Microsoft’s Jerry Seinfeld/Bill Gates Ads Explained: They Were Trying to Be Like LOST

In 2008, Microsoft subjected itself to a good dose of online and IRL heckling with its puzzling commercials featuring Jerry Seinfeld and Bill Gates, for which Seinfeld was reportedly paid $10 million. After three commercials, which were negatively (if unfairly) received, Microsoft promptly shelved the series, claiming that they were shifting to “the second phase of [their] advertising campaign … as planned from the start.” That next phase turned out to be the “I’m a PC” ads.

In an interview with a top Microsoft marketing strategist, TechFlash discovered that the confused reactions (though not their negativity) may have all been part of the plan: the aim of the commercials was to hook people in with their very obscurity, LOST-style.

TechFlash: (do read the full interview, it’s long but it’s worth it.)

“We figured that that sort of obscure nature of the communications would make people lean in a little more closely to see what we were going to next,” [Microsoft’s David Weber] says. “And that part certainly worked, in the sense that everybody leaned in, and they paid a lot more attention to our subsequent work than I think they might have had we just started with it.”

At that, Weber brought up the possibility that the ads might become a cult classic, and he may have a point; indeed, post-’90s, there’s been a lot of retro-fondness for Microsoft, or so it seems. At that, the Seinfeld/Gates commercials’ brand of cult classicism is probably not going to be discussed in the same breath as American Idol.

The first commercial, in which Gates and Seinfeld go shoe shopping together:

The second and third commercials, in which Gates and Seinfeld infiltrate a family:

(TechFlash via All Things D)