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I can't watch a movie as a 'pick me up' thing when I'm sad, it's just not what I prefer to do. I also really don't like rewatching movies often, so that makes this even less 'for me'. But! There is one movie I've seen about twenty or more times and it makes me laugh EVERY TIME, and that's The Emperor's New Groove and it is my favourite movie ever ever ever.
I need to buy Emperor's New Groove one of these days. It would be a pick-me-up movie if I owned it.
Adding the Truman Show to the list. Gets me so inspired to just pack my bags and go.
How To Train Your Dragon. My ultimate feelgood flick.
Miyazaki, Pixar, Wes Anderson(Life Aquatic), Bill Murray(Groundhog Day), or Korean(Going By the Book/200 Pounds of Beauty) movies. I highly recommend going on Netflix and checking out the ladder.
Peewee's Big Adventure always lifts my spirits. Though any movie I first saw between the ages of four and nine tend to comfort me because that was a really good carefree times so that's like a lot of 90s movies and some 80s The Goonies, Labyrinth, Forrest Gump, What's Eating Gilbert Grape, Gremlins, Edward Scissorhands, Terminator 2 (yeah I know wtf), The Lion King and any 90s Jim Carrey movies come to mind.