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I think most bands that are "cringey," "bad," or "for middle schoolers" are unfairly labeled as such. Most of these bands actually start off with really strong debut albums, and get their foot in the door, which is what makes them famous in the first place, and then produce bile and shit because the music industry is run by controlling, greedy bastards (and most bands sell out anyway), then the band's shitty later work is what gets seen by most people, and the band looks like shit. I think this is what happens to a lot of "bad" popular bands, like, say Slipknot. Everyone thinks Slipknot is super trashy, but their first album was really cool. It's just that they get judged for by bland radio friendly stuff their producers made them put out once they got big.
I also think that the ravenous, retard fans do a good job running their favorite things through the mud. This isn't even just bands. Fandoms like Homestuck or Steven Universe are usually full of such insufferable 10 year old shitheads that run around making the whole franchise look retarded. Which sucks, because sometimes, those things are really cool, but don't get as much of a chance from people as they deserve, because their reputation is tarnished.
Also, I think that people will associate bands or fandoms with their cringe experiences when they were fans of those things, and think they've outgrown said things. I think this happened with a lot of post hardcore music and pop punk, like My Chemical Romance or Blink 182. It's not nearly as cringey as people let on. I think people just remember those bands, and remember being in middle school getting rejected from prom and sulking around a lot.
