iTunes won't choose music to sync onto iPhone

[orbitalmovment]

When I go to sync a playlist onto my iPhone, it tells me that I have to much music in that playlist and then nothing happens after that. I remember the first time I put a playlist onto my iPhone it asked if I wanted iTunes to automatically choose a playlist at random from my playlist becuase it was to large to all fit. I don't have the time to pick through 20gigs worth of music to try and make a playlist on my iPhone.

What happened? It doesn't ask me that now. I've since updated and got the latest version of iTunes and iPhone software. I restored it and still nothing.

Is there a option somewhere that somehow got un-checked? I'm doing this on a PC.

[Youngbinks]

That's weird that it's not working for you any longer but here is how to set up a Smart Playlist. It allows you to set up certain parameters for which songs are selected.
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Choose File > New Smart Playlist.


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To add songs that match specific rules, make sure “Match the following rule” is selected, and then choose options from the pop-up menus. To add more rules, click the Add (+) button.
Tip: To duplicate a rule, hold down the Shift key while you click Add.


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To make the playlist a specific duration or size, select “Limit to” and set options.


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To include only songs that have a checkmark next them in your library (and that match your rules), select “Match only checked items.”


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To have iTunes continually modify your Smart Playlist as songs are added to or removed from your library, make sure “Live updating” is selected.


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To create your Smart Playlist, click OK and then name the playlist.