My Favourite- and one I use to “explain” what unschooling is about is School of Rock (Widescreen Edition). It shows how by appealing to a passion you can learn almost anything.
Some other favourites that appeal to homeschooling families:
The Secret of Roan Inish A wonderful movie I can watch over and over.
The Wild Parrots of Telegraph Hill My favorite movie of the year.
The Pippi Longstocking Collection (Pippi Longstocking / Pippi Goes on Board / Pippi in the South Seas / Pippi on the Run) Always seems to come when discussing homeschooling. Lots of fun for all ages.
Uncle Buck I saw this recently- I was a bit taken aback by strong language that I notice is prevalent in 80’s kid’s movies- they seem to have a harshness to them. Having said that- the movie has a lot of themes that fit in with unschooling and being yourself.
Never Cry Wolf This was a favorite book when I was a kid- and the movie really holds up well.
Whale Rider A beautiful movie on so many levels
Please feel free to post your own suggestion and recommendations :) !!!