I think the most memorable is probably The Wolf of Wall Street but it was nowhere near as awkward as it could have been. My sister and her husband wanted to see a movie with the family in theaters. Luckily the uproarious constant laughter from the packed theater was far more manageable than the awkward silence that would have happened with an at-home watch.
What really got me was that a whole group of my friends had planned on seeing it the week before, but one very difficult guy insisted that he would not go see a “boring movie about financial crime” and made such a huge fuss that we finally agreed to see American Hustle instead, which was a very tame movie “about financial crime” funny enough.
After, that guy said he was bored for the entire movie (despite the fact that American Hustle was actually pretty good). If it wasn’t for the fact that The Wolf of Wall Street is exactly the kind of movie you want to see with your friends and not your parents, and that American Hustle would have been a perfect movie to see with the family, I’m not sure it would stick out in my mind so much.
My best guess is the Tales to Tremble By scary story collections:
Each story had some creepy art by Gordon Laite:
A lot of this fits with your descriptions from the best of my recollection.
Edit: Removed paragraph about potential third scary story series containing spider egg story, just realized that one was from Scary Stories to Tell in the Dark 3, so Tales to Tremble By and its sequel is my only guess here.