Ok for the sake of the question, I'll stick with movies only. Less variables that way.
1. Inland Empire
Three hours of confuzzling awesomeness. Even if I was stuck on the island forever, I could spend my time just trying to figure out the mystery.
2. Moulin Rouge
I think I'd just have to take this one. My first ever favourite movie. It's beautiful. And that way I could sing along and become a pro singer.
It makes me smile. Love love love.
4. Eternal Sunshine of the Spotless Mind
Funny thing is I don't even own this... yet. But I want to. And I'd like to take it to the island thank you very much.
5. Buying The Cow
In choosing this last one, many others crossed my mind such as The Virgin Suicides, Mulholland Drive and I almost went with 21 Grams... but then I remembered my fondness for Jerry O'Connell comedies. I would need my Jerry O'Connell. I know this movie is just silly and stupid and without much artistic merit... but I can't help but love it.