August 21, 2008: Microsoft recruits comedian Jerry Seinfeld for a series of ads. It’s a naked attempt to shake the company’s reputation as a stodgy oldster (as opposed to Apple’s trendsetting hipster image).
Microsoft pays Seinfeld a reported $10 million for the ads. However, thanks to the Mac’s appearance in virtually every episode of Seinfeld over the years, the comedian remains the world’s most famous Apple fanboy.
Microsoft ad with Seinfeld is payback for ‘Get a Mac’
In 2008, Microsoft had a major problem: Apple had made Windows look desperately uncool with its “Get a Mac” ads. To turn things around, it recruited one of the most recognizable comedians on television — and, awkwardly, a longtime Mac user whose computers appeared throughout his hit sitcom.
The resulting ads were supposed to make Microsoft seem younger and more relatable, but their surreal humor landed with a thud, and the company pulled the campaign within weeks. The debacle was about more than bad advertising, though. It showed how convincingly Apple had won the culture war, turning Microsoft’s enormous market dominance into a liability when it came to something harder to buy: cultural relevance.
The Seinfeld ads were part of a $300 million Microsoft advertising campaign to overhaul the company’s image. They served as a direct response to Apple’s unforgettable “Get a Mac” ads, which humorously positioned Windows PCs as fuddy-duddies next to the Mac.
Those ads cast Justin Long as the laid-back “Mac” to John Hodgman’s hopelessly nerdy “PC.” Apple tried to pigeonhole Microsoft this way for years.
Jerry Seinfeld: Pop culture’s ultimate Apple fanboy
There was a certain irony in Microsoft hiring Jerry Seinfeld for the preposterous ads. The tech company once again tried to refresh its image by stealing directly from Apple’s playbook.
During the 1990s, legal battles over whether Windows ripped off the Mac’s operating system dominated the two companies’ relationship. Then, the early 2000s saw Microsoft debut the iPod-like Zune and, later, the Windows Phone. Both of those me-too products flopped.
In 2008, Microsoft pinned its hopes on Seinfeld, who displayed his beloved Macintosh collection in his fictitious apartment every week on his TV show in the 1990s. (By 2008, Seinfeld had been off the air for a decade.)
Photo: Seinfeld
Microsoft’s Jerry Seinfeld ads are a critical miss
A clever ad could have played with that idea in a subversive way, as if Microsoft somehow persuaded Seinfeld to jump ship. Instead, the campaign debuted with a badly received commercial in which Seinfeld helped ex-Microsoft CEO Bill Gates pick out shoes at a fictional store called Shoe Circus. The pair also talked about edible computers (seriously!).
A second Microsoft ad featuring Seinfeld and Gates made things worse. In it, they sat down for an awkward dinner with a stereotypical American family, making snide remarks about the food, before veering off into increasingly nonsensical territory.
In the third and final attempt at humor, Jerry gets framed for stealing a stuffed giraffe. Microsoft, and its ad agency, were clearly trying too hard.
Microsoft shows it’s out of touch
“The commercials were a train wreck from the beginning and only reinforced the idea that Microsoft is so far disconnected from regular consumers that it has no idea how to talk to them — even in an ad campaign,” ZDNet wrote at the time.
Daniel Lyons, who secretly blogged as Fake Steve Jobs, wrote that “hiring a TV star from the 1990s only added to the impression that Microsoft is stuck in a time warp, at a time when Apple is seen as the king of cool and is gaining market share.”
Microsoft pulled the Seinfeld ads within weeks, and never mentioned them again.
You can relive the glory by watching them below:
Watch the Microsoft ads with Jerry Seinfeld and Bill Gates
