I have to admit that I liked and enjoyed the – unfortunately, only – two Microsoft ads featuring Jerry Seinfeld and Bill Gates. In case you have not seen them, here they are…
and
For me, Microsoft has redeemed itself for all the bad things it has done in the past. That might sound a bit strong, but these ads are so good that I admire Microsoft for having the guts to run them. OK, it must have been so far beyond anything the usually confused participants in this game could understand that it was mostly rejected – and the ads have been pulled.
I think that the ads have nearly a Monty-Pythonishness and only a person well trained in Douglas-Adamishness can really appreciate them. This group is rather small, so it was drowned by the masses.
Compared to the Apple ads with John Hodgman as PC and Justin Long as Mac, the Microsoft ads are so totally senseless that they have broken reality – and I can’t help it, but I like surreal. They force you to look beyond the daily seriousness. OK, the Apple ads don’t appear serious, but they are; they are adversarial in nature by trying to put down the PC. (Funny side note: the PC character became more lovable and better known, publishing books and being interviewed by Xeni Jardin of Boing-Boing fame.)
Now let’s look at the MS ads – off-the-wall, surreal, and imaginative – and, I forgot, weird. What MS shows me here is that they could be just as unusual as Apple as a company, but that they have decided not to go this route because there were too few people to understand what they would have been doing. Instead, they went with what is real to most people – confusion!
So, by catering to the reality of this majority of the population, they managed to dominate the world with their software, and now they can come out of the closet – and they did.
Congratulations!

Good self parody, plus a touch of “We aren’t hip; in fact we are nerds, so there!”