The Best and Worst Break up Films

by DionysusPsyche

The Best

1. 500 Days of Summer
   This is one of the films where having an anonymous voiceover doesn't feel out of place. Tom (Joseph Gordon-Levitt) and Summer (Zoey Deschanel) have different ideas about love and dating, but when Summer breaks Tom's heart, he relives the past year in an attempt and find out what went wrong.
   
   Why it's Great
   The film does an excellent job of not making either character "the bad guy." It shows you that both these people are awesome, and their chemistry is just alive. The film is fun, and even when it's sad, it's still really good.
2. Forgetting Sarah Marshall
   Peter (Jason Segel) tries to put his past girlfriend (whom he works with) behind him by going on vacation. Unfortunately, Sarah (Kristin Bell) has picked the same location.
   
   Why it's Great
   Everyone sooner or later has to deal with seeing their ex with someone else, but sometimes it feels like when we try to escape them the most is when we're forced to resolve the person we thought was The One. The often vulgar humor clashing with Pete's morose mood and frequent crying is amusing, but Jason Segel's character being a composer makes it even better, because it makes us remember how awesome we are. Pete gets to put his dream at the forefront, which helps us say goodbye to all the Sarah Marshalls that don't deserve us.
3. High Fidelity
   Based on the book by Nick Hornby, this is John Cusack as his best as Rob Gordon who goes back through all the lists of women (like he would any album) that he's loved and how they've broken his heart.
   
   Why it's Great
   This is the mother of all break up films, which dissects each major relationship resolving why Rob shouldn't get back together with any of them, and how it's actually his fault that he screwed up the only one that could have worked. Plus, Rob yells at his ex, "Charlie! You fucking bitch! Let's work out." A sentiment that I'm sure a few of us are familiar with.
4. Better Off Dead
   Lane Myers (yes, Cusack again) decides to kill himself after his girlfriend, Beth (Amanda Wyss), breaks up with him for stereotypical jerky jock.
   
   Why it's Great
   It shows teenagers lamenting their love lives in prototypical dramatic fashion of saying that life just isn't worth it unless you're with the girl you're obsessing about. The under appreciated actor that plays Booger from Revenge of the Nerds is in it. There are competitive racing scenes. Ridiculously awesome and weird one-liners. Take your pick.
5. Eternal Sunshine of the Spotless Mind
   Joel (Jim Carrey) goes to a specialty brain surgery clinic where he undergoes a procedure to wipe his girlfriend from his mind.
   
   Why it's Great
   My favorite role for Jim Carrey and Kate Winslet, this tells a story in reverse. Erasing the person you love from your mind is a pretty nifty way to get rid of them...until you decide that maybe it was the heat of the anger and you love them, even if you're not together.

The Worst

1. Closer
   Based on a play, this film uncovers the depressing double life of cheating and examining whether or not the person you're with actually loves you.
   
   Why it Sucks
   This film actually might make you feel better about your relationship. It's an interesting story, but it really brings out the worst in human beings which is not what you need right now, especially since you're already probably doubting the past.
2. The Break-Up
   In order to keep their apartment, a couple's (Jennifer Anniston and Vince Vaughn) break up gets worse and worse.
   
   Why it Sucks
   This film pretended to be a comedy so audiences would want to watch us. Yet, it shows us everything we hate about break-ups and then some weird unrealistic terrible additional things this couple does to each other.
3. The Shape of Things
   Quiet, nerdy Adam (Paul Rudd) is entranced by art student with big ideas, Evelyn (Rachel Weisz). Yet their bizarre relationship threatens Adam's friendships with his best friends.
   
   Why it Sucks
   While at times boring and weird, this film actually does not suck. Still, you shouldn't watch it right after a break up. It makes you go back and re-examine your old relationships in a way you should only do long after you've distanced yourself from them.
4. SwingersI have never liked this movie. It magnifies everything I hate about the single life, the single person mentality (especially in the '90's), and the vulnerability that one goes through.
5. Now You Know
   This is about the calling off of an engagement. However, this film is extremely pessimistic about relationships and marriage in general. It was the first film I tried to watch after a break up, and I still can't go back and watch it. It's also not a very good movie.