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I use iTunes DJ pretty frequently, it serves a great purpose for when you have no specific artist/album you wish to listen to, nor a loose collection of songs based around a single genre (Genius).

This issue is at it's worst when I'm driving, and wish to listen to music; Voice Command only gives me the ability to pick an artist, album, or playlist.

How best am I able to create something which uses my entire Music library, and can quickly, easy, and perhaps most important of all, safely, begin playing any random item?

Additionally, shuffle should be turned on, or some other aspect of randomization should be used as part of the accepted solution. One other important aspect is that I've explicitly mentioned the use of Voice Command, which only exists on an iPhone (3GS and 4).

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I use the take 5 app to queue up whatever playlist I want from my iOS device. It starts up the shuffled music once time expires or I can unlock the screen, swipe twice to unlock and expire the delay. It's great for gas stops or phone calls too. – bmike Aug 1 '11 at 22:26
Make a playlist with everything, call it "playlist". Then use voice control to say "play playlist". If shuffle is turned on it will be random. If not, shake your iPhone. – Paul Eccles Aug 2 '11 at 7:26
Shaking necessitates the phone being unlocked and the iPod app being in the foreground, yes? (I think I might have that 'feature' disabled...) – Jason Salaz Aug 2 '11 at 17:09

I use an app called InstanTunes.

It doesn't have voice command, but it does use a selected Source playlist to generate a random playlist from. Then uses this playlist as a Queue. Whenever you like you can add songs to the playlist which are added into the Next Song position of the playlist.

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