Sometimes guys just have that kind of personality. As long as they are peaceful and cool guys I don't see anything wrong with being a bad boy.
It's good to just be yourself in life instead of conforming to the average.
Dude, I deal with bad boys on the daily. There is a diff between a bad man and a bad boy, there is more emphasis on "boy". In short, They don't clean up their messes, they rely on their mothers to, mothers meaning wives or girlfriends. Whig why I say they have momma issues. Many times, momma spoiled the shit out of them, they could do no wrong, so when they left, they find a girlfriend to take care of them (typically some boring nice girl or some chick who thinks dating bad boys is cool, but like a child, she must feed it, cloth it, give it moral support and think she can change it). Result=broken homes, pregnancies, drug use, and victim complex in which the bad boy mistakes responsibility for conformity.
I think Jesse is more of man who likes to have a good time, makes his own money, but uses the counter culture as a business model. Dude is quite "corporate".