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This seems like a common complaint for which I've found no satisfactory answer elsewhere on the Internet:

I want to join two or more existing tracks in iTunes so that they play as one and are thus not separated when shuffled. The common thinking is that you have to either re-rip them from a CD or use third-party software in order to do this.

Does anybody know how to do this natively in iTunes, which is where this functionality belongs?

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Doug's Apple Scripts for iTunes "Join Together" script (dougscripts.com/itunes/itinfo/jointogether.php) works very well, and it's free. It just bugs me that I can't do this inside of iTunes. It's probably some obnoxious Apple restriction. –  Alan Aug 18 '09 at 13:02
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up vote 2 down vote accepted

Sure you can do this...

Just group select the files you want> right-click> Get Info

Go to the Options tab> "Part of compilation" to yes and "Gapless album" to yes This will make iTunes treat them as 1 and play them continuously

Hope this helps...

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However what if you use the Compilation tag specifically to identify compilations vs complete single artist albums? –  Diago Aug 18 '09 at 13:00
    
I may be doing something wrong, but your suggestion (thanks, by the way) does not seem to work in shuffle mode, though it does play the two without a gap (or cross-fade) in non-shuffle mode. –  Alan Aug 18 '09 at 13:01
    
Sorry I miss understood then... I believe if you leave off the Part of compilation, that will give you what you are looking for... If I understand correctly this time :) –  Mike Fielden Aug 18 '09 at 13:06
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