I'll agree with 
"oh brother where art thou"
I thought I was the only one whom liked that movie.. I have it recorded on my DVR and end up watching every so often. 
For me it tends to only be funny movies that I can watch over and over. Stuff like Office Space, 40 year old virgin, that stupid movie by Mtv about that nerdy guy. Stuff like that. 
Any sort of serious movie I end up getting board with, no matter how good it was. However I can watch the movie "24 hour party people" anytime it's on, simply because of the music.