Microsoft announced it was moving away from its commercials featuring Bill Gates and Jerry Seinfeld just two weeks after unveiling the baffling teaser ads. Although the Seinfeld spots were so short-lived that they might be dubbed a failure—particularly since Seinfeld's deal with Microsoft is rumored to be worth $10 million—Microsoft and ad agency Crispin Porter claimed that the teasers did what they set out to do.

The tale of Gates and Seinfeld traipsing around with the common man wasn't the first ad campaign to struggle to find its audience. If Microsoft execs need a boost, they can console themselves that it could have been worse. They could have run one of these campaigns:

1. Virgin Blue Encourages Travelers to "Chuck a Sickie"

Earlier this year, budget Australian airline Virgin Blue ran a campaign telling potential passengers to "chuck a sickie" to take advantage of the carrier's ultra-thrifty fares. If you're unfamiliar with Australian slang like I was, you might think this campaign was some sort of horrifying effort to encourage the tossing of ill people. Instead, "chuck a sickie" is a more benign term for taking a sick day from work. Virgin Blue head Brett Godfrey didn't see the campaign as harmless fun, though; he didn't appreciate how they supported workplace absenteeism. Godfrey reportedly ordered the ads pulled just 29 minutes after seeing them for the first time.

2. Chevy Lets Users Generate Attack Ads

In 2006 Chevrolet ran a promotion tied to an episode of The Apprentice. The idea was that fans of the Chevy Tahoe could go on Chevy's website and "build their own" Tahoe ads from stock footage of the SUV rumbling through the wilderness. Chevy's website would host the ads, and the best ones would win concert and sporting event tickets for their directors.

However, the site drew more than a few directors seeking a soapbox from which to lambaste SUVs, often with hilarious results. The natural settings in the stock footage coupled with the directors' own trenchant barbs about environmental degradation fostered some truly biting attack ads that ran on Chevrolet's own servers. Here's an example:

3. Benetton Goes to Death Row

Italian clothing maker Benetton has never backed down from a controversial ad campaign; at various points the company has run pictures of terminal AIDS patients and a priest kissing a nun. However, many critics thought the designer finally crossed the line in 2000 with the campaign "We, On Death Row," which featured death-row inmates wearing their prison uniforms. The company's catalog contained pictures of 25 death-row prisoners, and their faces also appeared in print ads and on billboards around the world.

The campaign's creator, Benetton creative director Oliviero Toscani claimed that the images were simply used to draw attention to the brutality of the death penalty. Families of the prisoners' victims and victims'-rights groups contended the photos and accompanying narrative glorified the convicts and portrayed the killers as the actual victims. (The ads didn't mention the often-grisly crimes for which the subjects were imprisoned.) Public outrage grew so quickly that Sears terminated its contract to peddle Benetton's clothes, and the campaign could still be considered to be one of advertising's bigger blunders in poor taste.

4. Nike Dunks Its Sneaker Shots

Nike's Hyperdunk basketball shoes got a huge shot in the arm earlier this year when the viral video of Kobe Bryant wearing the sneakers and jumping over an Aston Martin became a web sensation. The print ads Wieden + Kennedy designed to go along with the shoes didn't fare quite so well. The ads presented large photographs of a basketball player being dunked on; the center of each shot was the hapless defender's face, which was obscured by the flying dunker's thighs and waist. Slogans like "That ain't right" appeared on top of the image. To basketball players, it seems apparent that the "that" in question is being on the receiving end of a ferocious dunk. Others, though, thought that the key to the image was one man's groin in another's face, and "That ain't right" was actually a homophobic slam. Following a heated debate on Wieden + Kennedy's blog and a loud public outcry, Nike scrapped the ads.

5. Just For Feet Trips at the Super Bowl

The Super Bowl is the biggest stage for advertising, and as such, it can be the scene for some of the industry's biggest failures. Few ads in history have failed quite so spectacularly as the one footwear chain Just for Feet ran during the 1999 Super Bowl. The spot portrayed a Humvee of white mercenaries chasing an African runner before giving him a cup of drugged water and then forcing a pair of Nikes on his feet while he's passed out. The ad weathered criticism for being colonialist, racist, and pro-drugging; the whole thing was offensive enough that no one seemed to even notice it didn't even really make sense.

Want more proof that the ad was transcendentally bad? Just For Feet sued its ad agency, Saatchi & Saatchi, for $10 million for convincing the company to run the ad despite its misgivings. Although Just for Feet eventually dropped the lawsuit, the company filed for bankruptcy protection later that year amid a serious accounting fraud.

Ethan Trex co-writes Straight Cash, Homey, the Internet's undisputed top source for pictures of people in Ryan Leaf jerseys.

See also...

Shedding Light on Trade Secrets

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Why is the Drinking Age 21?

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7 Companies that Fired Their Spokesmen

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6 Cases of Shamelessly False Advertising

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Advertising Icons: Where are they now, and who were they then?