As oz describes:
four jobs I've had: Documentation developer, sysadmin, maintenance coder, IT Monkey
four movies I could watch over and over: There aren't four. The best I can come up with is the Lord of the Rings trilogy, which I have enjoyed watching back-to-back-to-back in its extended form (though the 12 hour sitting is a bit exhausting!) and Primer (which requires multiple viewings to make sense.)
four places I've lived: Toronto, Lausanne, Yellowknife, Cambridge Bay
four TV shows I love to watch: Firefly, Whose Line Is It Anyway (british version), West Wing (seasons 1-4 only), and I'm told I'll love Battlestar Galactica, when I get around to watching it.
four places I've been on vacation: Spain (mediterranean coast, for my honeymoon; wouldn't go back), Niagara-on-the-Lake (for my anniversaries; definitely going back), Jasper (in Alberta, at the base of the Marmot Basin ski resort; a wonderful place to ski), Nelson (in the interior of BC -- very pretty town with great people, better coffee, and even better accomodations Chez Little Brother).
four websites I visit daily: Look to your right. Slashdot and Boingboing get visited more than once a day, and I browse my RSS subscriptions at least four times a day.
four of my favourite foods: fresh homemade pasta, french toast, steak frites, what's in front of me at the dinner table
four places I'd rather be: working for a company that didn't actively resist organizational change as much as it does, skiing in BC, living the life of Riley in a Tuscan villa while independently wealthy, on the Paris/London/New York jet set.
four books I've read more than once: Bradbury's collected short stories, Understanding Comics by Scott McCloud, Snow Crash by Neal Stephenson, The Atrocity Archives by Charles Stross.