I don't think "Mac Nazi" jokes will do it. I'm a fan of Jerry Seinfeld, the comedian Microsoft has reportedly hired as a key pitchman in ads for Windows Vista. The campaign is designed to boost the image of its beleaguered operating system and answer Apple's wildly successful "Mac vs. PC" ads. (Those ads succeed partly because they poke Windows with gentle humor. The hip Apple guy even appears sympathetic to PC's plight.)
Sympathy and empathy don't come to mind when thinking of Seinfeld. He's known for hilarious satire and snide send-ups, like the infamous "Soup Nazi" who terrorized Jerry and his TV friends. If he wasn't funny, someone might call him arrogant and condescending, two adjectives that haunt Microsoft.
Microsoft already appears patronizing in its campaign. The company is showing how consumers tested an operating system called "Mojave" that was really Vista in disguise. Freed of their silly biases and unfounded apprehensions—and from having to get hardware and software to work with the new system—they love Vista.