There's a moment in every kids life when their parents, for no explainable reason, decides that it's time to "act cool" and show their children that they too are "hip." All of a sudden these middle aged bores start to do the unexpected, they'll hang out at the mall, start liking rap music and begin using recent slang. But it doesn't work, all it does is make the adult look foolish and embarrass their offspring. But they'll do it anyway; they think it's a way of connecting with their rapidly aging children or a way for them to stay youthful. Lenny Bruce said it best: "There's nothing sadder than an old hipster."

Now imagine that your mother or father is actually Microsoft and trying to court the game-playing public. They know that the average gamer isn't going to be impressed with middle-aged men who have spent their whole life refining operating systems and office programs, no teenager is going to be excited by a group of guys who once wore pocket protectors and looked like rejects from Revenge of the Nerds. The average gamer wants somebody cool, they want somebody they can relate to. Unfortunately it's hard to pretend that you're hip, especially if you're an old hipster like Microsoft.

Ever since introducing the Xbox brand back in 2000, Microsoft has done everything it can to look and act cooler than they actually are. That's not to say that the staff at Microsoft are a bunch of squares or anything, but when you think of Windows, Internet Explorer and Works chances are you don't say to yourself, "man, I bet that's a cool group of cats I'd love to hang out with." Instead you probably picture these Washington-based employees counting their money and stock options, laughing at all of the people who just a few years ago told them they were throwing their life away making computer applications.

Perhaps Microsoft knows this, because every step of the way they've done everything they can to project the idea that they are the coolest company on the block. How else do you explain the early photographs of the Microsoft staff riding skateboards and dropping mad lingo? From day one the Xbox team wanted you to know that they were cooler than Nintendo, Sega and Sony, and if that meant they had to show you that they could bust a move on their board, drop some phat slang, or show utter contempt for "the man," then that's exactly what they were going to do.

The idea of J Allard (who is too cool to use his first name, James) grabbing his skateboard and having the mainstream press snap pictures of him pulling off tricks is almost too stupid for words, yet that's exactly what happened. But if you think that J Allard's stunt was ridiculous, then the fact that other Xbox team members decided to do the exact same thing may be enough to make you never want to turn on your Xbox 360 again. There's nothing sadder than seeing a bunch of thirtysomething's prove that they are as cool as Bam Margera. And you can tell that they are cool, because they opted against the kneepads and protective helmet.

It would be one thing if J Allard tricking off his skateboard in the pages of Electronic Gaming Monthly was a onetime thing, but over the last seven years we've seen this Microsoft crew do everything it possibly can to act cooler than it actually is. One need not look any further than the way they introduced the Xbox 360 to the public.

Instead of going for the traditional introduction (done at some pre-E3 press conference), Microsoft decided to unveil their Xbox 360 on MTV. That's right, MTV. In the thirty minute infomercial Microsoft showed off the hardware, gave us lots of shots of celebrities playing with the hardware, injected some MTV vee-jays to talk about the hardware, and wrapped it all up with the flavor of the month, The Killers, singing their big hit while MTV flashed pictures of the hardware. Despite the fact that this was a show about the Xbox 360 launch (and the first time most of us had seen any Xbox 360 games) this MTV special offered only a minute or two of actual gameplay air time, instead focusing on the musicians and celebrities. Knowing MTV's style I can't say that surprises me, but as a gamer wanting to know more about the games I would have to say that Microsoft's attempt to be hip fell on deaf ears. At the end of the day it just seems to be a major embarrassment for everybody involved.

Unfortunately this pathetic play for MTV's "hip" audience wasn't just confined to some lame thirty minute infomercial; instead Microsoft actually took some of this supposed style and used it at that year's E3 press conference. In an attempt to set themselves apart from the tucked-in shirts at Nintendo and Sony, Microsoft decided to dress J Allard up in a casual hoodie and send him on stage to convince gamers everywhere that you just couldn't be cool without an Xbox 360. To do this J Allard actually sat down on the stage and delivered his talking points from a relaxed position. While it's not exactly J Allard tricking off of a skateboard, the fact that he sat down during a professional press conference certainly gave off the impression that Microsoft was hipper than their competition (who, for what it's worth, stood up for their press conferences).

And it's not just J Allard who is trying to prove that he's cooler than his counterpart and Sony and Nintendo. Just look at Peter Moore, who back in 2004 announced that he had a Halo 2 tattoo advertising the November 9th release date. What takes this story from being mildly silly to downright creepy is the fact that he actually did have a tattoo promoting the release date of Halo 2 ... and he wasn't afraid to show it to everyone that asked. Three years later he announced the same thing, only this time he had tattoos of Halo 3 and the recently delayed Grand Theft Auto IV. While it's clear that Peter was hoping these tattoos would make him (and by default his company) look hip, part of me just feels sorry for the guy (and his wife). Here's a middle aged man who is spending the peak of his career getting game logos tattooed to his body in hopes that it stands out from the rest of the pack. Worse yet, only three years after showing off his Halo 2 tattoo, Peter announced that he's leaving Microsoft in order to head up the EA Sports division.

Clearly some people at Microsoft are able to pull off that "cool" attitude better than others. While Peter Moore definitely went over the top to prove that he's psyched about those big Xbox games (Halo, Grand Theft Auto, etc.), it's J Allard who seems to be the go-to man when Microsoft needs somebody to make them look cool. Unfortunately sometimes that coolness runs aground and J Allard comes off looking less like Al Pacino and more like "Weird Al" Yankovic.

J Allard knows that there's nothing cooler than making a bet with video game journalists ... unless you accidentally lose the bet and have to wear giant dreadlocks to make you look like the whitest man in Jamaica. That's exactly what J Allard did when he bet Newsweek editor N'Gai Croal that the Sony PSP wouldn't outpace the PlayStation 2. Well, it did, and J Allard was forced to take a picture of himself sporting dreadlocks. Of course, this is considerably less cool than the original bet, where "Allard would wear a dreadlock wig for the entire month of May, including the week of E3 2006." But what can you do?

This may be the first time in seven years that somebody connected to Microsoft hasn't gone out of their way to look as cool as possible. Perhaps this is a promising sign that the makers of Xbox have decided that "cool" is what you are ... not what you try to convey. Cool cannot be forced; it's not getting a tattoo or doing skateboarding ticks. You can't fabricate cool, it's not something a twenty million dollar ad specialist can pull out of thin air. Cool is a state of mind, it's a perception from the game playing audience. And the sad truth is that if you're old and you're trying this hard to be hip, then buddy, you're never going to be cool. You're just going to be that old hipster that everybody makes fun of.