Whoever wore the first Che shirt was probably pretty cool, and it probably came at a time when wearing such a thing was not advisable, and invited several possible consequences.

During a 2003 visit to a Randy River factory outlet (I needed cheap t-shirts), I found a dozen different articles of clothing featuring that iconic image. Randy River selling Che Guevara – not cool.

While cool has a nebulous definition, it does have its parameters.

The Romantic era is historically viewed as a reaction to the booming population and technological leaps of the industrial revolution. German Romantics established the word zeitgeist, an assessment of cultural climate. Nowadays, using that word (whether you know its meaning or not) somehow makes you cool.

Moving forward a century or two, cool implied a counter-movement to a modernizing world.  The early twentieth century brought us Blues, Jazz, Noir and Bebop. After World War 2, we did our best to move on from the nightmare we had collectively experienced. Frozen TV dinners, the nuclear family and the red scare resulted in Beatniks, Miles Davis, Lenny Bruce and, of course, Rock & Roll.

Since that time, cool has weaved its way in and out pop culture, criticizing our rampant consumerism without entirely shunning it. Up until the 90’s, cool was an elusive thing, a quality the advertising world was very careful about tinkering with. From the 50s to the 70s, a certain paranoia meant that companies stood askance of embracing counterculture, possibly correct in their belief that it wasn’t marketable to their “respectable” demographic. Flying in on the tradewinds of suburbian consumerism, advertising was poorly poised to be considered cool. However, as pop culture became more and more commodified, advertising became aligned with zeitgeist in a way that was acceptable, entertaining and, yes, cool. It’s easy to imagine Miles Davis in an ad today; perhaps as a means of creating mood for a retro-themed product. Product design has even taken up the banner. The Clash have their own themed pair of Converse sneakers – even though Converse would have been hard pressed to consider such a thing in its infancy. Let alone what The Clash would have said in their heyday.

Cool implies being definitively aloof. Take The Ramones, who didn’t care whether you liked them or not. They were cool for being that way, and anyone else who loves them for it became cool by association. It stands to reason then that the 70’s saw the emergence of the term sellout. If you were once cool, and now desired a steady income over cult status, you relinquished your coolness for caring.

Most of all, cool was unavailable unless you were involved in the scene that sponsored it. If you wanted to sport a Clash t-shirt, you’d need to be at their concert, or head to some dingy downtown headshop. Cool lived in unenviable conditions, but in so doing romanticized them. The longstanding link between hardship (economic, political or preferably both) and artistry is a huge part of the groundwork for anything that was ever cool. Hardship was something the man, archenemy of cool, specialized in.

In the mid-to-late nineties, this thing called the Internet came along. The web put cool in a headlock, and gave it a giant, metaphysical noogie. We were suddenly able to access as much information about our heroes as was available. We were able to see just how many other people shared that love, no matter how obscure. In 1997, I was sure I was alone in my fandom of a weird funk band called Weapon of Choice. Several fansites and message boards later and I was in touch with the global WoC community – all of whom considered the scene cool.

Things seem to have spiraled from there. Artists of every kind will use the web to get their names out. The traditional ‘grassroots’ beginnings don’t exactly have the same meaning anymore. If a band uses their shows to add fans to their online community, it isn’t seen as shilling, nor is the band seen as a sellout.

That all being said, current zeitgeist seems to dictate that certain advertising is finally, in fact, cool. Whether Adidas, American Apparel or Apple, brands themselves are now aloof, while being directly in sync with the coolest aesthetic, music, fashion, language and (to some extent) politics. They encompass so much that we consider cool, it almost seems as though they don’t care if we buy their products or not.

Almost.

An individual decision to do without an iPad isn’t much of an issue for Apple, seeing as their marketing alone has millions convinced it’s a product they cannot live without. So it goes for sneakers, phones and video games, too.

Cool has become something altogether different. Once describing someone else’s assertion of identity, it has become something which carries the potential to affirm our own. In truth, cool is attainable for the first time in pop culture history.

The shortest month feels the longest, but nonetheless the posts kept coming. Here are some of the words that made their way onto the Internet.

Scale at the price of brand health? – Jon Finkelstein

A reflective piece about what growing companies can do to keep their internal culture intact and thriving.

The benefits of eating dog food – Steven Hudak

Steven, a developer at Grip, discusses how using your own software can improve productivity and create a better user experience.

How to be innovative – Jacoub Bondre

Jacoub dives into the art of innovation and tackles how to approach problems differently.

Advertising for advertising – Julia Morra

All about advertising an advertisement, where it makes sense and when it falls short.

This post brought to you by… – Warren Haas

Resident hockey enthusiast, Warren Haas contemplates just how far hockey sponsorships will go before fans start throwing in their gloves.

Comment of the Month:

“Autoshows of the future should be concept models only. Leave the production models in the dealership showrooms and give the manufacturers an opportunity to flex their innovation muscles.

Consumers should come to these events expecting to be dazzled by vehicles beyond their imagination; they aren’t interested in buying a ticket to see the same cars they already own and can see on the road every day. And automakers can take the opportunity to showcase their design and tech skills and compete on a basis other than sales.” – Joanna Rolin

In response to: Q+A: What will the Auto Show of the future look like?

Though 37 million people tuned in, last weekend’s Academy Awards saw a 10% decline in viewership since last year’s event. It certainly sparked a lot of buzz, but much of it was confined to 140 characters or less. Yep, I’m talking about Twitter. Could this have had a negative impact on this year’s less-than-impressive turnout?

Let’s face it, when it comes to large televised events like these, you don’t even have to watch anymore. Tired of the hokey announcers? Don’t feel like watching the ads? Show too long and drawn out for you? Get the play-by-play on Twitter just by searching #theoscars. And get it without the celebrity overdose, and often, with a healthy dose of wit.

These massive televised social events generate a whole new type of social event, and it’s happening on Twitter. Connecting with other members all over the world, users are watching, commenting, and tweeting predictions of what’s to come.

With about 200 million accounts out there, and over 1.2 million tweets during this year’s Oscars alone, could Twitter have stolen the show?

Moreover, why aren’t more brands taking advantage of these opportunities? As easily as you or I could join in, so can brands. There’s your target demographic, tweeting about some celebrity’s bad hair. So why can’t [insert hair care brand here] join the conversation?

In the Twitterverse, being relevant is easy. Just forget about selling for a minute, and let your brand’s personality come through. What would your brand say about the topic? What is the topic saying about your brand? With events like this, not only can you reach the same demographic as your TV spot, but you’re practically guaranteed a captive audience. All you have to do is #getinvolved.