To me it depends a lot on the music... if it's more complex, or has more emotional depth I can usually continue to enjoy it almost indefinitely and get something new out of it each time.
I'm sad to admit Led Zeppelin has lost some of it's charm after many listening, which makes me sad because I enjoyed it so much in the past. I've found a lot of Pink Floyd stuff is complex enough that I'm still enjoying it and noticing new things after many decades of listening to it. Watching videos of Floyd playing live also opened up a whole new appreciation for the music.
Lots of the music I enjoyed as a kid/teenager had themes I can only now understand in my late 30s, and didn't really appreciate or fully grasp back then.
Overall, a lot of prog really seems to have enough complexity to remain interesting for a long time. Most of Tools albums, I seem to not enjoy much at first, but enjoy more, and notice more things each time I listen, even after hundreds of listens.
The same music that is complex enough to remain interesting over time, usually doesn't compress well and is really damaged as a low bitrate MP3. I've found those same albums I listen to most year after year are the ones I sought out lossless versions of.
I'm sad to admit Led Zeppelin has lost some of it's charm after many listening, which makes me sad because I enjoyed it so much in the past. I've found a lot of Pink Floyd stuff is complex enough that I'm still enjoying it and noticing new things after many decades of listening to it. Watching videos of Floyd playing live also opened up a whole new appreciation for the music.
Lots of the music I enjoyed as a kid/teenager had themes I can only now understand in my late 30s, and didn't really appreciate or fully grasp back then.
Overall, a lot of prog really seems to have enough complexity to remain interesting for a long time. Most of Tools albums, I seem to not enjoy much at first, but enjoy more, and notice more things each time I listen, even after hundreds of listens.
The same music that is complex enough to remain interesting over time, usually doesn't compress well and is really damaged as a low bitrate MP3. I've found those same albums I listen to most year after year are the ones I sought out lossless versions of.