I haven't been doing as much rewatching lately, mostly because I've been plowing through a lot of TV shows I either never saw or haven't seen in ages (currently working through
My So-Called Life, Freaks and Geeks, and
The No. 1 Ladies' Detective Agency all at the same time

).
Some titles I frequently find myself watching again and again:
Love Actually
All the President's Men
Who's Afraid of Virginia Woolf?
Shaft (the 1971 version)
Cars
Transformers (the Michael Bay version)
Eddie Izzard: Glorious
Stardust
The Family Stone
Twilight (it's like a train wreck... I'm horrified, yet I can't turn away)
Firefly and
Serenity
McLintock!
Music and Lyrics
And on the rare event that there's a snow day and I can't make it in to work, I curl up on the couch with a big mug full of hot chocolate and watch the extended version of all three
Lord of the Rings films.