Dungeons & Dragons: Honor Among Thieves is always a good mention.

It's a fun and very accessible movie.

Dungeons and Dragons: Honor Among Thieves

I didn’t think the trailer looked good and it felt meh, but I ended up loving the movie a lot.

Originally, Pirates of the Caribbean. A movie made because of a Disney ride seemed like a stupid idea.

The Cabin in the Woods. Only seen it once so far and I'm still floored thinking back on it and how well it did its thing.

Clue

Movie based on a board game? Blegh

But it's awesome. Tim Curry, Madeline Kahn, Christopher Lloyd, Lesley Ann Warren

They Live.

WWF wrestler discovers magic sunglasses and yuppie aliens. It's a John Carpenter film and has one of the longest fist fights.

Tucker and Dave vs. Evil. Looks like another dumb Netflix original, but it was one of the best horror/comedies I've seen.

Speaking of the genre, big nods to another one - Little Evil.

It Follows - just read the premise of the film and tell me it doesn't sound dumb... Then go watch it

Oh and Colossal!!! Ann Hathaway stars in this bizarre and very deep movie about a giant monster that can be controlled from a playground. Amazing movie. Trust me

Tremors

Looks like a B movie, cheesy horror flick.

It's got a great cast with supurb acting. The script is easily one of the tightest ever written. Every line is important to the overall story. And it's just fun to watch.

https://m.imdb.com/title/tt0100814/

Osmosis Jones.

A half-and-half cartoon and live action film with Chris Rock as the titular character from the late-90s/early-00s. The movie was a flop, but I think it had more to do with lousy marketing. It was actually pretty good and a fun way to look at how things affect the human body.

David Hyde Pierce as the enormous Pill was a great choice, and Bill Murray was hilarious.

Sucker punch.

Looks like a mindless action with titties, but it's actually a good movie. Give it a try if you haven't.

"The Adventures Buckaroo Banzai Across the 8th Dimension" 1984

Great script, great cast, young Johnathan Lithgow and Christopher Llyod, Peter Weller in one of his best rolls, and bonus Jeff Goldblum as they new guy.

Whole thing is still a perfect package, looking like a B movie you'd totally skip.

Con Air

It is absolutely not well written but I just love how the film and all the actors are completely aware of how dumb the entire thing is.

Oh, and casting Chief Engineer Miles O'Brien as the jerk that everyone hates is the icing on this guilty-pleasure cake.

There are so many movies I could list but for now I'll go with About Time (2013). Everything about it makes it seem like it would be a dumb sappy romcom but it manages to hit hard.

EDIT: This is the type of image they used to market the film, which is really misleading.

Free Guy

Generic video game movie stuffed with trendy references and fanservice is actually a really good singularity story

Disney's "The Black Hole". It came from a time just after Walt Disney had died and they were still figuring out their shit.

So they made an extremely dark SciFi flick with a cute robot that appeals to children which is such a weird combination, but I liked it a lot. I can't even say why.

The U.S.S. Cygnus looks fucking badass, too. One of the best ship designs in a SciFi movie, change my mind.

The Unbearable Weight of Massive Talent and Renfield were absolutely amazing and I think they fit the bill

The Long Kiss Goodnight

https://imdb.com/title/tt0116908

Geena Davis and Samuel L Jackson. He said in 2019 that it was his favorite role. It was released after a flop for Davis and director Renny Harlin (then her husband), and may have had poor press related to that.

It has an unlikely hero, plenty of action sequences, some fun performances (I had to pause it after a funny line from Brian Cox cracked me up), and heart. Solidly entertaining. But low expectations might help.

Pandorum. At a glance it like like just another bad sci-fi, but it's really good horror sci-fi mind fuckery with a fantastic twist. Dennis Quaid is great in it.

The Jumanji sequels. You are going to take a cult classic and "revive" it by changing the premise to be a video game? Stupid. But, it was much better than it should have been.

Abraham Lincoln: Vampire Hunter

Surprisingly good action and a decent plot to boot.

Velocipastor! It looks and seems like it'll be a parody but it was super engaging and fun. Went into it thinking it would be watched between gaming rounds and eventually turned off, but I ended up quitting the game to full-screen that shit!

I loved Hudson Hawk. The story was bonkers, the musical numbers were entertaining and had a great ending.

Event Horizon... terror in space? Worse the Alien? can't be.

but it is haunting and PTSD inducing, very well made

I'm giving away my age, but Benny & Joon. A story about two mentally ill people falling in love, and the script isn't even that great, but all the actors really sell it and it is such a quirky heart warming and funny movie.

Conan the Barbarian (1982) has no right to be as good as it is. On paper, it's a dumb sword and sorcery flick with a body builder who could barely speak English in the lead. But everyone involved does an incredible job, from the acting to the directing, to the score. It's a crime that Destroyer trashed up the formula, and we never got Conan the King.

Doom 2005 wasn't bad.

I’ve not seen it since it came out but Crank (2006) is a terrible, dumb action comedy that has no right being that entertaining. It’s sequel Crank High Voltage is less good but also still enjoyable. I should rewatch them see if that’s rose tinted glasses or not!

Clerks. It should be some stoner Seinfeld flick but it actually lines up pretty well with La Divina Comedia and the dialogue, although sometimes a bit clunky, is very well written.

I thought Dude, Where's My Car? was very entertaining - maybe not a cinematic masterpiece, but way better than the 9 out of 10 reviews I read that all said it was the worst movie they had ever seen. I'm not exaggerating - they didn't just say it was bad, I remember nine of the ten literally called it "the worst movie I've ever seen."

HOT TUB TIME MACHINE!

Previews and premise made it look like it would be stupid, but that movie is pure gold. I've never been able to understand how such an entertaining movie had such a low rotten tomato score. So much great stuff is going on.

Warrior with tom Hardy/joel edgarton/nick nolte. Marketed as a shitty MMA cash grab. It’s fantastic. Also has like 2 finales that crescendo so hard one after the other.