Today in Apple history: Apple fan Jerry Seinfeld joins the dark side


Microsoft ad
"What's the deal with bad advertising?"
Photo: Microsoft

August 21: Today in Apple history: Jerry Seinfeld appears in failed Microsoft ads 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’

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 “Get a Mac” ads, which humorously positioned Windows PCs as old fuddy-duddies next to the Mac.

Cupertino tried to pigeonhole Microsoft this way for years.

Jerry Seinfeld: Pop culture’s ultimate Apple fanboy

There was a certain irony in Microsoft trying to refresh its image by, once again, stealing directly from Apple’s playbook.

During the 1990s, legal battles over whether Windows ripped off Mac OS dominated the two companies’ relationship. Then, the early 2000s saw Microsoft debut the iPod-like Zune and, later, the Windows Phone.

Now it 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.)

A look at Jerry Seinfeld’s Macs over the years.
Photo: Seinfeld

Microsoft’s 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. The pair also talked about edible computers (seriously!).

“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 ads within weeks, and never mentioned them again.


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