Holy crap, where to begin. I've seen a bunch of dumb movies over the years! But yeah, I'll try to group these by theater as opposed to recording/streaming/ cable.
Movies:
Cool World - still can't believe i watched all of it. It's also the answer to the Bill Simmons-inspired dis if I ever meet Brad Pitt: "Hey, you were great in Cool World!".
Beavis and Butthead Do America - date movie suggested by a girlfriend at the time. I liked the show back in the day, but damn this was stupid. We broke up soon after.
Cyborg - plot holes. Plot holes everywhere. ****ty acting (kinda expected it, but still).
Light of Day - another date movie from last part of high school senior year. Michael J Fox and Joan Jett in a band movie! What could go wrong?
Legend - high school math honor society trip to Houston. We'd just had what was to this DAY the WORST service I've ever had or seen at a restaurant (Bennigans, I think), and had retaliated in typical high school kid fashion - we didn't tip JACK ***** Anyway, the only redeeming thing from this movie was a smoking Mia Sara.
Not in theater:
Gymkata - movie night at high school buddy's house. This was so epically bad that my friends and I very quickly switched to MST-3000 mode... before that was a thing. It also spawned the term "Dan movie", which became a catch-all adjective for ANY horrifically terrible recommendation, very much to the host friend's embarrassment.
Vanilla Sky - for such a great cast, this fell SO flat. I still don't know what the **** this was about.
World of Warcraft - bored and drinking...alcohol couldn't save this viewing - and I'd actually played the game for a few years.
I'm sure there's more, but playoff hockey is on.