So when the first ad featuring Jerry Seinfeld and Bill Gates aired, I was mildly confused and more than anything really wanted to give it a chance. But this evening Microsoft aired the second ad in the series and now I’m really just flat out baffled by Microsoft’s decisions with this ad campaign.

This particular ad has a full-length four and half minute version (below), and in keeping with the theme from the first ad, mere 5 seconds of the 270 available are used to mention anything about Microsoft or Windows.

Microsoft, bail out now before you confuse people even more.

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Tonight Microsoft aired its first ad featuring Jerry Seinfield. The ad (including Seinfield) is part of a new $300 million ad campaign Microsoft has put together to try and breathe new life in to the Windows operating system.

The 90 second ad spot is comprised mainly of shoe-banter between Bill Gates and Jerry Seinfield in a Shoe Carnival where Gates is a “platinum member.”

Interestingly enough, only 20 of the 90 seconds really have anything to do with Microsoft or Windows and of those 20 seconds, no time is spent actually touting much about Windows except that it is “The Future” and “Delicious.”

Microsoft has hinted that the new ad campaign is, in some part, a response to Apple’s successful “Get A Mac” campaign.

Personally, I’m not convinced this is starting on the right foot. My wife initially saw the commercial this evening and her response was basically “I don’t get it.” It’s one thing to try to be “hip”, but it’s another thing to try but completely fail at getting your message across. The attempt at humor is a nice change, though.

Check the new ad out below and let me know what you think. Is it effective or does its message get blurred?

Related research and analysis from GigaOM Pro:
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• Content Farms: The Players, The Benefits, The Risks
• What Google’s Honeycomb Means for Apple and Microsoft
• The Future of Work Platforms: An Overview