Not to the same extent as you but… I had a five-CD capacity boombox (until sadly I accidently melted it 
) which had a song-shuffle function, that I took advantage of. The only disadvantages being the 5-CD limit and the very loud shuffling of CDs between tracks…
When ‘shuffle’ came out, I thought it was the coolest thing on earth (still do). I had been doing my own version of it for years, dating back to albums, even.
I had, I dunno, 500 or so albums on shelves. Once in a while I would get in a shuffle mood. I’d close my eyes, grab a record, and place it on the turntable. Then I would open my eyes and place the needle on a random track, all the while being careful to cover the label with my hand so as not to reveal the album or artist. I’d do this for several songs in a row (different album each time). Sometimes I’d accidentally catch a glimpse of the label and get pissed off. 
Yeah, I’m not weird.
mmm
You must listen to a lot of Yes, or maybe Pink Floyd
I have two players now with a combined 500 discs, that can both shuffle and trade off tracks between them. Crossfaded, even. Individual tracks can be dropped out of the rotation. Pretty good setup if I don’t feel like choosing something.
When I got my first CD player (in 1991—it was a 6-CD changer), I thought the “random mode” was a very cool feature, and that it would bring new freshness to old familiar albums, if I could hear the same songs in a new and unexpected order. It did that some, but I didn’t (and still don’t) end up using it anywhere near as often as just playing CDs straight through in the intended order, because usually, that intended order is what flows best.
I’d say “yes” if you deliberately made them (as I did) so they had unexpected combinations of music styles – Bach rubbing shoulders with Hendrix, etc.
This is cheating, but MP3s were widely popular before the debut of the iPod in 2001. I attended college from 1996-2000 and during this time I had quite a bit of music on my computer. Shuffling through these was quite easy.
My first CD player was specifically a 5-discer for that purpose. I had a CD set of national anthems of the world, I didn’t want to listen to them in (alphabetical / track) order, as I’d know which one was next (yeah, I know, same thing for my non-anthems CDs, but bear with me), I liked the idea of playing “Test the Uber-Nerd”, if I had my anthems CDs on random shuffle, I could see how long it takes for me to guess which anthem it is (instead of knowing because if, say, I’d just played Nepal, I know that this must be Netherlands). I usually average getting it within the first bar or so now (many the first note or two). Unfortunately, my CD set was a 6 CD set, but, I was happy.
Extreme geekery? Where??
With the rest of my music, combination of the above disparate statements. I’d make mix tapes all the time (translated now to Mix CDs (is that the term? I still call them “mix tapes” even if they’re on a CD) but put a hell of a lot of thought into the order of them - I’d assemble my mix tapes like how most people assemble jigsaw puzzles - I’d start with the obvious songs (in a jigsaw, it’s the corners and edges) to lead and end with. For instance, “Assorted Songs 1” starts with Platinum Blonde’s “It Doesn’t Really Matter” (and has since high school), the woman saying “Are you sitting comfortably? Then we’ll begin.” in a calm manner at the start of the song is a natural way to start the collection! Similar way of choosing the end song, there are a few songs that make great ending songs of a CD. I’d then pick what songs go best after the first one/before the last one, and build the collection that way. It has the disadvantage that slow songs tend to get lumped together (but I may luck out that there’s a song that starts slow and ends fast, or vice-versa, to get me out of the jams)
Amen. Being able to program the playback on CDs made Double Fantasy a much more enjoyable listen, as I was able to eliminate all the Yoko songs.
The kid and her husband bought me a new CD copy of Abbey Road for Christmas. Son-in-law put it in the player and hit shuffle. Weirdness ensued.
I had a 6-disc changer in the early 90s. The options were to randomly play songs from one CD or all 6 CDs, or to program in a list of songs and play them in the order that you programmed them in. Long before there were MP3s or iPods, I had thought the BEST. FEATURE. EVER. would have been to give it a list of songs that was a subset of everything on those 6 discs, and play those in a random order.
Yeah, playlists. A lot of us thought that up years before it existed.
I have a couple of 400-disk carousel players and before I moved to my present abode, I had them full and would often play them randomly. They had an interconnect which allowed both players to shift between them. Since I got my 42-inch flatscreen tv an DirecTv I haven’t unpacked the cds. Anybody wanna buy the carousels? Just kidding, onthe sale offer.
I have a first generation MD player/recorder, the one that had a metal case instead of the plastic case, and it also recorded … bought it at a Navy Exchange. Beautiful little toy. I was so sad when the format did not take off in the US =(