Off the top of my head... Little Nicky and My Boss's Daughter. Little Nicky is not funny at all, but I like it's late 90s/early 2000s charm to it. My Boss's Daughter is one of those rare movies where it's juvenile humor makes me laugh. Don't know why. I feel like I lose brain cells just watching that movie, but can't help but laugh.

There are other bad movies I like, but I'll mention them later.