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The Money Pit.

Maybe darker than you are hoping for but the Final Destination films are like that, weird stuff going wrong killing people. Butterfly Effect also has this theme where every time he tries to fix something, something else goes wrong instead, although it doesn't always make sense.

The TV show Wings episode "Black Eye Affair" (season 4, episode 6) had Helen trying to prepare for a date where things just kept getting progressively worse.

The movie "A Film with Me in It" is a good one, it's a dark comedy. "Mousehunt" is a more lighthearted movie that matches your description.

Also, the episode 'Nosedive' from the tv show Black Mirror fits, although what goes wrong is in regards to the system where everyone has a rating on a 5 point scale that anyone they interact with can rate and change the average.

I guess almost every timeloop movie will have what you`re looking for.

Groundhog Day
12:01
Edge of Tomorrow
Predestination
Source Code
The Girl Who Leapt Through Time << Its an Anime if you dont care ;)

Meet the Parents
Meet the Fockers

Planes, Trains and Automobiles
Dirty Rotten Scoundrels