Using iTunes on the Mac... how can I automatically check the checkbox
next to each song title in the Library so that all songs are included
when I start playing them? (right now there are hundreds and hundreds
of songs unchecked, and I don't want to have to edit each one
manually). Thanks!

Hi chriso_312,

Checking or unchecking all the songs in your iTunes Library is easy! 
To do so, command-click on the checkbox next to an unchecked song. 
This should check all the songs, and command clicking on a checked box
will uncheck all your songs.

If this is unclear, don't hesitate to ask for a clarification.

Search strategy:
personal experience with iTunes

Regards,
Andy

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Clarification of Answer by andyt-ga on 05 Oct 2004 17:28 PDT

Sorry, just for clarification that would be apple-click I don't
believe it's called command-click.

Thank you -- this saved a ton of time going song by song!

Thanks for the rating and tip!

For iTunes Windows users the same can be accomplished using Ctrl +
Click on a checked item (to check all library) or Ctrl + Click on an
unchecked item (to uncheck all library).