Why can't iTunes resume playback of the last track I played before closing it?

If Safari can recall the last page I had open when I closed it, and Preview can open the last documents I had open, why can't iTunes resume playback of the last track I played?
Come on guys, a search on the internet will bring up discussions from the early 2000s with the question of resuming playback. Just add the feature already.

HI THanks for this helpful post. I will try this. I have 2 iPods. One is 3rd Gen. I love the little small square, so I bought it on ebay. Then I got a little iPod nano ( again a tiny square shape)
So I tried to sync them today and update them.
This is the response I got.
  I get a message that the original file cannot be found and asks if I want to try and locate file.  I locate the file and it's empty?!
This freaked me out because I have all this music I love. The only thumb drive is my back up drive which is not a thumb. Will the back up drive have my music files too?
Thanks-Peace Out

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