but with some things it doesn't at all
Presumably at some point they were held in high regard or it's more how the type of person in such a field may act. Like oil jobs make more than most jobs outside of engineering degree or lawyer or doctor jobs and you can start working them at 18. But you'd only know if you lived or worked in areas full of oil people and that also means you're almost certainly a hardcore redneck stereotype.
That sort of goes with physical labor in general, before it was taken by Mexicans it was still held in lower regard because even if a plumber might make way more money the types that worked those jobs weren't exactly charismatic fine art loving people, and especially in the boomers days, tradesmen had a reputation of being sleezy con artists taking advantage of women. Most men in those days knew enough and had enough self respect to not let a contractor handle most jobs, whereas today an electrican will be hired to install a ceiling fan or microwave for $90 an hr.
Of course it also ebbs and flows, look at how people thought of computer programers or nurses in the 80s vs today.
As for cheerleaders I'm sure it's because in the pre-internet days those were the prettiest ones who'd end up being married off to the successful men.
Also people love entertainment way more so it's why working at a rental store or record shop held as much respect as working at a bar despite being a literal minimum wage job.
You can sort of see a genre change too when it comes to restaurants and a huge reason for that is how it went from a job for poor whites or Mexicans and is starting to be seen as something cultural elites do thanks to Anthony Bourdain and shows like The Bear
And it's not a hard and fast thing, the HVAC guy in my childhood town wears a suit and drinks wine and is the reason we can have the usual Christmas shows and activities going on, and while he has a low class job he's obviously very high class.