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MY TOP 5: BEST BREAK UP MOVIES

As Paul Anka once said, breaking up is hard to do.

Sadly, he wasn’t just exaggerating for the sake of a good pop song.

These five movies show us the foibles and the pain of a break up.

How it tears your soul into a million pieces and throws it on the ground. Then it stomps on it a little.

Occasionally, though, there’s hope.

Just a glimmer, no doubt. But a definite hope.

Or at least the knowledge that, one day, you’ll get over it and find someone else.

Either way, life goes on.

Note how none of these are called The Break Up.

THE WAR OF THE ROSES (1989)
Directed by Danny DeVito
Written by Michael Lesson
Based on a novel by Warren Adler

The darkest of the dark romantic comedies, The War Of The Roses shows us how bed a break up can really be. If you ever have a break up like this…well…good luck. That’s all I can say.

Kathleen Turner and Michael Douglas are reunited after Romancing The Stone and Jewel Of The Nile, two pretty decent romantic comedy/adventure flicks. Here, though, they’re falling out of love as hard as they can. They’re a married couple who have decided that they just want out. No more of this horrible marriage. Unfortunately, they both want their palatial estate. Neither of them want to be the first to move out.

Their divorce lawyer (and the narrator) is played by their Stone/Jewel co-star, Danny DeVito. He’s as acerbic as ever as a gold-digger who plays them against each other. He also takes on the role of director this time out and he spends no time at all showing us how far these two awful people will go to get the other to leave the house.

Full of bile and spit, The War Of The Roses is one of the under-appreciated classics of the late 80s. Hilarious, heartbreaking and painful. See it with the one you love. But only if you want to leave them.

ANNIE HALL (1977)
Directed by Woody Allen
Written by Woody Allen/Marshall Brickman

The movie that beat Star Wars out for the Best Picture Oscar pretty much deserved it. Alvy Singer (Woody Allen) is a comedy writer who meets Annie Hall (Diane Keaton) and has no intention of dating her. That is, until he really gets to know her. About 90 post-modern minutes later, we know exactly why Alvy and Annie would never work out. We see scenes from all of his past relationships, some of his post-Annie relationships, his childhood and a fantasy sequence or two (including an animated bit).

I would call Annie Hall Woody’s best film, but that’s a very tough call. It’s his first that’s not completely comedy (although, he would say that Love And Death is not a comedy) and his first to have true depth to its characters. Sure, I love the characters in his early films, but I feel for Alvy and Annie in ways that I never felt for Miles Monroe. It’s a movie that gets better every time you see it, but it’s also at its best when you don’t know what’s coming next. In fact, it’s almost easy to forget what comes next because of its structure, and I love that.

Watch for a lot of cameos, often by folks who weren’t well known yet. The number of them will make you forget your mantra.

Manhattan was definitely a runner up here. The main difference is that its ending is almost hopeful compared to this one.

(500) DAYS OF SUMMER (2009)
Directed by Marc Webb
Written by Scott Neustadter/Michael H Weber

When Tom (Joseph Gordon-Levitt) meets Summer (Zooey Deschanel), the sparks fly immediately. For him, anyway. He immediately thinks that this Smiths listening, Toms wearing hipster chick is the “perfect woman.” The two become friends and she tells him that she’ll never be his girlfriend. Of course, that doesn’t stop them from doing couple things, and that just makes Tom fall harder.

This is one of those movies that you either love or you hate. Its detractors say that it’s too cutsy and far too twee for anyone to take as realistic. To me, it’s about as realistic as all of those 80s teen movies that we all love so much. Sure, it’s over the top and silly…but so is love. Everything is bigger than life. Sometimes it’s so outrageous that we forget that life is going on around us.

What makes me love this movie (besides the amazing performances of the two leads) is how perfectly it captures the entire relationship, from the meet-cute beginning to the morning after the “first time” (I’ll never hear Hall & Oates the same again) to bitter, awful, horrible end. (Yeah. Spoiler. There’s a break up.) The story is told the way we remember things, in short bursts, fragmented and not in chronological order. In fact, we start with the break up and then see how it happened. Then we see how they met. Then we see their first date. Then we see their last meal together. It’s a movie of memory. It’s all exaggerated but, in some strange way, perfectly realistic.

Yes, even the cartoon bird that Joseph dances with. Totally realistic.

I certainly won’t say that this is Annie Hall for the hipster generation…but…well…maybe I will.

ETERNAL SUNSHINE OF THE SPOTLESS MIND (2004)
Directed by Michel Gondry
Written by Michel Gondry/Charlie Kaufman/Pierre Bismuth

What more could you want after a horrible break up than to forget that the relationship ever happened? That’s what Lacuna Corp is here for! Their newly developed process will suck away the entire relationship from your memory. Every trace of the girl who broke your heart will be erased…from existence.

Joel Barish (Jim Carrey) wants that done to him so he can forget Clementine Kruczynski (Kate Winslet). They had the most amazing relationship…until she dumped him. Why did she dump him? Because of her own issues, not his. Maybe he had a few issues, but they weren’t as big as hers, so it was time to let him go.

When he finds out that she went to Lacuna to have him sucked out of her mind, he decides to do the same. Somewhere in the middle of the process, though, he realizes that he loves those memories. Can he stop them as the very groundwork of his memories is pulled out of his mind? Can he hold on to her? Or will he lose her again?

One of the best movies of the 00s, Eternal Sunshine has really just one lesson: no matter how bad the break up, there was happiness at one time. And that should be held onto no matter what. Could the relationship work again? Would it end just as badly if you tried again? Who knows? Sometimes it’s not meant to be tried again. Sometimes, though, it’s worth the risk. There’s only one way to find out. And that could be the greatest adventure.

WHEN HARRY MET SALLY (1989)
Directed by Rob Reiner
Written by Nora Ephron

Is this really a break up movie? I say yes. Harry and Sally got together and broke up so many times, that I fully believe that it counts. Here’s the difference: it ends the way we all want our break ups to end.

Harry (Billy Crystal) is a cynical young man who agrees to drive with Sally (Meg Ryan) to New York City after college graduation. On the way, he they learn to not really like each other. They’re so different that they just could never really get along. Funny thing happens, though. They just keep running into each other in the City. It’s as if fate is telling them something. Something that they just don’t want to heed.

Eventually, they heed it and have a horrible break up. Then they meet again. And break up again. It’s just not going to work is it?

Or is it? When Harry Met Sally is very near the last of the great romantic comedies. Very few of them have managed this sort of feeling or hilarity since. (Four Weddings And A Funeral is about the only one I can think of after. Maybe there are others.) Many will say that it’s just not realistic. That two people can’t be friends, then lovers, then hate each other, then friends again and then, finally, lovers again. I can only hope that those people are wrong.

There’s a theory that When Harry Met Sally is kind of the anti-Annie Hall. I get it. It looks a LOT like a Woody Allen film and even has some scenes that are basically cribbed from The Book Of Allen. But it definitely has its own feel and its own voice. It’s a great film in its own right.

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