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I guess you have your artist's name and song title in the Name field in the Info tab. I'm sure the iPod app plays by the song name first, assuming you're not on 3.0(well, mine does).

mmm no. My music is well tagged and organized, thank you.

Most of my devices are testing devices on 3.0

And since the first iPhone, a random click always plays the first artist > first track.
 
And since the first iPhone, a random click always plays the first artist > first track.

Doesn't play the first artist and first track for me.

Turn off Shuffle, quit the iPod app (hold Home button for 5 secs) then click on headphones. Then quit iPod and click again.
 
I thought my location should fit my flag. I am a Brit and live in England.

I don't have any headphones with integrated controls so can't really play along but I can look at the iPod app and tell you what the first alphabetical song is

Atheist Anthem by Leftöver Crack

you are awesome
 
ABC by the Jackson 5. I'm now like Pavlov's dog -- every time I hear the song I automatically reach for my iphone.
 
I have no songs on my iPhone anymore...
I've also never plugged the supplied headphones into it...
 
If I leave my phone and come back and listen to something sometime the "now playing" is often
This is Hell - Permanence.

I dunno why, I guess I listen to it alot.
 
Ain't Necessarily So - Jimmy Somerville. Or could be by Erasure or Bronski Beat?? It's from "The Very Best of Jimmy Somerville, Bronksi Beat & Erasure" so not sure, exactly :p
 
A.D.I.D.A.S by Korn, then A.I.R. by Anthrax, then A.N.I.C by Sum 41.

Very irritating though, i leave my music on shuffle all the time, so why can't it pick a random tune when i hit the button?
 
'Ace of Swords' by Alan Parson's Project. Nice instrumental, but it can be jarring when not expected.
 
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