I would ditch those three and consider replacing them with:
* Johnny Cash - At Folsom Prison
* Michael Jackson - Thriller
* Wu Tang Clan - Enter The Wu Tang
Some punk and metal representation would be good too. And, honestly, Play hasn't held up well over the years. If you want something more representative or influential, maybe Orbital's brown album or Underworld's dubnobywithmyheadman.
Though I thought it was actually a pretty well-curated set of albums. "Best" isn't always the... well, best, thing to aim for in a collection.
This was the assumption through the later half of the 20th century, but I don't think it's the case at this point. I haven't even heard The Beatles in a commercial context in about a decade (something unthinkable as early as 2000). Hip hop clearly had a large influence on the pop culture of today and (totally unrepresented in this collection). Plus there's really no excuse for including The Dave Matthews Band :P
Just for reference, these are the top 100 songs of 2000. The year before the iPod was introduced.
None of the hip hop songs that were popular were groundbreaking - mostly just bubble gum rap. I doubt very seriously that Apple would have been willing to put any socially conscious rap on iPods.
This is to be expected of course, I just think it's humorous.
You can be on the cutting edge of music without liking hip hop or electronic music. The problems wasn't the genres he picked, but the incredibly generic band choices within those genres.
I do like hip hop (and electronic is slowly growing on me), but that doesn't mean that everyone that doesn't is out of touch. There's interesting music coming out of nearly every genre in 2019. That's the way it always is.
Not really, hip hop / rap was fairly mainstream by the late 1980s / early 1990s.