Shows or movies you can watch over and over and over...

Arrested Development. I've probably watched most of the episodes 5-6 times on DVD. 30 Rock is getting there for me, too.

 

A lot of stuff, but the thing I've re-watched the most in my life is Marge vs the Monorail episode of The Simpsons. It's the perfrect television show. There isn't one second of it I don't enjoy.

I've re-watched Twilight Zone episodes a lot.

As for a movie, I've re-watched 2001 A Space Odyssey more times than I can count.

 

I don't re-watch movies an awful lot, at least not start to finish. TV shows are much more in line with my re-watching attention span. Most nights I'll put on an episode of AD or 30 Rock while I'm going to sleep.

 

Friends - I bet I've seen most episodes five or six times.
The Office (before it sucked)
30 Rock
Cheers
Seinfeld

Movies: Off the top of my head, Almost Famous, Hoosiers, Christmas Vacation, Good Will Hunting

EDIT: Mad Men. Duh.

 

The Paper, Broadcast News, Twister, Volcano, Outbreak, The Professional, Poseidan Adventure (original), any and all Airport movies, When Harry Met Sally, Pretty Woman, Perfect Storm, Ocean 11

 

TV
Get Smart
Seinfeld

Movies
Blazing Saddles
The Graduate

 

TV Shows
1. Everybody Loves Raymond. The parallels to my life and other people I know hit too close to home.
2. COPS. This is reality TV. None of that bullshit you see now. Also unintentional comedy at its best.

Movies
1. Raiders of the Lost Ark. They don't make 'em like this any more.
2. Unforgiven. Still maintain the best last 20 minutes in movie history.
3. Caddyshack. I can mute the movie, do all the lines, and still laugh my ass off.
4. Fargo. Just because.
5. A Clockwork Orange. Yes, I am twisted like that.

 

Mine would be "House of Games." I've seen it at least 15 times.

 

Movies;

Rounders
Caddyshack
Blazing Saddles
Oceans 11, 13
Major League

 

TV:
Jackass
Johnny Quest

Movies:
Shawshank
Casino
Pale Rider
Any Bond movie with Roger Moore as 007
Diner
Any of the first 3 Stars Wars films made

 

I think Down Periscope could fit this category.

 

TV shows: Home Improvement, the Cosby Show, Gilmore Girls, Big Bang Theory, Glee, Will and Grace. How I Met Your Mother is starting to get up there as well.

Movies: Twister, When Harry Met Sally, Love Actually, V for Vendetta, Independence Day, Star Wars, Monty Python and the Holy Grail, Almost Famous, Mulan, The Lion King (don't judge, Disney made some damn fine movies in the 1990s), Apollo 13, Empire Records, A League of Their Own.