That Movie Podcast's Zack and Jake ponder over which 5 movies would be worth taking with them should the apocalypse come (because that's obviously what they'll be pondering at the time).
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Oh my Goodness! What has this world come to? Let the Apocalypse come and hopefully they won't have time to pack the movies.
Yes, just kidding but to me the choices were that bad!
I'd definitely take Fight Club, The Big Lebowksi (Donny, you're out of your element), and Pulp Fiction, which I just wrote about in length @ my site.
One of my choices would be Last of the Mohicans with Daniel Day Lewis. The filmography and sound track was so beautiful it took my breath away. Of course Serenity would have to be the other one to remind me of my friends and family. The other 3 movies I'd have to think about.