How do I get iTunes to play the albums of an artist chronologically? I use iTunes all the time in the grid view, showing artists. If I click on one, all tracks of this artist are displayed, grouped by albums, sorted after the album name (alphabetically).

Now I click on the table header to sort for year instead and start playing one album.

After the last song of that album has played, the next album that will play is not the next one in the list, but the next one alphabetically.

Example:

Album A, 2003

Album B, 2010

Album C, 2005

When playing A, I want iTunes to play C next, then B. But it always will play B, even if I have it sorted after the year.
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.