Unable to move more than one song at a time

For some reason, iTunes has stopped allowing me to move more than one song at a time to playlists or my manually-managed iPod. I can grab as many songs as I want, but when I drag them over to the sidebar, i don't get the little green plus sign that means you can add the songs.
If I only select one song, it woks fine.

Did you by any chance uncheck the the boxes beside any or all of the songs in the library? Unchecked songs won't play in a playlist or the library unless you select them individually: iTunes: Understanding the Symbols Next to Songs
Holding down the Control key and clicking the checkbox next to a song in the library or a playlist will toggle the marks for all the songs on or off: : iTunes 7 Keyboard Shortcuts for Windows

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    Holding down the Control key and clicking the checkbox next to a song in the library or a playlist will toggle the marks for all the songs on or off: : iTunes 7 Keyboard Shortcuts for Windows

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