"Maybe I'm Amazed" is OK, but to me, it sounded like a "Paul Hit Ballad" tacked onto an album of off-the-cuff, living-room recording.

That may sum up my feelings about The Wall — as a Poster Boy for classic rock radio.

The movie is full of great lines … and few of them work out of context, but still are somehow awesome.

Re: Glengarry Glen Ross — does that count in this context? A movie spawning actors who went on to win Oscars is different from a movie containing several actors who had already won the award.

An example of how "dated" doesn't automatically connect w/ outdated fashion:

I hadn't really thought about series that were in both B&W and then color. Good point.

One major demarcation with TV
B&W vs. color.

"Twilight Zone" has been mentioned multiple times in the comments. I think one reason that type of show endures is that it addresses timeless philosophical themes.

I think you could find specific examples of TV, music, movies, etc., in any decade from '60s onward, and make a case for longevity, or lack thereof … so I guess generalization depends on specifics.

This looks promising
But first: I'm sure someone else already pointed this out(1), but it's "Ironside," not "Ironsides."

I think "Hammered" by Motorhead could be the best metal album of the 21st century.

"What are you talking about? Lennon in the late 80s was considered kind of washed up."

Jeff Buckley.

You've actually listened to "The Wall" in its entirety? I envy completism.

Dozens of possibilities (or more)
Most intriguing to me among those included here:
1. Buddy Holly
2. D. Boon
3. John Lennon

I thought about the uppers episode as I was reading this feature, too.

Def Leppard is an example …
… of a band I have a hard time (1) hating or (2) liking.

I agree, "One Chord" is probably a good start.

Don't know how I missed this one. Awesome.
At first I found myself just scanning for references I (a) already knew and (b) involved my favorite B-Boy cuts.

I can relate to several things in your post, gee-man … in the same age range; the "new music sucks" bitching (several years ago friends in my age group said something similar, and I said, "There's good and bad music released every year …. you just have to find the good new stuff")