I think the weirdest disney channel original movie is "Quints" from 2000. It's often forgotten by people and it barely aired as a re-run.
The story is about a girl that gets quintuplets for siblings. Now, you'd think the story is like "oh she got siblings and now she's jealous over not getting any attention". But no, that's not the story at all.
The girl is like 13 when she gets her siblings, so she's already been an only child enough time that her parents not anymore having time for her is kinda nice for her. And she does not have any resentment for her siblings either, because... well, she's a bit too old to feel resentment over them "stealing" her attention. What instead happens is that she becomes some sort of spokesperson for the quintuplets. Cause her parents, to earn some extra money now that they have six kids, sign up a deal with some diaper company or something and the quintuplets gets to be their models. They get a bunch of free stuff, also because quintuplets itself is really rare, the media likes to come to their house and make reports about it. But the girl gets annoyed over the fact that they keep treating her five siblings as if they are one unit, rather than 5 individuals. She's like "STOP JUST REFERRING THEM AS 'THE QUINTUPLETS', THEY HAVE NAMES!!" Like, she goes around switching their cribs just to see if their parents can tell. She uses the babies as models for her art, and then she puts out these illustrations of baby heads in the school art show.
Speaking of art: She has the creepiest art teacher that always have such strange comments and I felt so uncomfortable every time he opened his mouth. She also has a friend who has neglectful parents and that is never resolved. Like, is he ok?? I got quite concerned with him.
Also the girl's parents win "parents of the year" or something and when they go, they ask why they didn't bring the quintuplets (because they wanted a bunch of screaming babies at a fancy gala??????) so the girl and her two friends have to carry all 5 of them in baby carriers taking the subway to the city hall.
This movie is on D+. Watch it if you can. It's... an experience.