Yes. If there's something I like for some reason, it tends to get a lot of playtime. This tends to be films I like for visual reasons (Metropolis I have seen an unreasonable amount of times at this point).
I very rarely rewatch movies or TV shows, but for whatever reason, I do re-listen to the same music over and over and frakken over. I've seen my Dexter DVDs once, maybe twice. I've listened to the soundtrack ten billion times.
I don't anymore, but as a kid I would watch the same Star Wars and Indiana Jones and Doctor Who shows over and over. When I worked in a video store for four years I would put in the Star Wars and Harry Potter movies over and over again.
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.