It's a strange conflict. So much of their other stuff is about togetherness mediated by technology (eg, facetime). And their Jobs-era presentations always ended with a note of appreciation for the folks who worked so hard to make the launch happen. But you're right that much of the brand imagery is solitary, right up to the whole "Here's to the crazy ones" vibe.
It's weirdly dystopian. I didn't realize it bothered me until moments before my comment, but now I can't get it out of my head.
"Here's to the crazy ones" is weirdly dystopian? :)
Think about the early ipod ads, just individuals dancing to music by themselves. https://www.youtube.com/watch?v=_dSgBsCVpqo
You can even go back to 1983 "Two kinds of people": a solitary man walks into an empty office, works by himself on the computer and then goes home for breakfast. https://youtu.be/4xmMYeFmc2Q