intimidated others. Today people try to make movies where people smoke R-rated but Jordan smoking didn’t tarnish his image. I think it added to it.

Bad boy failures

My first idea to search for pictures of failures for bad boys was too successful. I searched “meth addict male,” and most of the images made me too uncomfortable to post. Here is a relatively mild one. I hope for his sake he enjoyed his experience while it lasted because I think anyone would call him, at least at the point of his second picture, a failure.

I presume while he took meth he felt like a bad boy, but I don’t think anyone would look up to him, even if his physical condition didn’t degenerate like it did.

What makes the difference?

Why do we not excuse the meth addict but celebrate Keith Richards, who everyone knows used heroin?

Why do we celebrate Barkley despite his violence, but not excuse Howard Dean?

I believe the bad boy image works when the underlying person has reached success through such disciplined work that no one can question their stability. I haven’t met any of the examples I gave so I can’t say for sure, but I understand they all practiced their crafts to reach the peaks of their fields. I suspect they never stopped, even when they were being “bad” outside of their professions.

That is, they never messed with their craft. They always respected and kept at it. I have a feeling Keith Richards always played guitar, even when he was doing drugs most. I haven’t read his biography, nor do I know much beyond his Wikipedia page, but I know he plays guitar almost without peer, and I believe that skill only comes through practice and rehearsal, and practicing and rehearsing enough to be the best in the world means stability.

Same with Charles Barkley. He would put on weight but I don’t think he stopped practicing basketball.

The meth guy probably felt great for a while, but he looks like he let his life go. I can’t imagine he had discipline creating stability. I don’t think the successful bad boys had that lack. Howard Dean was close to becoming President, but what disciplined background did he have? I don’t think politicians have discipline that they practice.

If you go back to a statesman like Malcolm X, you find a bad boy who spent time in jail. But he emerged to global prominence. Anyone who was around when Spike Lee and Denzel Washington’s movie about him came out knows many still love him.

I think people who love him know that after his jail time he made his life incredibly disciplined.

Again, I think that lifelong discipline and dedication makes the difference. Be a bad boy without it and you’re a loser. With it, you can succeed.

Just my thoughts on trying to resolve an apparent paradox.

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