When Jerry Seinfeld starts appearing in Microsoft Windows ads, will the fact that he always had a Mac on his desk during the iconic TV series figure into the work created by Miami ad agency Crispin Porter + Bogusky?

As reported by The Wall Street Journal today, Microsoft, frustrated that its Vista operating system becomes less and less attractive with each passing week, is turning to an ad strategy that will feature the uber-successful comedian Seinfeld, and even company founder Bill Gates.

It’s difficult, and unfair, to pass an opinion on ads I haven’t seen yet. But, going in, I’m suspicious of the strategy of using Seinfeld, 54, to attract new users and would-be Mac users to Vista and thus PCs.

One doesn’t have to look very hard to find the foil to this strategy. It’s the Apple campaign for Mac computers. Quick: name the two actors who play in the ongoing story in Mac ads in which the cool guy is the Mac and the older nerd, refugee from The Office” is the PC.? Certainly, a few readers of this blog can, but I’d say 99.9% of consumers can’t. [It’s Justin Long as Mac dude and John Hodgman as PC shlub). They do know, though, that those ads are for Mac and that they are entertaining. In fact, the Mac ads have a slight air of having been written by Seinfeld writers. They are that well done by TBWA/Chiat Day.

Using celebrities in lieu of a really good original idea is dodgy business. You know what brand of car Tiger Woods flogs? Buick. During the time that Woods has touted the GM brand, it has fallen bigtime in sales and popularity. Celine Dion was famously hired and then quickly cast aside by Chrysler after the automaker paid her about the same amount of money Microsoft is paying Seinfeld—$10 million. Gap dumped Sara Jessica Parker in 2004 when the actress was at her zenith, because the ads tested so badly. I’m struck by the irony that CP+B’s most successful work to date, for Burger King, has been grounded on original ideas and use of the iconic “Burger King,” not celebs.

One of the few exceptions I can recall, from my childhood, was Paul Masson being given a leg up by iconoclast actor/director Orson Welles, and the Miller Lite ads of the 1970s taking off by using professional athletes and coaches.

But make no mistake…Miller Lite was the star of those “Tastes Great. Less Filling Ads.” The ever changing casting of those TV commercials, pairing unique sports figures, was part of the fun and narrative.

Consider this assertion from a paper by Mohan K. Menon, University of South Alabama, Louis E. Boone, University of South Alabama and Hudson P. Rogers, Florida Gulf Coast University: “ Celebrity knowledge or expertise is defined as the perceived ability of the spokesperson to make valid assertions. The expert spokesperson seems most appropriate when advertising products and services that carry higher financial, performance, or physical risk while an ordinary consumer is considered best for low risk products or services (Atkin and Block, 1983). When celebrity spokespersons were viewed as experts in the product category, they were more liked (Buhr, Simpson, and Pryor 1987). Further, celebrity expertise tends to be highly correlated with believability and trustworthiness.”

Seinfeld’s advertising for American Express has been very successful. But consider that it doesn’t take any expertise to spend money on a credit card. Many people have caught on to the idea that you can pretty much do anything with a Visa card that you can do with an AmEx. Choosing between a PC and Mac is a much bigger deal for anyone. That decision is usually based on a combination of the consumer’s own usage experience and reading tech-advice articles, blogs etc.

Microsoft is specifically trying to get people to give Vista, which had initial glitches, to reconsider it. It is, in a way, a relaunch of Vista.

This from the WSJ article: “Microsoft's immediate goal is to reverse the negative public perception of Windows Vista, the latest version of the company's personal-computer operating system. Windows is Microsoft's largest generator of profit and revenue, accounting for 28% of the company's revenue of $60.4 billion in the year ended June 30. The software has sold well, and Microsoft retains an overwhelming share of the market for operating system software over Apple. But Apple's computer sales have been rising, and Vista is dogged by the notion that it has technical shortcomings and is hard to use. Apple's latest Mac vs. PC ads take swipes at Vista. Microsoft says early problems with Vista have been largely alleviated.”

And in my experience, re-launch is a word that should be stricken from the imaginary dictionary of marketing terms I keep in my desk.

Re-launch: To spend great sums of money on veterinary bills on a crazed horse that has already been severely injured while escaping from a burning barn. While the horse is being prepared to race another day, much money is also spent repairing the barn whose design will be changed again just when work is completed when a new chief stable director [CMO] is inevitably named.

Seinfeld, though it stopped producing shows in 1998, is the mother of all syndicated comedies. Today’s twentysomethings are just as apt to have seen every episode in re-runs as boomers and thirtysomethings are to have seen them in first-run. Too, Sony Corp.'s Sony Pictures Television, which distributes "Seinfeld"is about to send a 60-foot Seinfeld trailer around to campusus to promote re-runs.

And to think, the first college I attended had neither cable-Tv or the Internet.