iTunes keeps track of the music you are playing in several ways: an easy one, which you may have already noticed, is that iTunes keeps a count of the number of times you have played a particular song, or track. (To view this information, simply switch to List View, right-click on the any of the column headers, and check "Plays" to display that column.) This tutorial explains how to get a listing of the recent songs and tracks you played in iTunes, from any the current computer.
Follow these steps to see which tracks you played last: (up to ten)
The limitation of this approach is obviously that iTunes only gives the last 10 songs recently played: the next section shows you how to see the last time you played any song from your iTunes library.
Here's how you can show your music in iTunes by date last played:
This is all you need to do to find out which songs were most recently played, and maybe rekindle with some older, forgotten albums and tracks! Once you are done, you can hide the Last Played column by right-clicking on it, and unchecking its name from the menu.