I don't really watch good movies. I pretty much spend my time seeking out the worst movies I can find and watching them because they're very entertaining. That said here are my top recommendations:
Anything with Arnold Schwarzenegger: The man is a comic genius and is great at not taking himself seriously. Pretty much everything he's in has a great campy vibe to it and is a joy to watch.
Bad Boys I&II: These movies are so over the top and ridiculous. It's almost offensive, but moreso, it's just fucking hilarious. I love Will Smith, and this is him being an obnoxious jackass at its finest since Men in Black. Watch them and laugh your ass off.
Wild Wild West: Jim West, desperado. Rough rider, no you don't want nada. It says something about me that I know all the lyrics to the title track of WWW. Probably nothing very good. Anyway, it's ridiculous, it's bad and it's really entertaining.
Heavy Metal: The 80s compiled into a big, awesome animation with great 80s pop/metal over top of it. It's just fun to watch.
Troll 2: The quintessential "so bad it's good" movie. Bad acting, effects and story. It's a wonderful bag of failure (see it in theatres if you have a cinema that does cult classics nearby).
Josh Kirby: Time Warrior!: This is my ultimate recommendation. I found this in a bin. This is a six-part series of movies that are so full of hilarious nonsense and bad everything that it's so bad it's good, then back to bad again, then is SO bad it's back to hilarious. I've seen Troll 2 many times and this many times and Josh Kirby is legitimately worse in every way. It's so bad that they had to summarize half of the first movie because they ran out of editing money, then spent half of the second movie finishing the first one. I die laughing almost every time I see any of these movies. Go watch them.
Happy watching. I salute you.