When it comes to marketing, almost nothing can surpass “coolness.” While trends vanish, and hip is for hipsters, coolness can cut through almost any demographic. It’s why everyone loves TED talks and no one disses the Beatles without looking utterly foolish.Paid content is not cool. At least not yet.Those of us in the business meet skepticism and outright disdain from time to time. But comedian Louis CK’s recent online success may be an inflection point in the “paid content x coolness” bell curve. Through humor and honesty, CK gambled his crop of jokes by posting them online for viewers to download for $5. He didn’t put any restriction on how they could view it — a move that’s usually ripe for torrenting.However, he made an impassioned and funny appeal (laced with a bit of profanity) explaining his production costs and reasons for charging (i.e., feeding his wife and kids).In four days, he collected $500,000 in revenues, and claims to have made $200,000 after expenses (his math is a bit fuzzy). He’s also added attitude and grit to best practices — his “Add to cart” button says “Buy The Thing”. Talk about knowing your niche.Of course, we’ll have to wait and see if CK is able to continue reaping dollars months from now. Loyal fans who visit CK’s site may be willing to fork over $5, but a wider audience may not. And CK could have saved money by ditching PayPal and going through more traditional payment processing gateways. But it’s an interesting experiment to keep an eye on.Because it’s Friday and you’re probably looking for a way to procrastinate at work, here’s a free outtake to view (warning: some profanity and explicit language… but still very funny). Enjoy!