I haven't watched this in years, but I cry pretty much straight through Radio Flyer. Similarly, I haven't seen A River Runs Through It in a long time, but I recall it resulting in a pretty good cry.

As for books, Bridge to Terabithia (I refused to watch the movie because it would make me too sad) and Where The Red Fern Grows both still haunt me as beautifully heart-wrenching stories even though I read them around the age of 9.