[raw_anon_1111]

Because with iTunes, I could and did have regular playlists and smart playlists using conditions like ratings, last played, play count, number of times skipped (so that it would automatically be removed from a playlist if I continued to skip a song on my iPod or computer), genre, year released, etc.

You couldn’t have that metadata with just file syncing. Later when iTunes was introduced, it had to support DRM.

Later it also had podcast syncing.

I used iTunes to burn CDs before I had an iPod.

And don’t forget that Jobs being able to negotiate users being able to buy music on iTunes with DRM [1] and letting users burn them to a DRM free CD was so revolutionary that even Bill Gates was impressed.

https://9to5mac.com/2021/07/09/unearthed-email-shows-bill-ga...

[1] later Jobs argued in the same “Thoughts on Music” letter that instead of Apple licensing its DRM the record label should license DRM free music to everyone since most music was already sold as DRM free CDs and then everyone’s music could work anywhere. Only one record label took them up on the offer from day one. It wasn’t until 2009 that all of the record labels agreed.