Humor has always been an effective staple in advertising, but the IT industry --historically, at least--hasn't exactly been a fountainhead of ad humor. There have been some exceptions, of course, but I'd challenge anyone to name an advertisement from an IT vendor that matches the humor of such popular classics as Reebok's Terry Tate "pain train" spot, Budweiser's King Crab segment, or the cat herding cowboys from EDS.

Part of that can be traced to the nature of the industry itself: certain types of humor tend to be funny to people in a certain industry, but draw puzzled stares when people outside the industry are exposed to them. I'll chuckle at geek humor as much as anyone, but there hasn't been much to laugh at over the last few years. That's thankfully changing, with a number of vendors (from Microsoft to Apple) bringing some quality humor to their product pitches.

So in honor of today being a Friday (and of the upcoming Super Bowl, which always features a wealth of rib-tickling TV ads), I've assembled a "Top 5" list of old and new IT ads and video clips (listed in no particular order) that manage to do a respectable job of bringing some humor to IT marketing. Some of these bits likely didn't start out intending to be funny (the second Steve Ballmer spot comes to mind), but you have to admit they're funny. (They made a geek like me laugh, anyway.)

1. Steve Ballmer Sells Windows 1.0 (Except in Nebraska)

Selling Windows 1.0 in an infomercial format likely seemed to be a good idea at the time, but the actual execution may leave something to be desired. In this internal Microsoft clip taped in the 80's, Microsoft CEO Steve Ballmer is seen vociferously extolling the virtues of Windows 1.0. For a more recent example of Ballmer promoting Microsoft and its wares, a second clip shows the executive from Redmond skipping and shouting as Gloria Estefan blares in the background. Who says that Microsoft doesn't have a sense of humor?

Link: Selling Windows 1.0
Link: Dancing to Gloria Estefan

2. Apple, Ellen Feis and Kevin Costner

Sure, the recent Apple ads featuring a portly, clueless (albeit endearing) PC being upstaged by a cool (and annoyingly hip) Mac are blanketing the airwaves these days. But does anyone remember the infamous Ellen Feis Apple spot? The aforementioned Feis is seen blearily discussing her admiration for Apple, leading to speculation that she may have been under the influence of something other than Apple's marketing department when the ad was taped.

Want more? Older Windows IT Pro readers may recognize a young Kevin Costner serving as a small business owner in an ancient Apple Lisa TV spot.

Link: Ellen Feis Apple Ad
Link: Kevin Coster Apple Lisa Ad

3. When A Daddy and a Mommy Love Each Other Very Much...

Microsoft has made some strides on the humor front over the years, as this link to a mock Windows Home Server site can attest. Herein, a fictional children's book author explains the benefits of Windows Home Server to a young reading audience, describing office servers as "boring machines using by big people." There are even funnier bits, including a section about what can happen when parents "love each other very much". Who knew that Windows Home Server could improve basic reading skills as well?

Link: Windows Stay-At-Home Server

4. Intel's America Idol
While recent headlines may have given Intel a more boorish appearance than their PR department may prefer--witness their dumping on the OLPC project (and by extension, millions of poor kids) and recent legal woes in New York--they still have managed to inject some humor into their IT marketing with their recent music video for the vPro processor series. Pitting a Michael Bolton-esque crooner against Heavy Metal rockers, this ad spot (directed by Christopher Guest) shows that even chip makers know how to get a laugh.

Link: Intel vPro Music Video

5. The Lone Server
Finally, Microsoft's forthcoming release of Windows Server 2008 is off to a good comedic start, thanks to a smart (and funny) campaign that humanizes the "last Windows Server 2003" at Microsoft. There are lots of geek inside jokes here, ranging from the blue screen of death (a drink mixed up by a barkeep to "make you forget everything") to the fate of the derided Windows ME OS (now consigned to washing dishes and clearing tables). It's a funny spot, and bodes well for the upcoming Windows Server 2008 marketing push.

Link: Lone Server