Can I "merge" tracks to play in order even during random play?

[zombieflanders]

Does iTunes have a setting to only play certain tracks together with other ones, both in the app and on iPods/iPhones? In other words, if Track A comes up as random, the next track will always be Track B, not another random track. Some good examples would be:
Live performances with fade-ins or conversations (like Johnny Cash's Folsom Prison sessions and most electronica)
Radio shows (like BBC Radio's Essential Mixes)
The Star Wars soundtracks, where I want the Fox Fanfare to always lead into the opening theme
Soundtracks with dialog included, such as Lock, Stock, and Two Smoking Barrels or Fear and Loathing in Las Vegas
The Abbey Road medley of "You Never Give Me Your Money" through "The End/Her Majesty," or "Back in the USSR" fading in to "Dear Prudence"
I know this is an odd question, seeing as how random is supposed to be totally random, and I know it's a long shot, but I don't want to smoosh tracks together with an editor or anything like that. I can live with total random play, but I'd love it if there was a method of doing this.

[jzuena]

I've always wondered the same thing. Since when you add music iTunes does its gapless playback scanning, it has an idea of what songs should have no gap when played back-to-back. So why can't it use that info to play them back-to-back when playing randomly? The closest setting I can find is "Part of a gapless album" under a song's options. I don't know what checking this will actually do, though.

[Muncher]

I've always wondered the same thing. Since when you add music iTunes does its gapless playback scanning, it has an idea of what songs should have no gap when played back-to-back. So why can't it use that info to play them back-to-back when playing randomly? The closest setting I can find is "Part of a gapless album" under a song's options. I don't know what checking this will actually do, though.

I think it may have to do with how iTunes loads the songs before playing (i.e. no break in between). The free live Coldplay album is gapless, but I never checked that option because when playing the songs in order I never hear a break.

[jzuena]

I think it may have to do with how iTunes loads the songs before playing (i.e. no break in between). The free live Coldplay album is gapless, but I never checked that option because when playing the songs in order I never hear a break.

Even studio albums like the first Van Halen album, which I ripped myself external to iTunes will play Eruption / You Really Got Me without a gap, and that option isn't checked. But it has to do something. It might be worth trying it with a lightly loaded iPod to see if it can get songs that belong together to play together even during shuffle play.