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50. The Fly (1986)
Saddest Part: Seths slow transformation into a fly after a Telepod test goes wrong dooms his relationship with Veronica
49. Annie Hall (1977)
The Story: Alvy Singer (Woody Allen) looks back over the past year and attempts to figure out just why his relationship with Annie Hall (Diane Keaton) ended.
Saddest Part: Its about a relationship we already know comes to an end.
That, and watching Alvy doing everything wrong is often painful to watch. (In the best way.)
48. Cruel Intentions (1999)
The Story: Sebastian (Ryan Phillippe) pursues innocent Annette (Reese Witherspoon) as part of a bet with his seductive step-sister Kathryn (Sarah Michelle Gellar).
It isnt long, though, before he starts having real feelings for Annette.
Saddest Part: The films emotional final act, which has Annette turning her back on Sebastian only for him to get run over and killed
47. A Single Man (2009)
The Story: English professor George (Colin Firth) is grieving the death of his lover Jim (Matthew Goode), something he decides is impossible to overcome.
Saddest Part: George determines to kill himself.
Except just as he starts to rediscover the beauty in life (in no small part thanks to Nicholas Hoults Kenny) and rethink his suicide, he has a heart attack and dies. Typical.
46. Sleepless In Seattle (1993)
The Story: Annie Reed (Meg Ryan) is engaged to Walter (Bill Pullman) when she hears the sad story of Sam Baldwin (Tom Hanks) over the radio.
Hes just lost his wife, and his son (somewhat outrageously) wants to help him find a new wife.
Saddest Part: It all comes alright in the end (mostly), but before that its hella depressing as Sam grieves over the loss of his wife.
Also, what about poor Walter?
45. Big Fish (2003)
The Story: During his travels, Edward (Ewan McGregor) meets Sandra Templeton (Alison Lohman).
When he loses track of her (something about time standing still), circus-owner Amos (Danny DeVito) promises to tell Edward one thing about her every year so he can eventually find her.
Saddest Part: It takes Edward so long to learn enough about Sandra to track her down that when he finally finds her shes already engaged.
Alright, so its happy (just about) in the end, but those years of waiting must have been seriously depressing.
44. An Affair To Remember (1957)
The Story: Nickie Ferrante (Cary Grant) and Terry McKay (Deborah Kerr) meet on a cruise ship and have an affair despite both being engaged.
They agree to meet again in six months time at the top of the Empire State Building--so long as theyve ended their respective relationships.
Saddest Part: Terry doesnt turn up for the meet at the Empire State Building.
Nickie only discovers the reason why when he eventually meets her--and discovers shes now wheelchair-bound. If you can paint, I can walk; anything is possible, don't you think? says Terry.
43. The Painted Veil (2006)
The Story: Trapped in a marriage of convenience, Kitty (Naomi Watts) meets Charlie Townsend (Liev Schreiber) and has an affair with him.
Which, understandably, puts her marriage somewhat on the rocks.
Saddest Part: Furious at her infidelity, Kittys husband Walter (Edward Norton) forces her to move to a remote part of China where he will be working.
After a time, their marriage improves, but then Walter contracts cholera and dies
42. Onegin (1999)
The Story: Eugene Onegin (Ralph Fiennes) catches the eye of young socialite Tatyana (Liv Tyler), who professes her love for him.
Uninterested, though, Onegin merely ignores her advances.
Saddest Part: Years later, Onegin meets Tatyana again, and makes it his mission to win her hand.
However, Tatyana is now married, and has no intention of cheating on her husband.
41. Steel Magnolias (1989)
The Story: Shelby (Julia Roberts) and Jackson (Dylan McDermott) get married and are all ready for their happily ever after.
Except Shelby has type one diabetes, which means if she ever gets pregnant she could fall seriously ill.
Saddest Part: After successfully giving birth to a baby boy, Shelby suffers kidney failure.
Her body rejects a transplant and she falls into a coma, then dies.
