I really like "greatest hits," singles collections and other sorts of compilations on CD. However, I'm not too hot on placing the songs on them out of chronological order. Here's the story:
Tom Waits' Used Songs collects 16 choice cuts from his career between 1973 and 1980. Waits started out with some rather safe singer-songwriter material, like "Ol' '55" and "(Looking for) The Heart of Saturday Night." Then he started moving towards the material that he is more known for: from powerful ballads to avant garde-jazzy-blues. Hearing this period be jumbled up on CD is a tad frustrating for me. Why? I like to hear the progression of an artist, album by album, not just a random mixture of songs.
In the case of Waits, hearing his voice on a song like "(Looking for) The Heart of Saturday Night" (which sounds more like a Bruce Springsteen knock-off) be followed by "Muriel" (which showcases Waits' trademark croak) doesn't flow that well to me. Both songs are amazing, but the jump in styles isn't. Maybe the goal with Used Songs was to go with the best flow of songs (the soft/quiet to the loud/wild and everything in between) regardless of when they were released. Hmph.
Luckily, with iTunes and my CD burner, I simply rearrange the songs to how I see fit and go from there. While that's easier for me and my usage, I wonder why so many compilation CDs jumble up songs by a single artist.
As a lot of artists/bands progress with making albums, you hear some very big differences in sound production. The production often gets glossier over time, thus making the initial albums sound young and rather archaic by comparison. For example, would it really make sense for a Cher compilation to have the orchestral-pop of "I Got You Babe" be followed by the dancefloor techno of "Believe"? Not to me.
I guess I'm more of an anthology kind of listener. If I like an artist very much, I want to hear the progression more than the equivalent of pressing the 'random' button. I like to hear how an artist developed and understand how maturity doesn't happen overnight. I like hearing the slow process even if it renders dodgy results. I think that's worth hearing.