Playlists

Sometimes I wonder if I have odd listening habits when it comes to music. This question relates to the context of certain songs and whether I choose to play or skip them. For example, if I'm listening to Jagged Little Pill (by Alanis Morissette, of course) I prefer to play the album in order without skipping any songs. But if Ironic or You Learn came on a randomized playlist, I'd most likely skip them and probably remove them from the list in the first place because I'm so burnt out on them. But if I heard them on the radio or in the presence of other people, I'd enjoy them. Likewise, when listening to Rolling In The Deep, I tend to skip ahead to the next track if listening to Adele's album 21 but if it came on at work, I very much enjoy it still. I'm sick of hearing Katy Perry on the radio but sometimes I sneak her into my iPod and let her songs play through should they pop up on playlists.

It's an odd thing, context. And with that, I'm always trying to maximize how context effects music I love to make me love it more, whether it's current music or old music that I never hear anymore because they don't fit in anywhere.
On my computer and subsequently my iPod, I have dozens of playlists to suit any mood I happen to find myself in:
-Current/New Music (singles from within the last 3-6 months)
-Essentials (songs that are timeless to me. Though I try to keep this list fresh by changing it up every few months)
-Playlists by periods of time (I have an 80s playlist, 90s, 2000s, one for summer albums, spring albums, and playlists for more specific years)
-Playlists by artist (if I have a lot of songs by a particular artist, I'll take a bunch of my favourite songs by them for a playlist)
-playlists by genre (I have some playlists filled with songs that loosely fit into a generic genre. Dance, rock, light pop, pop/rock, electropop, folk/country and a new one I'm filling: electronic/ambient)

I'm always looking for ideas for playlists because I have so much music that I don't listen to because it doesn't fit into a specific context. I find putting my entire iTunes library on shuffle doesn't work for me. Maybe I ought to sneak a peak at some of my friend's iPods and see how they organize their tunes?