I also have to add: Labyrinth
I am Legen
Close Encounters
Napoleon Dynamite
Stripes
Watchmen
Shaun of the Dead
Hancock
Sky Captain and the World of Tomorrow
Beastmaster
Ronin
Some of these I haven't seen, a few (Hancock, I Am Legend, Shaun of the Dead & Watchmen) are too new (for me at least) for me to consider them a favorite yet. I've watched Watchmen 2 or 3 times already and want to watch Hancock again, but it's still too early to tell if they're something I want to watch a couple times a year.
I haven't seen Stripes in years. It's a good movie but I wasn't interested in getting it on DVD. I couldn't past the ten-minute mark with Napolean Dynamite ... simply not my taste in humor.
I have about 400 dvd's and enjoy most of them. These are some I watch over and over.
I didn't take into account the DVDs that my wife claims as her own. Between us both, we have a lot & I wouldn't try to guess what the total is since we've been buying DVDs for over 10 years. There's other movies I like (Harry Potter, Constantine, Lord of The Rings) but they're "hers" so I don't touch them unless she wants to watch them too.
I also enjoy TV series as well like Friends
Roseanne
Fresh Prince of Bel Air
Band of Brothers
Rome
Well, "Favorite TV Shows" is a whole 'nother discussion, but Band of Brothers is up there for me, as well. I'ld add The Simpsons, Futurama, Penn & Teller's B.S. and Mutual of Ohama's Wild Kingdom with host Marlin Perkins as shows I simply don't get tired of watching repeatedly.
I got burned-out on Fresh Prince when my girls were about six months old (they enjoyed watching it), since a couple of channels would run about 8 episodes back-to-back. After a few months, I'ld seen each one about four times, so it's something I can live without now, but maybe in a few years I could start watching it again. I feel the same way about Friends, seeing it often over a short period of time due to the fact that so many stations would run multiple episodes every day.
I really enjoyed Roseanne during its first run, but have had a hard time getting into watching it in syndication.