[Dain42]

Somewhere around 4.9 or 5.x is when I think it was best. They'd added library functionality for movies, TV, and audiobooks, which meant it was a one-stop shop for my media library on my Mac at the time. It was also still fairly lightweight, because it didn't have loads of stuff tacked on to it yet.

Really, the biggest thing I miss from iTunes, as a Google Play user, are the Smart Playlists. I loved being able to pull in every song I had from a set of artists and then shuffle through that. The "radio" features from Google just doesn't do it for me. I rarely want to listen to a bunch of music that's not in my library but which is similar to something I do have there. I'd much rather self-curate what I'm listening to. But I don't think the demand is there for that as much, now. I still wish they'd at least remove the 1000 song cap on playlists, so I could manually do this.