The core

The Room?

Army of Darkness, assuming self-parodies are allowed.

Twilight. If nothing more than to count the red flags and use it as a teaching tool for young teens on what not to do in romantic relationships.

Mom and Dad Save the World [1992] even as an 8 year old I understood this was a bad movie by so many standards but enjoyed it anyway. The injection. The muscly bird people. The fish people. Probably the first thing I ever saw Jon Lovitz in and I will forever see Spengo in any other character he ever plays.

Better Off Dead (1985)

Lane Meyer (John Cusack) is a teen with a peculiar family and a bizarre fixation with his girlfriend, Beth (Amanda Wyss). When Beth dumps Lane, he decides to kill himself, making bumbling attempts at suicide. Outside his morbid endeavors, Lane spends time with his oddball buddy, Charles (Curtis Armstrong), and befriends Monique (Diane Franklin), a visiting French student. Eventually, Lane resolves to race Beth's obnoxious new beau on the ski slopes, with unexpected results.

there are so. many. montages.

Snakes on a Plane

Phil The Alien

"Phil is an extraterrestrial with shape-shifting ability and telekinetic powers. After crash-landing in Northern Ontario, Phil befriends a red neck child, his father, and a talking beaver as he wanders the Canadian wilderness. Phil is soon introduced to the trappings of small town northern Ontario and adopts the persona and mannerisms of a stereotypical Canadian small town alcoholic while hiding from the ineffectual and mentally traumatized military general who is trying to capture him."

You can pick only one? There's so many!

• Yogahosers
• Llamagedon
• Velocipastor
• Holyman Undercover
• Kung Fury
• Empire Queen: Golden age of magic

Like choosing a top five is hard (yes I know that's six).

It also depends on who you're watching with. Any "bad" movie is the worst, or the best, depending on group ability to vibe with it

Evil Dead.

Idiocracy 😀

Mars Attacks

Rubber

Cocaine Bear.

https://m.youtube.com/watch?v=DuWEEKeJLMI

Street fighter (1994)

Battlefield Earth.

Volcano or Dante's Peak. Both are fun and bad in their own way

From the top of my head:

• Braindead / Dead Alive
• Tromeo and Juliet
• Death Machine

Top secret

Anaconda, closely followed by the first three movies in the Breenaverse, but probably Fateful Findings is the crown jewel.

From a vintage perspective, you can't do wrong with Space Mutiny, Werewolf or The Mole People.

But I always have a special place in my heart for Pumaman, the crapiest of heroes.

Mac and Me has a legacy thanks to Paul Rudd

Does Velocipastor count? They knew exactly what they were doing and made a masterpiece, but it is undoubtedly a bad movie.

Moonfall. There are some dull parts, but it's even more fun rewatching with someone who has no idea about the "plot".

Ice Pirates

Star Wars prequels.

Independence Day.

It was a 'cult revival' a few years ago. The only movie I ever walked out of. My buddy stayed and says he enjoyed it:

Kull the Conqueror: https://en.wikipedia.org/wiki/Kull_the_Conqueror

Miami Connection.

Troll 2

The Sharknado movies.

My favourite scene is when there was a flood but the streets were only about 10cm under water and then the sharks were swimming in the streets eating people.

Or the one were a one of the tornado sharks came flying to eat the main character and the dude chainsawed the shark in half.

Funny that, I just started a collection of entertainingly bad movies. We're at 100+ already. Highlights thus far include

Zardoz - Sci-fi Sean Connery in a future diaper.
Magic Magic - Horror movie Michael Cera.
Troll 2 - A Troll movie entirely bereft of trolls.
Showgirls - Stripper Nicholas Cage as played by Jesse from Saved by the Bell.
Critters 3 - Leonardo DiCaprio's film debut.
Breakin', Breakin' 2: Electric Boogaloo, AND Rappin' - no explanation needed.

Bring It On: Worldwide #Cheersmack

Birdemic

The Room is probably the correct answer but since that’s been said already I’ll go with Gymkata.

Thumbtanic https://www.youtube.com/watch?v=JYZdeh-x1F0

Plan 9 From Outer Space is the classic worst movie ever made, and that's why it's entertaining.