Media that has made me cry in the relatively recent past (e.g. college +), from the absurd to the ridiculous to the actually sad:

Movies:
LOTR: Two Towers
Pan's Labyrinth
300 (it's the manipulation of rhetorical strategies)
Twilight: New Moon (when she's depressed and/or shots of the landscape and rain)

TV Miniseries:
Doctor Zhivago (version with Keira Knightley etc)

Music Videos:
Taylor Swift, "Love Story"
Taylor Swift, "You Belong With Me"

Songs:
Tim Buckley, "Song To The Siren"
Sufjan Stevens, "Casimir Pulaski Day" (nooo to anything about cancer!)
Nancy Sinatra, "Bang Bang (My Baby Shot Me Down)"

Novels:
Henry James, Portrait of a Lady
Jacqueline Carey, Kushiel's Mercy
Henry Fielding, Tom Jones

Poems:
Edna St. Vincent Millay, "Dirge Without Music"
D.H. Lawrence, "The Ship of Death"
Eavan Boland, "The Pomegranate"
Randall Jarrell, "Death of the Ball Turret Gunner"

I have to append here that I think something from Robin McKinley's books and definitely the Darkangel books has also made me tear up, though I can't quite remember which one.

Finally, in utmost absurdity, my pomegranate earrings from Coryell Design.

(Yes, I bought something. . . and I'm barely managing not to buy EVERYTHING: http://www.etsy.com/shop/CoryellDesign.)