Coolness often comes down to how well you handle the uncool stuff that inevitably happens. On the intertubes, that stuff is known by one infamous, universally hated number: 404. Today, we look at those coolest error pages that manage to inject some irreverent fun into all the frustration.

SMASHING MAGAZINE

This lovable big droop extracts an “awww” from even the most cynical and web-raged of us, making us wanna hug him and tell him it’s okay.

GEEK SQUAD

Who can get mad at an awkward know-it-all geek? Okay, plenty of people. But this one aptly walks the fine line between know-it-all self-righteousness and it’s-all-in-good-fun self-derision.

MIXX

In terms of “personality,” Mixx has long been our favorite of the social bookmarking platforms. Their irreverent humor comes through here with both the clever pun and the sheer hilarity of the video.

TWITTER

Most of us have been hit with the dreaded “Twitter down” message. And, come SXSW time or another major live blogging event, we’ll no doubt be hit again. (And again. And again.) But nothing softens the “Grrr!” like a simple image of serene empathy. Bonus points for using pastels to dampen the reds and yellows you’re feeling.

LOOK IT’S ME

This one goes all the way with a flash animation. Watch this little guy as he jumps around, wiggles a reprimanding finger at you, then finally gives up on your obvious idiocy and stomps away.

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There you have it, a cool error page can make the difference between “ugh” and “heh,” and works wonders for fostering that elusive devil’s-in-the-details emotional connection we have with our favorite sites.

We’re actually quite disappointed with the lack of clever 404 pages in some of our favorite, should-know-better web dwellings. (Wired, PSFK and Creativity, we’re looking at you.)