I don't know when cool became cool. It certainly became a nationwide obsession in the 1950s. My guess is that after a huge number of Americans got a first hand taste of combat in WWII and Korea, the idea of being 'cool under fire', i.e. a soldier apparently unbothered by incoming gunfire, gained a large amount of cultural capital. Certainly, in combat, the ability to attack or face an attack without becoming enraged or terrified, is a survival trait, it's something commanders ask of their troops, troops ask of their commanders and soldiers ask of each other. I think that got changed through a decade of war movies and fiction into the idea that being calm and confident and purposeful in all situations was the ideal, and that over the years was further was changed into the idea that being visibly excited about things was 'uncool'. Furthermore I think there is a difference between cool and hip. The term cool is often applied to novelties in fashion or technology, when a more exact phrase would be 'aesthetically pleasing' or 'new and exciting'.
Gutfield gleefully switches back and forth between definitions of cool as he tries to make whatever point it is that he thinks he's making. It's OK, to examine change with a skeptical eye. The economy and society that supports Gutfield at the trough of wingnut welfare is a contrived and delicate thing. Changing any one of a number of factors might mean that his employer might find it more expedient to toss him out on his ass to fend for himself than to continue to employ such an unpersuasive hack. Some things that might make an employer consider that? breaking up broadcast monopolies like Clear Channel, bringing back 'balance' laws in broadcast news', making news organizations criminally liable for spreading untruths, the list goes on. But at some point one has to draw the line, how much harm is he willing to perpetrate or promote, to earn a living?
To, broaden the scope to Americans in general; there are many of us in a similar situation, in that the only thing that keeps us in our station is the lack of meaningful examination of the American economy and way of life with an eye towards constructive reform. How many of us could afford meat at every meal if all meat produced or imported had to face meaningful environmental, sanitary, and animal care standards that were diligently and vigorously enforced? The American experience is as nice as it is for some people, because other people have to do without or cut corners that the rest of us really think they shouldn't.
Gutfield is sad that conservatives are labeled 'uncool'. He should be pleased as hell to be 'uncool', it's a far more gentle adjective than he and the reactionaries on the far right deserve. It's uncool to work for people who are deliberately trying to disenfranchise American citizens, to destroy regulations on pollution, on, workplace safety, on electoral fundraising, on financial malfeasance. It's uncool to start foreign wars to benefit the bottom line of big defense contractors and oil companies And it's uncool to attempt to pay for all of that by gutting the already threadbare social safety net and to blame poverty on the poor while perpetuating the abuses that impoverish them. But besides uncool, its also, lying, mendacious, malicious, malevolent, pernicious, deceptive, perverted, and sometimes treasonous.
And ultimately, I think that's why we've seen a never ending war on 'hippies' since the sixties. They had the temerity to point out, that the American dream wasn't equally accessible to all Americans. They pointed out the game was rigged in favor of older white christian men, and that every other group was part of a hierarchy of lesser Americans whose influence and power diminished with every step away from white, straight, wealthy, christian or male ideal. They saw that the rules would have to change so that everyone could participate meaningfully in culture and politics and the economy and the academy.
And the for all that conservatives claim to want a meritocracy, that everyone be judged and rewarded on the basis of their capability and contributions, the establishment of a true meritocracy is their worst nightmare. The last thing that the low level shills and propagandists of conservative America want is to have to compete with each other on the basis of results. They are employed as cheerleaders and demagogues to rally the faithful and castigate the unrighteous and to faithfully parrot the alleged merits of unrestricted capitalism (and highly restricted voting) to America. Their job is far more about reassuring their employers than it is about making a convincing argument for lower taxes on millionaires.