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Apple and Matt Groening go way, way, way back...

http://comicsalliance.com/matt-groening-apple-macintosh-broc...

Well, it's exposure for said brands anyway (and being tied to Macs, too), so it's probably a good deal from an advertising standpoint (even more if Apple is paying them for it.)

The Simpsons are always jokingly referring to Apple. They have the apple logo with two bits out of it. I'm sure The Simpsons are happy to tie their name like this.

You probably meant 'the Simpsons' instead of your first Apple?

I don't think the portrayal of Apple in the Simpsons is very positive though, it's often shown as cultish.

There's Chi from Chi's Sweet Home on one of them. I wonder if they actually got the rights for that or just figured the Japanese rightsowners (probably the original manga author) wouldn't care.

It's questionable as to whether copyright law covers the drawing of a cat in a photograph of a laptop with a picture of the cat stuck to it.

If the rightsholders do care, nobody tell them about Pixiv.