All of these are favorites because they influenced my childhood in some way...
The Last Unicorn
Labyrinth
The Dark Crystal
Everything is Illuminated
Whatever Happened to Harold Smith?
Dream with the Fishes
Little Nicky
Dogma
Garden State
Bill & Ted's Excellent Adventure (and the Bogus Journey too)
I also love The Crow, but it's not going on the top 10 above any of those. Donnie Darko and Eternal Sunshine would probably be in my top 50 but not top 10.
...so I guess I fit in decently well with the people who like depressing movies.

(Hey at least I didn't put Grave of the Fireflies on my list... but probably only because I still haven't seen it yet)