Funny thing is, the people who first saw it in college thought it was just the right age for it, and the people who first saw it when they were 7 thought it was just the right age for it, and the people who first saw it in their teens thought it was just the right age for it…
I don’t think it was about age.
Here’s John Scalzi’s take on The Princess Bride as “possibly the ultimate in comfort watches”:
One of the main things he praises about it is its rewatchability: not that everybody likes it, but that, for those who do like it, it holds up to repeated viewings.
I saw it my sophomore year in college in my university’s chemistry lecture hall. Somehow the student association got the film reels and played it for free a few months after it was released in the theaters.
It was unlike anything else I’d ever seen. It was funny and clever and poked fun at all the tropes. And it didn’t take itself too seriously, but also didn’t descend into camp like Airplane! or Spaceballs (which came out a few months before the Princess Bride).
One thing not mentioned yet is that it has an excellent score that is well-utilized. It’s a little bit over the top at times, but in a way that fits the scenes perfectly, e.g. the swordfight, and Inigo’s confrontation with the six-fingered man.
It’s one of a small handful of films (Galaxy Quest is another) that is both a parody or sendup of a particular genre, and a good, faithful example of that genre that can be enjoyed on its own terms.
All of the best parodies are also good examples of their genre. Another one would be Blazing Saddles, right up until the weird ending.
I loved Blazing Saddles and Galaxy Quest and I saw Galaxy Quest many years after it came out. PB just didn’t do it for me and maybe it’s because I was unfamiliar with the genre generally.
The Congress is a fever dream of a movie, I don’t think any extra knowledge of The Princess Bride would help you understand it. I enjoyed it but wouldn’t say I really “got” it.
As to The Princess Bride itself, I would have been 8 when it came out and for a long time I put it in the same bucket as movies like The Neverending Story and Labryinth – that is, movies that came out when I was too young to appreciate, and that my peers seemed to love a little too much which made me not like them.
Every time I’ve rewatched it I’ve enjoyed it more. At this point I put it in the same bucket as “The Big Lebowski”, which is “movies that are better on the 4th, 5th, and 6th rewatch.” I find it to be well-paced, light-hearted, fun, and somewhat timeless.
The Princess Bride is campy, cheesy, dumb, terrible in places, but always in an amusing and entertaining way. A description I’ve heard before is that a piece “parodies itself.” But parodies can be mean or affectionate. This one is so loving a parody it more than makes up for the bits that make me cringe, and they are many (with the Fire Swamp leading the list).
And the quotable lines are almost worth it, in and of themselves. We toss them about all the time in my household - most recently a few hours ago when my wife commented, “murdered by pirates is good.”
Toss any of these lines about, and you’ll nearly always strike a chord
“You keep using that word. I do not think it means what you think it means.”
“Mawwage is what bwings us togethah today.”
“I’ll most likely kill you in the morning.”
“He’s mostly dead!”
That’s a great description of both films.
I was 35 when it came out. I enjoyed some of the performances in a “we’re going to have fun with this” hammy sort of way, but otherwise the movie did not (and still does not) do anything for me.
I’m almost certain that I never even heard of the movie when it was in the theaters. I was way too busy studying engineering and going to Dead shows to be aware of much else. In 1996 or so I became friends with two new coworkers who were in High School when it came out. We had a different coworker named Juan Montoya who was kind of a doofus so you can guess what joke they constantly made. I finally asked them what the hell they were talking about and they were surprised that I had to ask. I saw all of the memes and references when I was first on the internet right around that time. I was honestly expecting to enjoy it.
Even if that’s a cliche, what makes it work in TPB (IMO) is Peter Cook’s unexpected, ridiculous accent. “Mawwiage…”
Is it even a cliche? Or rather, was it at the time?
I’m not sure that it is, but @Q.Q.Switcheroo apparently feels differently.
It’s common enough to have its own TV Tropes page (which admittedly includes examples of officiants skipping ahead to the vows for other reasons). And look where the page quote comes from 
:
Without the fire swamp, I couldn’t call a capybara an ROUS.
It’s my favorite comedy film of all time, I recently saw a showing in the theater with 3000 people and Cary Elwes talking. It was an amazing experience in a theater with 3000 like minded fans, all knowing every line but letting the actors deliver them without shouting them out. Anticipation, laughter, fun; it was a great viewing experience.
I think of it as a celebration of fairy tales, not a parody.
It’s just a good, fun movie. My kids also love it (ages 21, 22, and 27).
This was from before COVID. There was a car show in the area(as evidenced by the cars I saw running around town). I was passed by a smallish economy car painted a deep custom bluish-purple with the license plate MNTOYA . It took a while to come up with the color name then it made sense.
It was an Indigo Montoya