I've gone so far as to record the tapes straight into flac and listen to those on my ipod instead.
I know every warble, wow, and flutter from those old tapes, I even have a rough chronology in my mind of when the tapes developed their defects. The too hot car stereo in my friends camero that summer day... that lousy walkman that tried to eat it.
I can play the modern digital copies in the right order till the cows come home and be unmoved but even a whisper of the noise between tracks on one of those old tapes and its '94 again and I'm back on the beach at sunset with that girl in my arms...
See the story from a day or two ago about how badly CDs are being mastered.
Personally, I listen to a lot of non-English music and I'm beginning to wonder if part of the reason might be that non-US music companies seem to be much less likely to utterly destroy their music in the quest for illusory volume, because the "foreignness" is not something that I particularly care about either way.
Try your experiment on a CD from the mid-nineties. It is highly likely that what you are experiencing is a result of atrocious mastering, and not a digital-vs-analog result. Note that it has to be a CD that physically dates from the mid-nineties, not merely an album from the mid-nineties, as companies have been going back and destroying the old music on re-releases.
Of course that doesn't address the issue of your personal memories and if you like that, hey, great. I'm not going to complain or tell you it shouldn't be that way.
Now the target is iPods, Cars and maybe Radios. So they mix to make it sound good in those scenarios (well, in lots of cases).
Also, whilst this sounds interesting, knowing more about the experiment might help. AAC compression can do more than just compress the music (might be doing some other form of levelling, and/or adding punchiness in some other form).
Until this problem goes away, CDs are no longer the choice of discriminating audio enthusiasts.... but not because "digital" is worse than "analog", but rather because "destroyed digital" is simply bad. Right now in the "digital vs. analog" war, CDs aren't bringing their A-game.... they're not even bringing their D-game.
A further thought occurs to me; maybe people prefer "Crappy 44KHz originals with clipping softened by MP3" to "Raw crappy 44KHz originals". This ought to be controlled for, if it wasn't, as this might be the rational choice even by audiophile standards. (Yes, it's crap vs. crap, but there may yet be a distinctly less crappy one.)
Everyone knows the best way to hear music is through the soft clipping of a tube amplifier.
I've got a http://www.mcintoshlabs.com/ tube/valve amplifier. I rip my CD's to FLAC, stream via a squeezebox, into a monitor-grade DAC-1 (i.e. neutral sound) into the amp. So it's bit-perfect digital, which is then given character by the amplifier.
Mcintosh were once the king of tube amplifiers. They moved away to solid state back in the late 70's / early 80's. Then, as part of an anniversary, they decided to revamp some old tube designs. To their surprise, they liked the sound, do they bought some of the designs back.
I remember reading they were stunned at the quality of the actual tubes - obviously back then they were using tubes that were made using 30+ year old manufacturing techniques. In the meantime, the Soviets had actually put a lot of work and research into tubes (as they were late to the silicon game)... Anyway - Upshot is that you can get tubes nowadays that are extremely high quality and reliable - perhaps moreso than in their peak.
I've also noticed there are a lot of tube iPod docks now as well: http://www.google.com/search?q=tube+ipod+dock&ie=utf-8... .. They are reasonably cheap - As for the quality, I can't imagine, but they are around.
Edit: The place that tubes (KT88's and the like) are also still found is in guitar amplifiers - for the same soft clipping reasons mentioned above.
They cost $2000-$3000
Encoding to MP3 @ 128Kbs will apply a low pass filter (so that more bits can be used to encode the lower frequencies) and high freqeuncy sounds can sound smeared. I would guess one or both of these factors could be responsible for reducing harsh sounding treble.
I'm guessing of course but if right, I wouldn't say the MP3 was better. Merely, it masks a horrible sound to begin with.
However, 128Kbps in an encoder designed to encode as rapidly as possible will not have that result, and that's the usual case.
Also, hooking up a decent set of headphones to an iPod and that itself can be a "nice audio system". The stats on the iPod are pretty good, it's the headphones that are crap. I have a Creative Labs Zen myself, which has an inferior interface, but has even better audio statistics, and the best audio experience you can get in my household are my ~$100 monitor headphones hooked up to the Zen. That's pretty fine. Run a great MP3 through it and you'd never know it's not the original CD. Run a mediocre MP3 through it and you'll cry.
You can't really hear the different instruments and the layers of sound unless you have reasonable quality speakers. I've tried purchasing good, expensive headphones, but nothing beats the experience of listening to music on a set of wooden-casing surround sound speakers (arranged optimally around the room, of course).
BTW, this is coming from someone who is definitely not an audiophile. Currently listeing to Piano Man on my crappy MacBook speakers.
Its the same as photography, film, like cassettes, vinyl etc is no better than digital, its just different. The medium is an important part of any art form, possibly with the exception of literature. For the visual and music arts I have seen this phenomenon often but I am not sure if it applies much to books. The medium is largely the same I suppose - we've moved on from writing on pigskin, but for the past few hundred years and book today is much the same as a book from anytime, only the content has changed. The arts move, and are moved by technology at different paces. Possibly the Kindle will change things, but it hasn't had enough time to know yet.
You can hear the difference between MP3 and CD/FLAC sources quite easily, so I've come to like CD/FLAC.
I started off listening to vinyl at about 12, CD/tape until 1998, then Napster in 2000. Now I buy CDs and rip to FLAC, if possible, and hardly listen to MP3s.
By the way, albums like Madonna's Confessions on a Dance Floor sound really bad on MP3, because it's been mixed to a very full sound and compresses poorly. I don't know if that's the producer (Stuart Price) or the mastering people, but a bootleg of this album made from MP3, I ordered by mistake, was really really bad sounding.