Not even guilty pleasure…just love
U-571. I don’t care about the historical complaints. No one said it wasn’t fiction. Fast-paced. Great cast. Subverts a lot of expectations as far as the cast goes.
Passenger 57. I’m pretty sure these are the only two movies from the time I’ve listed and they both have 57 in the title. Anyway…just fun. And whats the runtime? Like 70 minutes? Doesn’t dawdle.
Blair Witch Project. I thought it was incredibly realistic. I found it in a VHS discount bin years after its release, and I didn’t expect much from it. But dayum!
The Lost Skeleton of Cadavra (2001) a very funny stupid little movie. From the company that brought you “Zombies of Mora Tau” and “Lawrence of Arabia.”
Magnolia. I walked out of the theater shaking.
I think Tom Cruise is a weirdo, but after that movie, I can’t bring myself to dislike him.
Butterfly effect. I like the idea of changing the past, and liked the idea that everything he tries fails or makes it worse in some way.
Romy and Michelle’s High School Reunion. I LOVE this movie. I don’t even know why. It’s pretty silly. But fun.
evolution it’s just a funny dumb comedy with some people who were famous for other things …
the funniest thing was I was telling my friend I went with " you know “a big star” should be in this and not 2 minutes later he showed up for a medium-small part that about 8 scenes total
we laughed and people thought we were laughing at the movie …
it was dan Akroyd playing the governor
Ditto! It’s a classic!
Pleasantville.
Another huge favorite of mine, probably since Roscoe Lee Jones narrates, Little Children.
The Rock. Yes, it’s ridiculous, yes, it has as many action movie cliches as they could squeeze in, yes it has Nicolas Cage. But I love the corny lines and the performances of the leads (Cage, Connery, Ed Harris, and a great supporting cast too).
I enjoyed *The Adventures of Ford Fairlane * so much that I saw it twice in the theater. On the same day. Still own it on DVD.
Sgt. Bilko. I don’t know why, I just do.
Phil Hartman probably has something to do with it, and maybe that sense of post-Cold War/pre-9/11 levity and optimism. An attitude that I might encapsulate as something like “Oh, that lovable Sergeant Bilko, he scammed his way out of the Gulf War, but that was just such a quick flash in the pan steam-roll against such a ridiculously out-matched opponent, who could really blame him?”. In fact, now that I think about it, I’m tempted to give the film a mention in “Classic” movies or TV shows with situations or premises basically impossible today. The humor would have to be so much darker if set in the GWOT era.
‘Clerks’. A cinematic masterpiece. 
It’s one of the few Michael Bay movies I enjoy. It wasn’t as good as my teenage memory of it but it’s still a decent action movie.
Kindergarten cop: The endearing parts are very movie-of-the-week but they work, especially the scene with the ferret. There’s also a scene with a scene about a serious topic that engendered more anger than I would have expected. I don’t know if “love” is quite the term but it’s a lot more watchable than you’d expect for an early 90s Arnold comedy.
Office Space is also pretty good. You can see it being part of the same cultural wave that includes Fight Club, The Matrix and American Beauty which all came out the same year.
Enemy at the Gates and Swordfish were also nice. Enemy at the Gates is very stark as if fitting for a movie set in the battle of Stalingrad. Swordfish is a heist that’s not big on restraint.
Blade 1 & 2.
Braindead
Gross violent disgusting and funny as hell
I think your mention of Enemy At the Gates helped me hone in on what I’m looking for. As soon as I read it, I thought “YES!! Thats one!!”
A dumb(ish) premise* (within the time frame i mentioned) turned up to 11 without trying to be pretentious. So Face/Off, which I DO love, wouldn’t qualify cause its definitely a little pretentious.
*I mean…all the Russians are English and the main German is American, right??
If Magnolia counts as a stupid little movie, then my submission for a stupid little movie from the late 90’s that I really like is Boogie Nights.
*Magnolia *is many, many things, but “stupid” and “little” are none of them.
Old School (2003) has its moments. Dust in the Wind is the second song Will Ferrell has changed to my ears, after The More Cowbell Song which is apparently actually called Don’t Fear the Reaper.
“Yer my boy, Blue!”