I know you've been dealing with this for two years. However, none of the recommended solutions works for me. iTunes will play one song, and stop. Or, it will play one song – over and over and over. I am using iTunes vsn. 12.0.1, updated on 10/21/14, on a Mac running OS 10.7.5.
Can’t play albums in iTunes
itunes
Related Solutions
iTunes defines the random order of the tracks when you first specify set "Shuffle". (This is so that the skip forward / backward buttons work in a reasonable manner.) If you never turn Shuffle on or off, that order is never changed. Just disable and then re-enable Shuffle to get a new random order of tracks.
For more detail, see Why isn't iTunes shuffle random?.
As of iTunes 10 (or possibly 9), the main library window has the option to do exactly what you want. You need to have it in Album List mode (View menu -> as Album list; or the 2nd option in the view controller:
Then select the "Album by ..." pulldown and select Album by Artist/Year:
You should be all set and have a nice organized list of albums sorted by artist and year.
Best Answer
This is often caused by iTunes' insistence on only playing songs that are 'checked', even though you can't tell whether they're checked or not except in Songs view.
If you don't need the functionality that checking songs is used for (syncing with other devices, or limiting what appears in smart playlists), you can turn it off by unchecking Preferences > General > Show List Checkboxes. Then iTunes will play any selection you like without stopping.
If you don't want to disable checkboxes, as @Buscar웃 says, the Up Next list is your (somewhat unintuitive) friend.