How to keep only unique titles on my iPod

Question

I've a moderately extensive music collection, with complete discographies of several artists. As it turns out, there are duplicate songs on several albums (for example, Santana performs Black Magic Woman several times, to put it lightly). I've currently got my itunes set to randomly select about 6 gigs of music from my library to push onto my iPod every sync. Is there any way to tell iTunes to put only one copy of each song onto my iPod (So, only one copy of Black Magic Woman, instead of the 10 currently pushed).

Bonus points if you can figure out how to not make it apply to the same song title by two different artists (Satellite by Dave Matthews Band versus Satellite by Guster versus Satellite by Lena).

I'd like to stick with using iTunes on OS X, if possible. If it helps, I'm using a 6-GB iPod touch.

Answer 1

Sometimes you have to answer the question by saying you shouldn't answer the question;

I'm going to go out on a limb and say you shouldn't do what you're trying to do. If there is such a large problem with dupes, you should consider figuring out why you have so many dupes in the first place. Entire discographies is one good reason why this is the case.

Do you really like everything by a particular artist so much that you have to have every single release portably/at all times? If that's the case, why is hearing such a good song multiple times so much of a problem?

Here's an active reason why you don't want to do this, at least in my perspective.

I like the "atomic" nature of albums. After listening to it a few times, I begin to like not only the songs, but the order in which they're presented. If you start cutting songs out, you're going to find that you don't like that album as much, all because you saved 3MB on a large storage device. You can save that much space by crunching your library into a slightly lower bitrate/and perhaps a different format. (mp3 -> aac, just don't re-use the aac files anywhere else.)

Surely when you listen on shuffle, you are affected by duplicates such as this even less? On an iPod touch, I know that when you play by artist without shuffle, you'll hear the same song multiple times because of the same title and the alphabetical playback order.

In a nutshell, my suggestions:

1. Don't do this.
2. Don't do this.
3. Don't do this.
4. You can't have one physical file exist in multiple albums (to the best of my knowledge), and you'll lose the atomic nature of a given release if you start excluding songs.
5. Don't put every single album you have for a given artist on your iPod. Pick the best.
6. Listen by album instead of by artist, or;
7. Listen by artist on shuffle.

Answer 2

It's a bit of a manual approach and will require some habit forming, but you can simply uncheck the duplicates as you import them and only sync checked songs to your iPod. Realize that this won't be fun in the short term if you decide to compulsively go through your entire collection right now and implement this, but it is a foolproof method of keeping duplicates off of your iPod.

The first step is File -> Display Duplicates.