I’m not going to comment on Microsoft as a company, Bill and Jerry as people, or the ads as effective marketing, but I will say that I find the commercials entertaining so far. I appreciate them taking a risk.
Related quote from Seth Godin:
If you are willing to satisfy people with good enough, you can make just about everybody happy. If you delight people and create change that lasts, you’re going to offend those that hate change in all its forms. Your choice.
Entertaining? — Absolutely. Anything with Jerry Seinfeld is usually gold (at least when he’s not playing a bee). Bill Gates is also surprisingly funny and fresh.
Effective at reversing negative brand connotations about Windows? — Might be a good start, but they probably will have to branch out beyond just a few tv commercials. Bill Gates hasn’t been the face of evil since the whole browser wars shenanigans. Steve Balmer, everyone’s favorite sweaty maniac, still seems like the bad guy.