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Still looking...
Thanks for your replies, but the search goes on.
#2 (closet monster) was too disturbing to have been an episode of Goosebumps. It was definitely a movie: that much I remember. I watched the trailer for Cameron's Closet (couldn't find the entire film streaming online) and I'm pretty sure it's not the right movie. The kid in the movie I remember was older, and the film's image quality was higher. It wouldn't be They; it would be a pre-2000 movie. I'm leaning toward 90s.
#3 (boy goes into painting) isn't Waxwork. I just watched it. (Tangent: Wow, so many 80s movies have characters who are horrible people! The rich brat protagonist here [seems like he's supposed to be a teenager, but he's played by the main actor from Gremlins, clearly in his mid-to-late 20s] tries to gets his maid to write his college papers for him, and he's supposed to be the sympathetic hero? All of the characters were obnoxiously sarcastic, contemptuous, letting off nonsensical remarks posing as one-liners...)
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