I was reading Jim Rutenberg's story on this, and I was trying to work out why this new strategy by McCain rankles me. I think it's because the "Obama is Britney" line is too clever for its own good. The "John Kerry is an effete windsurfer" pitch made sense mostly because the country was at war. It directly attacked the idea that Kerry claim to the commander in chief mantle. The idea was that Kerry wasn't tough enough to deal with Al'Qaeda. Whatever you may think of that charge, it's clear and direct.
But the McCain attack is much more passive-aggressive, and isn't really as clear. First, I know that there is a substantial portion of Americans who don't like Britney Spears and Paris Hilton, but it's not clear to me that there is a significant portion of Americans who don't like celebrities in general. To the country, there is a large group of people who reliably drop millions of dollars to see the latest Will Smith feature. Implicit in the McCain attack is this idea that most celebrities are famous for being famous. I guess. But Tiger Woods is demonstrably a great golfer. Michael Jordan really did have a killer turn-around jumper. John Kennedy really did create the Peace Corps. Clint Eastwood really is a great actor and director.
In other words, it doesn't directly follow that celebrity equals bad president in the way that effete equals bad commander in chief. Being effete is considered the opposite of being a commander in chief. I'm not sure that being a celebrity is considered the opposite of being president. Indeed, it's kind of hard to be president and not be a celebrity--that comes with the job. So then what is the attack? Obama already is a celebrity--just like all our past presidents? Maybe I'm slow. I'm just not getting it.
The Beautiful Struggle: A Father, Two Sons, and an Unlikely Road to Manhood 
This Obama-is-a-celebrity line of attack is an extension of the Obama-is-presumptuous and Obama-is-elitist attack. But this time they add in young white women who have sex stories attached to them. Now it looks a lot like the GOP attack on Harold Ford to me. James Wolcott's comments are good: http://www.vanityfair.com/online/wolcott/2008/07/the-week-in-preview.html.
For me, the fact that a powerful 70 year old senator is using a 20 something year old addict as the punch line of his jokes, simply because she makes an easy target, rankles.
This was my issue with the McCain attack. America loves its celebrities. Famous for being famous, or famous for being talented, this is a culture that adores fame. McCain makes himself appear to be even more out of step with the country by using the celeb thing as a negative.
Of course, I laughed aloud at the Obama team response: 'Oops, He Did It Again," which just shows how much more deft and in touch they are.
Also, there is a hint of race-baiting by juxtaposing the negro with two young white women, but even that confuses, because people who don't like miscegenation are probably the same people who don't like Spears or Hilton. So, it's a fail there, too.
As a conservative and someone who likes McCain, I'm seriously disappointed to see him going down this road. You know who else was a celebrity? Ronald Reagan! I really *hate* the way they are responding to Obama. I have substantive disagreements with the man on a wide range of issues. But the allegation that he's an empty suit is ridiculous.
This convinces me more than ever that Obama is going to win big in November. The Republicans are doing the exact same thing Clinton did -- severely underestimating Obama.
Spears and especially Hilton have a vacuous and self-referential form of celebrity; they're mostly celebrities at this point *because* they're celebrities. A lot of people do get annoyed by that kind of fame, across a pretty broad range of the political spectrum, so it associates Obama with something negative, and it attempts to push the idea that Obama's celebrity status is a marker of triviality. Still, it seems like they're trying to pack a whole lot of unconvincing nuance into a not-very-well-put-together ad, so I doubt it will be directly effective.
Of course, it may still be indirectly effective, since it will form a wonderful jumping-off point for Bobbleheads who are always looking for another way to talk about nothing in a way that dismisses Obama as a candidate.
As an Obama Supporter, I'm much more worried about the accusations that his campaign is playing the "race card" at every turn. For the reasons you cite, I'm not too worried about the whole "Obama as an elite/celebrity" line. He can respond effectively to ridiculous ads involving Ms. Spears, but I think it's more difficult to respond to the race card accusations. (responding to it would require talking about race, which the media would compulsively feed on. The more the race card accusations are discussed, the more legitimized they become through mere repetition as an "issue")
This ad should have been mercilessly mocked for the pabulum that it is from the beginning. Instead, the talking heads and blogosphere are treating it to serious analysis and debate. The ad is media bait - and the media bit. It's just a very stupid, empty ad that doesn't even make any sense. Obama's a celebrity! Um, ok.
Can we move on now? And can we promise not to over-react to the next bucket of media chum the McCain campaign throws out there (Jenna Jameson, maybe)?
I think that the 'celebrity' angle is smarter than you're allowing. The problem McCain has is that a lot of people are excited by Obama, or see that their friends are excited by him. Obama is clearly the hip choice in this election. So how do you fight that without insulting the people who are excited? You say: "Of course you're excited, he's a celebrity, but that's not sufficient qualification to be president." It's not like anything else McCain has done is working.
@ Jim -
"'Of course you're excited, he's a celebrity, but that's not sufficient qualification to be president.'"
That's exactly my point. It doesn't make any sense. How many pretzel knots do you have to twist that logic into to wring some sense out of it? Let's talk it out: I'm really only a supporter of Obama's because he's a celebrity, like Britney and Paris. But the McCain campaign helpfully wrenches me from my confused state by pointing that out, so now I'm going to vote for McCain. Who is not a celebrity. Or something.
It also has the entire phenomenon backwards. Obama is a "celebrity" because of his supporters; he doesn't have supporters because he's a celebrity. The whole sorry thing is just plain stupid. Dumb as rocks from top to bottom.