How can I duplicate a song in iTunes?

Why do you need to duplicate them inside the library?

If you’re trying to make a track play more than once on a playlist, you can just drag the songs from the library to the playlist again.

Aahh, sorry, I should have been more specific. I want to make a compilation/playlist/mix for a friend, and I want all of the songs to have matching artwork, organized track numbers, and the same album name. (That way it’ll look like a coherent, curated album when they drag it into iTunes.) I don’t want to edit the metadata of my original songs though, I just want to copy them so I can make a “mix album.”

So to clarify, I would definitely like to double the files themselves, not just their play count in a playlist. :)

@sinscriven is right. You can add the same song to a playlist multiple times. When I do it a dialog box pops up and asks me if I want to add duplicates or skip them.

Did you create a new playlist? Once you have done that you can drag any song from your music library tab into it in any order you choose.

Is that what you mean???

If you change the file type in import settngs, when you right-click on the files there will be an option to create MP3/AAC whatever version.

For example, if all the songs are AACs, and you change import settings to MP3, then you can create MP3 versions of all the files.

Your library would have both the MP3 and AAC versions.

@Seth: I could be wrong, but I don’t think the metadata gets written into the disc, so any CD you put into a new machine will have that blank ‘track 1’ type of info until the data is pulled from Gracenote/CDDB. Discs aren’t identifiable on their own.

so any CD you put into a new machine will have that blank ‘track 1’ type of info until the data is pulled from Gracenote/CDDB

Then I would unplug the computer from the Internet and see if you could keep the generic track names.