Imaris
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No, but I use ratings. I have an autoplaylist with ★★★★★ songs, with ★★★★ and above, and so on. There are currently 72 songs in the five-star playlist out of a total of 3456 songs in the main audio library.
And before, I used to do something similar, as you described; I needed it for music on my phone. I would choose one or two songs from each band, from each album, so that my phone would always have "representatives" of my different music in case my iPod ran out of battery or something else happened. Now my iPod is broken, and I've abandoned this idea altogether – there's too much music, and if I choose songs the way I'm saying (which, by the way, is a headache because with many bands, you can't just choose a couple of songs; you want this one, that one, and that other one), it would take up a lot of gigabytes and wouldn't fit on my phone.
And before, I used to do something similar, as you described; I needed it for music on my phone. I would choose one or two songs from each band, from each album, so that my phone would always have "representatives" of my different music in case my iPod ran out of battery or something else happened. Now my iPod is broken, and I've abandoned this idea altogether – there's too much music, and if I choose songs the way I'm saying (which, by the way, is a headache because with many bands, you can't just choose a couple of songs; you want this one, that one, and that other one), it would take up a lot of gigabytes and wouldn't fit on my phone.