The Break-Up (2006)
The first one's a freebie. While billed and marketed as comedy, it got real- real fast. The reason why this is a heartbreaker is because you simply didn't expect it to get that emotional wrenching. It almost felt like a personal attack when Jennifer Aniston and Vince Vaughn verbally abused each other for a good 10 minutes after a light affair from the film. It was so "hard to watch" (thanks, Tracy Jordan), I can't help but swarm in my seat while reliving my arguments with my exes and compare.
Cast Away (2000)
This one's not as obvious. Solitude is not an easy thing, especially when you're closest pal is some volleyball. The gut wrenching portion of this one is not that he spend the entire time alone, but the one thing that's kept him sane is his wife back home is no longer there for him. Obviously, Chuck Noland is a stronger man than I simply because he somehow moves on gracefully. I, on the other hand, would have probably crawled into the fetal position and sob uncontrollably while cursing the world.
Closer (2004)
Pretty darn brutal. The truth sure hurts. Four very honest, no-holds-bar characters lays down the truth to their so-called significant others in this 2-hour entertaining punching bag adapted from the Tony-nominated play with the same name. After the infidelity of two of the characters, each word out of the everyone's mouths is a like venom- quick, sharp and stings like a mofo. Of course, that only means me thinking to myself "Damn, wished I should've said that."
High Fidelity (2000)
Self evaluation after a relationship is never easy. A lot of "Should I have done this", "Should I have done that" sets in when it all goes up in flames. Leave it to Rob Gordon, our hero, to brave the task of asking his former girlfriends what the hell went wrong. While emotionally touching with an relatively positive conclusion, it's the journey of Rob visiting his exes that triggers the inevitable self doubt and confidence. If there's anything to learned here is that you better surround yourself with a stinkin' good support system- even if they're weirdos.
A Single Man (2009)
The first lines of this film says it best: "For the past eight months waking up actually hurts. The cold realization that I am still here slowly sets in". Truer words cannot be spoken by a man filled with grief and heartbreak- though very different from a break up, the termination of a relationship is still there. Watching George Falconer's supposed last day of living could not feel more alone even when he's surrounded by people is beautiful, but no doubt depressing and reflective.
Of course, there are plenty of others film that would be appropriate for this list, these are simply the five I could think of off the top of my head. I'm curious to read what other films folks would consider. So fair warning, watch at your own risk. Just have a bottle of wine and a box of chocolates nearby.
