Last of the Mohicans. I love the story, actors, soundtrack, scenery...I could watch it over and over and cry each time.
Dirty Dancing. One summer I worked on Mackinac Island in Michigan, and every day for lunch we would go back to the big old house all the employees shared and watch this video. When it was over we'd rewind it and start again. It's just an addicting movie to me, and I don't have to watch it from the beginning, and I don't have to watch it all at one time.
The Horse Whisperer. I read the book by Nicholas Evans and was thrilled when it was made into a movie. I love the scenery (Montana) and the story about the horses. A friend from college lived on the ranch where it was filmed so I got to go visit the ranch and see the locations used. When I lived in I watched this a lot because I was homesick for MT.
Legends of the Fall (there is a trend here I see!). The scenery and story are great and I am a Brad Pitt fan. After I watched the movie a hundred or so times I decided to explore other books written by Jim Harrison. He is a pretty diverse author and none of his other writings are similar to this book.