When did it become cool to be a jerk?

Last night was wonderful. Andy's friends hosted a really cool, laid-back going-away party at their gorgeous house. Tucked away on one of those picturesque old Memphis streets in the vicinity of Rhodes, this house looks like a place where people who let the juices of life dribble down their chins live. I floated in the aura created by beautiful surroundings and incredibly nice people. The folks I met in the initial hours of the shin-dig were eager to introduce themselves, extend a hand, and talk to me about Andy and Memphis and life-stuff in general. As the night grew later, the stragglers began to arrive. Around 11 the person who I will refer to as Douche-bag arrived.

Admittedly, I judged him based on his clothing, but in such a warm and inviting surrounding, I merely expected him to be as friendly as the people I had already met. And then he said what he said. I am not the world's greatest at dialogue, but allow me to recreate.

A brief discription of the characters:
Brad - Recently defended his MA thesis. Laid-back, pseduo-rocker type. An ass to most people, but someone who grows on you after a short time. Brad has had a few beers and the words are a little slow as is the thought process.
Douche-bag - Early 20s, wearing a trucker hat, thick beard, buttoned plaid shirt, nondescript shorts, and obnoxious shoes. He is smoking and nursing the keg, barely leaving the free booze the whole time he is there.

Various chit-chat gives way to the conversation that follows. Several people took part, but the exchange between Brad and Douche-bag is especially significant.

Random person: "Does anyone have any gum?"

Brad (from his perch on the steps): "You know, Bob Dylan hated gum."

Random person: "Well, I like gum, I wish I had some, too."

Douche-bag: "Fuck Bob Dylan. I hate Bob Dylan."

Brad: "Yeah, he hated gum... (incoherent babble about why Bob hates gum).....

Douche-bag: "He's a plagiarist. He stole everything he ever sang."

Brad: "He hated gum and ...."

Douche-bag: "Yeah, I hate him because he is a plagiarist. I hate him for the same reason I hate Martin Luther King, Jr."

Group jaw-drop.


Alright. That is part one. Part two I can just give the highlights. Basically Douche-bag said something like, "You know who the least attractive girl is? The smart girl."

So here is my question with a little explanation. I don't actually believe that this guy meant all of that. I am pretty sure he did it to get a rise out of people (read females) or to get attention. What I want to know is, when did it become cool to be a jerk? Hewas obvioulsy wearing his personna, it was in his plaid shirt and his trucker hat, but his attitude seemed to be put upon as well. In a room full of wonderfully nice people, he was unique for being the jerk. It was like he had to be different and that was the only way. I am going to be on the look out for this behavior. I am hoping this is not a trend.