It's fascinating because like many memes it didn't make sense in the first place.
I don't think anyone really gave a shit if they heard that (actually quite catchy) song. But everyone had to act like they were completely screwed over by hearing the song.
I don't think it was ever that the song was disappointing but the fact you went somewhere expecting something only to see the trademarked, "ah ha, fooled you!"
It's a great song. The longevity of the very friendly prank is probably perpetuated by how great the song actually is.
An example of this: When I was in my last year of secondary school a few years ago my physics teacher was explaining how she was completely dumbfounded that a little 13 year old just picked up a microphone (Doppler effect demo) and belted out an almost completely random pop song from the 80s? I explained the meme but it's still bizarre how people who would otherwise have no idea who Rick Astley is know all the words to the song.
It's also a great song, so I honestly enjoy being rickrolled for the most part.
It's more benevolent than the Goatse man [NSFW] that used to be common on Slashdot via disguised links. In the end they had to put the domain next to the link text so people couldn't get caught.
Slashdot was user-moderated, so you just needed enough people to find something +1 Funny or +1 Interesting. And rick rolls were always +5 Funny. The fun really started with the meta-moderation though. I’m still not sure how that experiment turned out.
It’s strange to think how changes in moderation and up-voting have led us from Slashdot to Digg to Reddit (and HN).
As someone who was a pretty early Slashdot user -- apparently, my user number there is 3616 -- I think the meta-moderation mostly worked. That's not a universally shared opinion. :) But I thought that the discussion level was consistently decent throughout the 2000s, and I think the moderation system definitely helped there. On the other hand, the multiple layers of user moderation require at least a handful of users to be regular "comment gardeners," which probably requires a fairly large user base to be viable.
(I drifted away sometime around when they were bought by Dice; I can't swear there's a causal connection, but it seemed to me the site kind of lost its mojo through the 2010s.)
It's very apparent that it is absurd right up front so everyone gets it. The likelihood of a misunderstanding is fairly low.
The song is so bubbly and happy there's no apparent negative connotations.
And it's a nice song generally.