Yeah, I’m 10 years behind the times.
Is there any way to tell iTunes that 5 or 6 songs should not be chopped up on shuffle mode?
I mean really. Hearing Polythene Pam, followed by say,* Light My Fire* isn’t what I expected.
I selected said group of songs in iTunes, right clicked and then saw “Consolidate files…” but that didn’t even seem to do anything.
Thanks.
ETA: This is an iPod shuffle that I got as a present. Which I never, ever, would have selected for myself.
If you ripped it from a CD (and you’ve still got said CD), the easiest way may be to reimport it. When you’ve got the CD in, you can select the tracks in question, and then go to “Join CD tracks…” under the “Advanced” menu. Then reimporting the CD will create a single MP3 containing all eight tracks back to back to back. If you don’t have the CD, you might also be able to find a third-party piece of software that will allow you to concatenate all of your files. Google “join MP3 files” or “join AAC files”, depending on the format you’ve got them in.
If you want to keep all eight files as separate items, though, and just have your iPod know what to do when “You Never Give Me Your Money” comes on… I got nothin’. Sorry.
I have the CD. “Join CD Tracks” is greyed out? 
If I really wanted to do this, I would probably open the files in Audacity and just join them up manually.
I’m somewhat astounded that Mr. Jobs and his crew didn’t anticipate that certain songs could (must!) be stitched together to prevent this unwarranted bastardized flow. It seems like a no-brainer for the likes of Apple.
No one there considered that “Heartbreaker” and “Living Loving Maid (She’s Just a Woman)” must always follow one another?
I’m disappointed.
It’s a shuffle - it’s designed to play songs in random order. Still, you can:
There used to be an option to shuffle by album rather than by song but I can’t find it now. Consolidate files moves the underlying files around, it doesn’t affect the way they appear.
It’s cute that you say “side 2.” My favorite first use of digital selection is that I could skip “Revolution 9.”
But the original order of releases is so grooved in your head – not to mention a critical part of the musical presentation – that undoing it is a mind fuck.
I’m not such a Beatles maniac, but I was given Meet the Beatles when it first came out. I bought the CD when it was released, and the ordering followed the British release, as I was told by some Beatles nut.
You just prehear the sounds or energy of the next song, after having listened to the sequence eight million times. MP3s have undone what it took pop music 50 years to achieve, the full-length “concept album.”
A Beatle said somewhere that Sgt. Pepper’s wasn’t a concep album, but just a bunch of songs. Not so sure about Pet Sounds.
Just my opinion.
Did you select all of the songs that you want to join together? For me, the Join option is grey when I’ve only got one song selected, but when I shift-click to select several songs, it becomes available.
And how!! Don’t even have to skip it, didn’t transfer it! Love The Beatles but that ‘thing’ is stupid, pretentious, indulgent, worthless garbage (Yoko!) 
I have an iPhone 4 but I’m told (hate Apple) that the ‘music’ function of it is essentially an iPod. There is a flag you can set in iTunes when you right click and do ‘Get info’ that says ‘Part of a gapless album’. However I think all this may do is not insert a pause when the whole album is selected & played, I don’t think it will exclude it from single song shuffle. Which isn’t even really what you want anyway. But like someone said, single song shuffle is what it is and it can’t really make an exception for songs like that.
Greyed out no matter what I try.
This would be a deal-breaker for me. I have a bunch of audio books and I couldn’t imagine listening to a novel with the chapters shuffled. I guess I could edit them into one gigantic mp3 file but then I would lose the capability to jump to a specific chapter. I’ll upgrading to an Android in a few months so I will have to pay attention to this feature. Shuffle is fine for interchangeable pop songs but try to imagine listening to a symphony with all of the movements shuffled.
And are you looking at your library, or at the songs on the CD? The CD should be listed under “Devices”, and if that one is selected, and multiple songs in the list are selected and “Join CD Tracks” is still not available, then… I give up.
You have to manually join two songs into a single file for this - all song-shuffling software assumes one file = one song. You can make a playlist, but what you can’t do in any player software I’ve seen yet is make a playlist of playlists (where single songs automatically count as singleton playlists).
As for Heartbreaker -> Living Loving Maid, I was stunned to see that the digitally remastered Led Zeppelin boxed set didn’t have the two back-to-back, breaking with years of Classic Rock radio tradition. Which I suspect originated because on an LP of Led Zeppelin II, the pause between the two songs is so short (with no fade-out/fade-in on either song) that it was easier to just play the two tracks back to back than mess up trying to end it after just Heartbreaker.
In fact it didn’t even have Living Loving Maid on it, at all. 
OK. I figured it out. You need to join the tracks before importing them into iTunes. After you’ve imported them there’s no way to join them.
So, I’m happy.
I also figured out how to make playlists on the iPod shuffle, which is great since sometimes I’m in the mood for James Taylor, Simon and Garfunkel, Gordon Lightfoot, etc. and sometimes I’m in the mood for Deep Purple, The Doors, The Kinks, The Who, etc.
All is good. Thanks for the help everyone.
Audiobook files are tagged differently and don’t shuffle.
As someone already mentioned, audiobooks are different.
Also, when listening to a symphony, you would not pick a random shuffle, but would pick the album or playlist for that symphony. You then have the choice of listening to it in either standard mode or in shuffle mode. You certainly don’t need to shuffle ever if you do not want to.
The OP’s question was along the lines of "When listening in shuffle mode, is there a way to ‘force’ a song to immediately follow another one. That is a little more complicated, and is easiest done, as he ended up doing, at the time of import.
delete
This!
I had to do something similarly with the Chef Aid album since the track breaks do not match up with the song breaks and to join songs that sound better together.
My favorite use was being able to listen to just the odd-numbered tracks on Double Fantasy. (IOW, only the John Lennon songs.)