10. Romeo + Juliet (1996)
The Story: Shakespeares classic tragedy, in which Romeo Montague (Leonardo DiCaprio) and Juliet Capulet (Claire Danes) fall madly in love--but their families are at war.
Saddest Part: That tragic ending, of course, in which both lovers end up dead, victims of their own plotting.
9. Revolutionary Road (2008)
The Story: Wannabe actress April (Kate Winslet) and longshoreman Frank Wheeler (Leonardo DiCaprio) meet at a party and are soon married.
Fast forward 15 years, though, and disappointment (not to mention failed careers) has driven a wedge between the pair.
Saddest Part: It all just goes wrong. Franks offered a promotion at work. April gets pregnant (again).
Then April prepares to perform her own desperate vacuum-assisted abortion
8. Brief Encounter (1945)
The Story: Laura Jesson (Celia Johnson) meets Doctor Alec Harvey (Trevor Howard) at the train station one day and the two fall desperately in love.
The only catch? Theyre both married.
Saddest Part: The pair know that they cannot be together, but the saddest part (aside from returning to their boring marriages) is the fact that theyre robbed of a passionate farewell.
7. Casablanca (1942)
The Story: Exiled American freedom fighter Rick Blaine (Humphrey Bogart) is living in Casablanca when former love Ilsa (Ingrid Bergman) walks into his bar.
After reconciling their differences, they decide to run away together, despite the fact that Ilsa is now with husband Victor Laszlo.
Saddest Part: Rick forces Ilsa to escape Casablanca with her husband, knowing hell never see her again.
6. The Bridges Of Madison County (1995)
The Story: Through letters and photos, we learn of a four-day love affair between Robert Kincaid (Clint Eastwood) and Francesca Johnson (Meryl Streep) in 1965.
Saddest Part: Despite their feelings for one another, Robert and Francesca decide not to elope, and instead go their separate ways.
5. Brokeback Mountain (2005)
The Story: In the 1960s, strangers Ennis Del Mar (Heath Ledger) and Jack Twist (Jake Gyllenhaal) go to work herding sheep in Wyoming.
There, an unexpected love story blooms.
Saddest Part: Victims of their time, Ennis and Jack are unable to enter into a conventional relationship. Instead, they marry women and only meet every couple of years.
4. The Notebook (2004)
The Story: That of the society-rocking love affair between country lad Noah Calhoun (Ryan Gosling) and wealthy heiress Allie Hamilton (Rachel McAdams).
Saddest Part: We learn that the older couple weve seen throughout the film are actually Noah and Allie in their twilight years.
No happy endings for them, then.
3. Blue Valentine (2010)
The Story: In a time-flitting ode to the power of heartbreak, we follow the breakdown of Dean Pereira (Ryan Gosling) and Cindy Hellers (Michelle Williams) marriage--from romantic meetcute to shattering final meltdown.
Saddest Part: The entire film, which depicts the peaks and troughs of this couples meltdown in devastating detail.
That said, the desperate sci-fi-themed motel room sequences are up there as some of the films most heart-wrenching.
2. Love Story (1970)
The Story: Well-off Oliver Barrett IV (Ryan ONeal) meets working class loud-mouth Jennifer Cavalleri (Ali MacGraw) and the two fall desperately in love, much to the chagrin of Barretts parents.
Saddest Part: The films stomach-walloping third act, in which Jennifer contracts a serious illness that could separate these star-crossed lovers forever.
Also, Ali MacGraw is just really, really annoying.
1. Gone With The Wind (1939)
The Story: Scarlett OHara (Vivien Leigh) resists the advances of Rhett Butler (Clark Gable) over numerous years because her heart belongs to married man Ashley (Leslie Howard).
Saddest Part: Its all about wanting what you cant have.
While Ashley turns Scarlett away in favour of his wife, he also admits his passion for her after the war.
And Rhett never gives up on Scarlett--until right at the very end.
Frankly, my dear, I dont give a damn.
