[jbbosco]

Hi,
I have a 60Gb video Ipod, and have large custom playlists that I like to listen to in shuffle mode. Some songs on the playlist must be heard back-to-back to really appreciate them, like 'Heartbreaker' and 'Living Loving Maid (She's Just A Woman)' off Led Zeppelin II. How can I glue these songs together so they always play back-to-back, no matter what? Is this something I can only do outside of iTunes?

[Earth Mk. II]

You can join 2 (or more) tracks together when you encode the album on iTunes. Pop the CD in, select the tracks you want joined, and Advanced > Join Tracks. The option is only available while importing a CD.

I'm not sure what other utilities for this exist outside of itunes.

[Cadaver]

I believe you can tag each song for gapless playback, but to always keep two songs back-to-back when shuffling is something I don't think you can do (without physically converting both into one file).