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Viewers actually started to side with Windows because of his lovable underdog persona. Attacking your competitor is a double-edge sword.
 
Funny in the beginning but it got old. With advertising you don't want to keep replaying the same old same old. People start tuning out.

They were good, but it was time to discontinue them.

Exactly.

At the beginning, the ads were smug.

After 6 months, they were smug and starting to get old. The series was no longer fresh.

That's when Apple and their marketing group decided to run the ads for another few years, until everyone, even people like my parents who don't care about computers, disliked the ads.
 
Apple stopped caring about computers as much. Perhaps they will come back as iOS vs Android when Apple hits #3 in smart phones in a few years.
 
That's why record sales of Macs continued unabated, right?

No, it's actually because the market for technology has been growing as a whole. Selling more than the previous fiscal year should be a habit, not a great feat for a tech company like Apple or Microsoft.
 
Viewers actually started to side with Windows because of his lovable underdog persona. Attacking your competitor is a double-edge sword.

To be honest those ads didn't improve my faith in Apple or what I think of them - I just found them entertaining. The PC character was good with his dry sense of humor too, although the Mac character was a bit sickly.

What I find good is when companies poke fun at themselves. Fox does that TONS on The Simpsons.
 
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