Meantime, here’s a Web/TV merger that does make sense: NBC late-night host Jimmy Fallon,watching his own show on tape while commenting on it, live, on the Web.

Really, it does make sense: Like all late-night shows, Fallon’s is recorded in the afternoon, the day of broadcast. But next week, each night the show airs, Fallon will go live on the Web at 12:30 Eastern and provide a running commentary on the show, DVD-style. Fans will also be able to chat and interact with him, via video powered by UStream.

Pretty clever convergence, no?

Aside: Fallon’s show has always been a deliberately Web-friendly one. Fallon is a fairly famous Twitterer, which has caused some problems in the past, and the show goes out of its way to book tech-savvy guests like the Digg dudes.

And it’s also good about offering Internet-only goodies like this clip–an off-air encounter between Fallon and guest Jerry Seinfeld from last night’s show.

Remember those Microsoft ads starring Bill Gates and Jerry Seinfeld? The ones that confused and upset the blognoscenti and vanished from TV after just a brief stint in 2008?

All part of the plan, Microsoft says now. David Webster, chief strategy officer for Redmond’s central marketing group, tells TechFlash that the ads were supposed to be confusing. So you’d pay more attention to them, and to the next several campaigns Microsoft had loaded up.

“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,” he 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.”

This actually sounds like a plausible explanation to me. And I seem to be in the minority of people who actively liked the ads. Still, Webster and his co-workers certainly seem to have had their feelings hurt by the public raspberries the ads generated. Check out the defensive tone here:

But you know, it is what it is, and they will live forever in Internet posterity as being either something that people treat as a cult classic, or as a random curiosity. But I still get mail from people saying, “Hey, could you guys do that as a sitcom? I’d love it as a web series, I think they had great chemistry, I’d like to see them do it in the future.” Like anything, things become cult classics for some people for some reason, and there’s a core group of people who really wanted to see us go further with those.

It’s also interesting that many of the original clips of the ad have disappeared from YouTube, though you can still find a few that give you a good sense of what Microsoft was trying to. Go ahead and refresh your memory:

And if you’re a Verizon (VZ) Fios TV subscriber and you pay for HBO, you’ll get access to it for free starting tomorrow. But if you don’t want to wait–and you’re both a Comcast (CMCSA) and HBO subscriber–you can go to Comcast’s Fancast.com and watch the same programming there. It’s all the same stuff.

So to be clear: HBO Go isn’t really a new service. It’s a new site and player*, which perches on top of the same “TV Everywhere” strategy parent company Time Warner (TWX) has been pushing for a year or so. Which you can boil down to: If you pay the cable guys to watch it on TV, they’ll let you watch it online, too.

You can debate the merits of this strategy and whether the programming guys would be better off selling their stuff directly to consumers and skipping the cable middlemen altogether all you want. But the cable-first strategy isn’t going to change anytime soon.

HBO’s aim is to be both “consumer friendly” and “affiliate friendly,” HBO co-president Eric Kessler explained today. Translation: The company wants to make sure it gets paid by the cable guys, who get paid by you and me.

But couldn’t there be some fee I could pay HBO to just go directly to the Web, even at a premium of the price for a regular TV subscription? Nope, says Kessler, who then repeats something you often hear from the cable TV industry:

“The scale of the audience that wants to watch HBO that isn’t buying television, it’s a very small audience.”

Meanwhile, HBO Go points out the difficulty would-be online competitors like Netflix (NFLX) and Apple (AAPL) et al will have providing consumers with what they want when they want it: A lot of the digital rights to the stuff they want are already locked up by the likes of HBO during various “windows.”

One other point: Networks like HBO and cable providers like Comcast both want to be the viewers’ gateway to online video, for obvious reasons. But viewers won’t care whether they’re watching “Curb Your Enthusiasm” on HBO’s site or via Fancast; they just want to watch that episode where Marty Funkhouser tells Jerry Seinfeld a really dirty joke.

So someone–it could be the cable guys themselves or a start-up like Clicker–needs to build a comprehensive TV Guide for the Web. And then hope that they’re right about all those people who are happy to keep paying for TV.

*Because you now need to ask this with every consumer tech rollout: No, HBO Go won’t work on the iPad. Because the site’s player is built with Adobe’s (ADBE) Flash, and Apple wants nothing to do with Flash.

Here’s a new one that splits the difference: It features Patrick Warburton, best known as “Puddy” on “Seinfeld”*. A good chunk of Apple’s target audience will get a kick out of seeing a tertiary character from an iconic sitcom. And the chunk that doesn’t know or care about “Seinfeld” will be the none the wiser. Clever!

The really clever part, of course, is Apple getting the likes of me to distribute its advertising, gratis.

Oh. Speaking of those Jeff Goldblum ads, this is an old meme but I find it entertaining anyway: Someone went ahead and took all of his old Mac spots and slowed them down to half-speed. Which gives you an impression of what Jeff Goldblum might be like if he was rambling on about Apple (AAPL) products at the end of a very long night of drinking. There’s a whole set here, but this should give you a taste:

*Jerry Seinfeld himself, of course, became a Microsoft (MSFT) pitchman for a brief, largely unsuccessful  stint last year. But if you want to see him on TV this fall, check out the new season of HBO’s “Curb Your Enthusiam,” where he’ll be appearing with all of his old cast-mates.

“PC unit growth was stronger than we expected in all markets but Eastern Europe in the first quarter of 2009. In particular, consumer shipments were much stronger than we anticipated,” said Gartner’s George Shiffler. “However, professional shipments continued to struggle, and we think much of the growth in consumer units was due to vendors and the channel restocking inventories rather than an upsurge in demand.”

Well, hopefully that will all change after the October launch of Windows 7, right?

Nope. Not according to Gartner (IT), anyway. Unless Microsoft (MSFT) is planning another $300 million ad campaign featuring Jerry Seinfeld.

“Unless Microsoft mounts a major marketing campaign in support of Windows 7, we think consumers will simply adopt the new operating system as they would normally buy new PCs and/or replace old ones,” Shiffler said. “As for professional users, we still expect them to put off adopting the new OS for at least a year until they have fully tested their applications against it.”

“PC unit growth was stronger than we expected in all markets but Eastern Europe in the first quarter of 2009. In particular, consumer shipments were much stronger than we anticipated,” said Gartner’s George Shiffler. “However, professional shipments continued to struggle, and we think much of the growth in consumer units was due to vendors and the channel restocking inventories rather than an upsurge in demand.”

Well, hopefully that will all change after the October launch of Windows 7, right?

Nope. Not according to Gartner (IT), anyway. Unless Microsoft (MSFT) is planning another $300 million ad campaign featuring Jerry Seinfeld.

“Unless Microsoft mounts a major marketing campaign in support of Windows 7, we think consumers will simply adopt the new operating system as they would normally buy new PCs and/or replace old ones,” Shiffler said. “As for professional users, we still expect them to put off adopting the new OS for at least a year until they have fully tested their applications against it.”

Here are 11 ads the company has commissioned to promote its Chrome browser. Most are designed to be “viral videos,” though you might see one of them–”Evolution of Simple”–on TV because Google (GOOG) will be buying some airtime for the spot using its TV Ads platform.

So really, it’s a twofer–an ad for both the browser and for Google’s attempt to break into television advertising, which hasn’t gotten very far to date.

Andrew LaVallee at Digits, a section of The Wall Street Journal, has more about the campaign, and you can download the browser here. Unless you’re using an Apple (AAPL) computer, since Chrome doesn’t work (yet) on Macs.

I’m not a huge fan of any of these, but what do I know? I liked those Microsoft (MSFT) ads with Jerry Seinfeld that inspired much braying from the Web’s amateur ad critics.

Though I do sort of like the “Google Chrome” spot, with that Beatles/ELO soundtrack that turns out to be the work of someone named Tim Myers. The song has also been used to sell Lay’s potato chips in a cool/creepy Canadian commercial; it also showed up on an episode of ABC’s “Ugly Betty.”

If you ask me, it sounds like something you would hear in an Apple ad.

With a new administration coming into power, it makes a lot of sense for Microsoft to launch its new “Microsoft on the Issues” blog this week.

Covering legal and policy issues, the opening post by Microsoft (MSFT) General Counsel Brad Smith noted:

Today we are launching ‘Microsoft on the Issues’ to open another, more direct line of communication that will enable us to quickly and succinctly provide our perspective on the pressing technology matters of the day. We do not want this to be a one-way conversation. We want to create a transparent dialogue with readers and stakeholders. We want to enhance our participation in discussions that propel policy-making at local, national and international levels.”

But, so far, with only two posts and few comments, it’s a tad dry–and, by that, I actually mean dull–and in desperate need of some spicy sauce to jazz up the joint.

Here are some modest BoomTown suggestions:

Never seen before behind-the-scenes photos of Microsoft honcho Bill Gates cracking wise with the legal team during the software giant’s antitrust trial in the late 1990s!

CEO Steve Ballmer’s personal ruminations in a “BOMB-er” blog on the dangers of Google (GOOG) dominance over search–the uncensored version!

A legal argument about how Yahoo (YHOO) CEO Jerry Yang should be declared incompetent for not taking Microsoft’s very, very, very generous offer. (Title: “Is It Something We Said?”)

Microsoft’s collection of the outtakes from the Jerry Seinfeld commercials, with a very special essay about the Constitutional right to be extremely weird.

No?

I guess, as Smith wrote, it will be a “wide range of issues, from broadband access, online privacy and data portability to intellectual property protection, competition law, international trade and immigration.”

Also, he promises to write about the “next wave in the computing revolution and its potential to use the power of software and the Internet in new ways to enhance choice for consumers, businesses and governments.”

Thus, the first post–on workforce development and skills training by Global Corporate Affairs VP Pamela Passman.

In any case, I am still waiting for that Ballmer blog.

First, Microsoft tried ads starring Jerry Seinfeld and Bill Gates. Next it tried ads starring anonymous Windows fans.

Now, the next step? Why advertising starring anonymous Windows fans–created by anonymous Windows fans–of course.

MediaMemo likes the new batch, which are cobbled together from video clips that Windows users uploaded themselves.

But then again, MediaMemo has liked all of the ads that hotshot agency Crispin Porter + Bogusky has created for Microsoft (MSFT), and thinks that all of the blogosphere carping and cheering about the ads is a bit silly.

It’s also exactly what Crispin wanted us to do in the first place.

Anyway, see for yourself–and tell me what you think in the comments section (you’ll need to register to do so).

Full-length version:

Mini version:

G.ho.st, which stands for “Global Hosted Operating System,” is claiming it has a pending trademark registration for the tagline “no walls.”

G.ho.st has used the phrase for almost 18 months and is alleging that it pertains specifically to operating systems (as shown in the screenshot here).

In a letter sent earlier this week to Microsoft CEO Steve Ballmer and many others, which BoomTown has obtained, G.ho.st CEO Zvi Schreiber claims that the software giant has violated G.ho.st’s pending trademark for the ad phrase “no walls” and asks Microsoft (MSFT) to remove it from the company’s marketing materials.

Microsoft’s advertising campaign, which launched this month and had a rocky start with poorly received commercials featuring comedian Jerry Seinfeld and Microsoft Founder Bill Gates, uses the taglines “Imagine No Walls” and “Life Without Walls” to tout its Vista operating system. (See a screenshot of one example below; click on it to make it larger.)

G.ho.st, which is hosted by Amazon (AMZN), is yet another of many attempts to make cloud computing real and is competing to grab customers from the software-based Windows powerhouse.

A Microsoft spokesman, in an email to me, dismissed G.ho.st’s claims.

He said:

“We are aware of their concerns and believe their claims have no merit. We are not aware that Ghost has any trademark registrations or other rights that would be infringed by our ‘Life Without Walls’ campaign. To our knowledge, the right they have asserted, namely, a U.S. ‘registered trademark application,’ in the phrase ‘No Walls,’ does not exist.

“To our knowledge, Ghost has no trademark registrations or other rights in the phrase ‘No Walls.’ Even if they did, they cannot prevent others from using the words ‘no walls’ together in a sentence or in a descriptive manner in ad copy. Nor can they claim ownership in word ‘wall’ or the idea of a wall. The tagline for Microsoft’s new ad campaign is ‘Life Without Walls’–a slogan that, taken in its entirety, is not confusingly similar to Ghost’s purported ‘motto.’”

G.ho.st launched at our D: All Things Digital conference this past May (where Ballmer and Gates also appeared).

Here are two videos showing the start-up’s whole demo:

And here’s G.ho.st CEO Zvi Schreiber’s full email letter to Ballmer (with email addresses and other personal information redacted):

From: “Zvi Schreiber (G.ho.st)”
To: [Steve Ballmer]
Cc: [redacted]
Sent: Wednesday, September 24, 2008 12:15:41 AM (GMT+0200) Auto-Detected
Subject: G.ho.st Virtual Computer NO WALLS trademark

Here are videos of three of the new “I’m a PC” ads from Microsoft’s next phase of its Vista-doesn’t-bite advertising campaign.

You can decide if you like them or not. But BoomTown is declaring them a vast improvement on the quirky initial commercials that featured Microsoft Founder Bill Gates and comedian Jerry Seinfeld.

Microsoft has insisted that those three ads, which attracted a chorus of critics, were just a “teaser” to this second phase of a $300 million ad campaign, in which the software giant seems to be returning from its short visit in hipville to a more normal marketing message.

And these new Microsoft (MSFT) ads are definitely normal and more clear, having an it’s-a-small-world-after-all panoply of people declare that they are all PCs.

The message is aimed at attacking the more elitist message of Apple (AAPL) ads, which have effectively mocked PC guy relentlessly over the years as an oaf.

In Microsoft’s ads, its own PC guy complains at the start of each that “I’ve been made into a stereotype.”

The ads proceed to show regular folk with some celebrities mixed in (including Gates, TV hottie Eva Longoria and feel-good author Deepak Chopra), all proudly declaring their PC affiliation.

While the ads feel like they are tapping a little too much into that uneasy red-state-blue-state vibe–as if we need more of that–they’re also nicely done, thankfully, although not particularly new or innovative.

Which, after the Gates/Seinfeld oddity, is a good thing.

Here are three of the new ads (click them all at once for an even better experience!):

While the very quirky ads recently rolled out by Microsoft to tout itself–starring Microsoft Founder Bill Gates and comedian Jerry Seinfeld–got a ton of hype, it turns out there will be no more than than the three already released for now.

It seems the churros have gone cold.

According to a Microsoft (MSFT) spokesman, the Seinfeld advertisements were apparently just a warmup for more to come tomorrow, though the new ones will not use Seinfeld in any significant way.

But they might still feature Gates and Seinfeld could return.

But the main Seinfeld/Gates pairing was, said Microsoft, just a “teaser” for the next phase of the $300 million campaign to tout its beleaguered Windows Vista operating system.

[UPDATE] Said Microsoft in an official statement: “We will be executing the second phase of our advertising campaign tomorrow, as planned from the start.”

The company said upcoming personalities in the new ads will include feel-good author Deepak Chopra, television star Eva Longoria and musician Pharrell Williams, and they will also use Microsoft’s own version of the dumpy PC guy character to attack Apple’s hugely successful Mac/PC ads.

BoomTown is dubious, to say the least, that Microsoft can be more clever than Apple (AAPL) in the marketing arena. And by dubious, I mean its chances are as good as Lehman Bros. rising from its financial grave.

News of the development was first reported by Valleywag, which said in its post title that the ads were canceled, which is untrue.

But Microsoft’s rep stresses that this was the plan all along, to jump-start the marketing conversation, even though the ads have, in fact, not gotten a lot of praise.

You be the judge. Here are the three ads. The first with the churros joke and the second and third visit with a family, combined:

First off, as Digital Daily’s John Paczkowski pointed out to me today, you have to give Yahoo props for using Gogol Bordello as the soundtrack and–more to the point–actually knowing about Gogol Bordello in the first place.

“Since when does [Yahoo CEO Jerry] Yang listen to gypsy punk?” asked Paczkowski in an email to me today.

Since Bill Gates started eating churros with Jerry Seinfeld and adjusting his skivvies hands-free, that’s when!

Oh dear, Yahoo (YHOO) has succumbed to the hipster, ironic thing–an unfortunate marketing virus that has hit Microsoft (MSFT) of late too–in an under-the-covers “Start Wearing Purple” online marketing campaign.

The Internet company is now out with a Web site touting itself, advocating that people “celebrate purple.”

Purple and yellow have always been Yahoo’s colors–even while Google (GOOG) just up-and-grabbed the whole spectrum and emerged victorious.

Nonetheless, Yahoo is going to town on the purple idea, using a lot of its tools and products in the process to show itself off.

The effort starts with a video of multiracial hipsters doing wacky stuff, including a yodeling Yang (see at top), which makes it look like a very alternative version of “High School Musical.”

Also on the site: See purple-inspired photos from Flickr; view videos of “Purple Pranks” (first up, of course, ringers singing the purple song in an elevator to unsuspecting folks); peruse profiles of “Purple Picks” (like the cool crafts site Etsy and artist Clarence Lee) and “Purple Pioneers” (a mix of do-gooders and more hipsters, so far); and even search the word “purple” on Yahoo to fun-filled results.

There’s also a bunch of purple bikes apparently traveling the globe and taking pictures that will be uploaded to a Flickr map. And, natch, you can buy purple clothes.

After trolling the site for a bit, I can tell you I live in the dead center of San Francisco’s Castro neighborhood and we don’t get that purple here ever!

In other words, it’s all very high-concept, much like the dancing guy video that Yahoo did recently (see that very sweet morale-building video at the very bottom).

But to really resonate with the mass of users Yahoo needs to hold onto, as dull as this sounds, I would just like a simple explanation of why I should use Yahoo in my daily life.

The legendary Apple (AAPL) Mac-PC ads that Yahoo and Microsoft are clearly trying to mimic are good primarily because they have a message in each funny exchange about why you need to own a Mac.

Not so much with this quirky Yahoo effort, which is laudable, but a waste of time.

In the main “celebrate purple” video on the site, part of the tag line is: “Deep inside everyone is a Yahoo! waiting to come out. Set yourself free with a little purple.”

Actually, deep inside Yahoo is a Yahoo waiting to come out. And it is going to take more than purple to coax that magical creature out into the light again.

Like the first ad in the campaign, “Shoe Circus,” this spot clearly isn’t intended to pitch anything. It’s meant to redeem and recondition Microsoft’s public image, which has been turned into a joke by Apple’s (AAPL) persistent and devastating mockery. Consider Cupertino’s latest “Get a Mac” ad in which John Hodgeman’s PC character presents a faux editorial, “Stop Switching to Mac!,” on Time.com, NYTimes.com and elsewhere.

How do you respond to something like that?

Perhaps by showing folks that you’re a market leader that’s not quite as stodgy as they’ve been lead to believe. “Just as somebody might tell a joke to lighten up a room or get somebody’s attention before changing gears, these first ads were designed to tap people on the shoulder and say, ‘Excuse me. We’re back and we’d love a few moments of your time,’ Windows Director Chris Flores explains. “Will seeing Bill and Jerry enjoy each other’s company make people run out and buy a new laptop? Or correct misperceptions some non-users might have about Windows Vista? Certainly not. We’d be crazy to think they would. That’s why we’re continuing the Mojave Experiment ads. That’s their job. And they do their job simply by giving people who’ve never done so an excuse to check out Windows Vista for themselves. But this campaign, when fully unveiled, will talk about Windows in all its forms. Not just the OS for PCs we happen to be shipping today. In fact, not just an OS. And not just on PCs. Simply put, this campaign isn’t about Windows Vista. It’s about Windows. That might not be what some folks were/are expecting. And it might be hard to believe given what you’ve seen so far. But remember, we have gone on record saying the broader campaign will ‘tell the Windows story’ and we intend to judge its success on that basis. In that light I think it’s pretty safe to conclude we don’t expect the little logo at the end of these spots to do all that work by itself.”

From: Bill Veghte
Sent: Thursday, September 04, 2008 5:37 PM
To: Microsoft – All Employees
Subject: Telling the story of Windows

This first set of ads features Bill Gates and comedian Jerry Seinfeld. Think of these ads as an icebreaker to reintroduce Microsoft to viewers in a consumer context. Later this month, as the campaign moves into its next phase, we’ll go much deeper in telling the Windows story and celebrating what it can do for consumers at work, at play and on-the-go. At that time, I’ll be back to share more information about our plans to further strengthen the bond between consumers and Windows–one of the most amazing products, businesses and brands of all time, and, with the right tenacity, passion and agility from all of us, a story that has many great chapters to come.

From: Bill Veghte
Sent: Thursday, September 04, 2008 5:37 PM
To: Microsoft – All Employees
Subject: Telling the story of Windows

This first set of ads features Bill Gates and comedian Jerry Seinfeld. Think of these ads as an icebreaker to reintroduce Microsoft to viewers in a consumer context. Later this month, as the campaign moves into its next phase, we’ll go much deeper in telling the Windows story and celebrating what it can do for consumers at work, at play and on-the-go. At that time, I’ll be back to share more information about our plans to further strengthen the bond between consumers and Windows–one of the most amazing products, businesses and brands of all time, and, with the right tenacity, passion and agility from all of us, a story that has many great chapters to come.

There will be a lot of different reactions to the first of Microsoft’s newest series of commercials, featuring Founder Bill Gates playing straight man to comic Jerry Seinfeld.

Set up as a discount shoe-buying skit, Seinfeld helps Gates purchase a pair called “The Conquistador,” and for some Seinfeldesque reason, it’s churros all around.

Actually, it feels a lot like the frequent and excellent Microsoft internal spoof videos Gates does with various celebs.

I have always liked them a lot and I like this one too, as it is quirkily charming (or is it charmingly quirky?).

But I am not sure the Gates-Seinfeld kibitzing will really get a lot of people talking about Microsoft (MSFT) products, as is the marketing goal.

And they surely are no where near as spot-on as Apple’s famed PC-Mac guys commercials, which are memorable and witty and deliver the message that Apple (AAPL) products are better.

What might be more effective, of course, at least in the Internet arena, is for Microsoft to get off the stick and lay out its next Web strategy clearly, especially in the wake of its failed attempt to acquire Yahoo (YHOO), and name the digital chief it said it planned to.

Several sources with knowledge of the situation expect an internal choice to helm the part of the business that was run by former Microsoft exec Kevin Johnson, who left after the software giant’s bid for Yahoo failed.

Although an external star coming in would be CEO Steve Ballmer’s top choice, I would guess, top internal contenders are Brian McAndrews, who came to the company via its $6 billion aQuantive acquisition, and longtime exec Yusuf Mehdi, who was Johnson’s strategy guy.

(BoomTown votes for a combination of both to make it extra complex!)

In any case, if it is serious about taking on rival Google (GOOG) in the online ad space and becoming at least the No. 2 player in the market, Microsoft has to move sooner than later and definitely much faster and it has a lot of options.

With Yahoo’s stock circling the drain, closing yesterday at $17.75, will Microsoft think about another bid for even a part of the Internet company?

Or will it try, as it claims, to get truly serious about building its business organically with programs like Live Search cashback, a deeper focus on vertical search improvements in places like video, images and mapping, and more content on its MSN sites?

Or should it be aggressively looking around for other properties to purchase to bolster its Web assets, such as the company that owns the Ciao price comparison and online shopping sites in Europe, for which it just forked over $500 million?

Of course, Microsoft will likely keep trying all of these, although I hope not in the muddling way it has behaved for far too long.

Johnson was entirely right in his internally controversial concept that being one of the top players on the Web is key to Microsoft’s future, even more than its lucrative Windows software hegemony.

(If you want to read an interesting take as to why, don’t miss New York Times columnist Joe Nocera’s “Does Windows Still Matter?” post yesterday).

And with Google’s new foray into the browser business this week, Microsoft surely has to be certain that it does not lose in the one place it does dominate.

In other words, Microsoft has a lot of work ahead of it, well beyond amusing us with Gates doing a thankfully hands-free adjustment of his boxer shorts.

In any case, you should see that, so here’s the first Gates-Seinfeld commercial:

The success of Windows is our number one job. With SP1 and the work we’ve done with PC manufacturers and our software ecosystem, we’ve addressed device and application compatibility issues in Windows Vista. Now it’s time to tell our story. In the weeks ahead, we’ll launch a campaign to address any lingering doubts our customers may have about Windows Vista. And later this year, you’ll see a more comprehensive effort to redefine the meaning and value of Windows for our customers.”

– Microsoft CEO Steve Ballmer, July 23, 2008

So Microsoft’s widely publicized “edgy” ad campaign, the one designed to counter the Apple (AAPL) ads that have so eroded its brand, is to feature Jerry Seinfeld as celebrity pitchman. And in many ways that does more to illustrate the sad differences between the two companies than the “Mac vs. PC” ads it’s designed to combat. Because Microsoft (MSFT) has chosen as quarterback for this campaign a tired ’90s sitcom star who not only used a Mac in the series that made him famous, but closed out Apple’s 1997 “Crazy Ones” ad–which, ironically, aired only once, during the series finale of “Seinfeld.”

So Microsoft, in an effort to overhaul its image and upstage the cool kids down in Cupertino, seems to have done little but confirm the message of its rival’s ads: “I’m a Mac, You’re a Dork,” or, in this case, a dated comedian. Really, the company might as well have hired Don Rickles for the job. Certainly, he would have come cheaper than the $10 million Seinfeld is rumored to have demanded. And there’s life left yet in that “What are you lookin’ at, you hockey puck?!” line of his.

Anyway, in the end, it’s not marketing that’s the issue here. It’s the product.

The success of Windows is our number one job. With SP1 and the work we’ve done with PC manufacturers and our software ecosystem, we’ve addressed device and application compatibility issues in Windows Vista. Now it’s time to tell our story. In the weeks ahead, we’ll launch a campaign to address any lingering doubts our customers may have about Windows Vista. And later this year, you’ll see a more comprehensive effort to redefine the meaning and value of Windows for our customers.”

– Microsoft CEO Steve Ballmer, July 23, 2008

So Microsoft’s widely publicized “edgy” ad campaign, the one designed to counter the Apple (AAPL) ads that have so eroded its brand, is to feature Jerry Seinfeld as celebrity pitchman. And in many ways that does more to illustrate the sad differences between the two companies than the “Mac vs. PC” ads it’s designed to combat. Because Microsoft (MSFT) has chosen as quarterback for this campaign a tired ’90s sitcom star who not only used a Mac in the series that made him famous, but closed out Apple’s 1997 “Crazy Ones” ad–which, ironically, aired only once, during the series finale of “Seinfeld.”

So Microsoft, in an effort to overhaul its image and upstage the cool kids down in Cupertino, seems to have done little but confirm the message of its rival’s ads: “I’m a Mac, You’re a Dork,” or, in this case, a dated comedian. Really, the company might as well have hired Don Rickles for the job. Certainly, he would have come cheaper than the $10 million Seinfeld is rumored to have demanded. And there’s life left yet in that “What are you lookin’ at, you hockey puck?!” line of his.

Anyway, in the end, it’s not marketing that’s the issue here. It’s the product.