Jenny Gump, Forrest Gump
Forrest Gump is the kind of movie that makes people cry for reasons that they would have never thought of before. Jenny's death, for one, is probably the second most tear-jerking death in the film (sorry Jenny, Bubba is definitely a more memorable character). However, Forrest's reaction to Jenny's death is really what pulls the tears out.
Love Story is a not-so-well-known film that has a gripping twist at the end that will leave you tearing up. A young middle-class musician falls in love with an older lawyer. Their love is taboo in the beginning, but they end up proving their worth to each other in the end. That is, until Jenny contracts a terminal illness and ends their relationship abruptly (with her death).