I’m going to add From Noon till Three, with Charles Bronson.
Edited to add: Hello and Goodbye.
Silly comedies that I enjoy over and over again:
Dodgeball
Galaxy Quest
Josie and the Pussycats
Mystery Men
No Strings Attached
Not Another Teen Movie
Summer School
Zoolander
Roadhouse
Stripes
Fifth Element
Zoolander
Galaxy Quest
Carrie
Blade Runner
Highlander
Willy Wonka and the Chocolate Factory
Jurassic Park
Iron Man (1 and 2)
The Mummy
The Green Mile
Sherlock Holmes (1 and 2)
Harry Potter (pretty much all of them, though I can usually drag myself away if necessary)
I’ve never run across Galaxy Quest on TV, but if I had, it would probably be on the list.
The Fifth Element
Galaxy Quest
Repo Man
Primer
Bunraku
A Christmas Story
Many, many more I could add to the list, but those [del]5[/del] 6 are a good representative sample.
Oooo-eee! These are two of my all-time faves! I’ll bet you’d also like The Uninvited (the 1944 version with Ray Milland). I watch that one over and over.
Roadhouse
Death Wish I, II, or 3
These are movies I should hate, but I always watch them if they’re on TV and hate myself, instead.
Also, Band of Brothers. I can’t turn on the TV before noon on Memorial Day, Independance Day, or Veterans Day because I know that will be on and I’ll end up sitting on the couch for the next 6+ hours.
Haven’t seen it. Will tonight! Thanks, ThelmaLou.
My current one is Bridesmaids. I love that movie and it’s one of the have to watch movies that I don’t own. When I’m flipping thru and I see it, I have to watch it! I keep going, “well, just a few minutes. Okay, I’ll turn it off when you see Jill Clayburgh and her character’s crazy paintings.” Then part passes and I’m still watching, and then its the section at the party where Wiig’s character and Helen battle over the microphone…and then I tell myself, “well, I’ve gone this far, I have to stay for the trying on the dresses!” And then that’s it, my brain has just settled down and made itself popcorn.
It’s like the old Paula Poundstone poptarts thing–
“Inside there are three pouches of two. This is what happens to me: I open the first pouch, and I eat one tart, and I enjoy it very much, as naturally I would. And then I feel, Well, I have to eat the second one or it will go stale. Well, now I’ve eaten two, and it’s no longer just a snack, it’s a meal. I figure I may as well eat two more. And then finally I’m just like, Well hell, I don’t just want two pop tarts hangin’ out in a box. I eat the last two just to tidy up, really.”
Bridesmaids is like Poptarts to me. 
Before that it was School of Rock. And Shaun of the Dead.
Do let me know if you like it. 
I’m not even sure I think its that good of a movie, but: The Big Year , with Steve Martin, Jack Black and Owen Wilson.
It’s been playing on HBO lately, and any time I see it in the guide, for some reason I just can’t not watch it. Over the past couple months I’ve watched it, or had it on in the background, probably 5 or 6 times.
*Snatch
The Matrix
Dumb and Dumber*
off-topic Hey Calwdio - did you hear a new Big Year record this year?
Lots of the ones already mentioned above. In addition:
Last night Hart’s War sucked me in again. I’m waiting to add Red Tails to the list as soon as it goes into heavy rotation.
Coinkidently enough I was just thinking along this line as I spotted Baz Luhrman’s Romeo and Juliet at the library. A movie I can watch repeatedly.
A bit differnt, most of the time when I spot such movies being broadcast, I don’t have to stay until the end - I mean I know the end.
Princess Bride makes my list too, liked it from the first time and every other time. Others too that others list.
I am only somewhat surprised that so many people cannot resist re-watching over and over again movies that I almost regret watching the first time.
Blazing Saddles
Hot Fuzz
[ul]
[li]Sergeant York[/li][li]Shawshank Redemption[/li][li]Pride of the Yankees[/li][li]Pride and Prejudice (Firth & Ehle version)[/li][li]Pretty Woman[/li][li]Seven Brides for Seven Brothers[/li][li]Iron Man[/li][/ul]
My Cousin Vinnie
Coming to America
Fiddler on the Roof
Godfather (any of them, even 3)
Shawshank Redemption
The Blues Brothers