Best Break-Up Movies of All Times

The days leading up to Valentine’s Day inspire many people to cuddle up with their sweethearts and watch romantic films. But what about single people, or worse, people who have just had their heart broken by an unexpected or nasty breakup? Don’t despair. Buy yourself some chocolate and ice cream, have yourself a good cry and curl up in front of your TV to embrace your newfound freedom. Here are eight great break-up movies that will make you feel glad to be single.
1. Sleeping With the Enemy (1991)
Think twice about envying the woman who appears to have it all: a handsome husband, a nice house and basically anything that money can buy. So what would bring such a charmed housewife (Julia Roberts) to fake her own death, cut off her hair, move across the county and change her name? Why, her rich husband of course! See why this thriller will make you glad that you never got married or glad to be divorced.
2. The War of the Roses (1989)
In another (seemingly) perfect marriage, the Roses are a professional, middle-aged couple who live in a small mansion and have two kids in college. They grow tired of each other, and their bitterness turns into a contest to out-humiliate each other in front of each other’s clients and friends. Eventually, their quarrels escalate into a violent personal war inside their large house where they both end up dead under the chandelier. This version of War of the Roses makes the real battles between the Houses of York and Lancaster at the end of the Middle Ages seem like child’s play.
3. Thelma and Louise (1991)
Geena Davis and Susan Surandon star in this action-packed story of two best friends who decide to go on a girls’ weekend trip. They end up being the victims of circumstance and become outlaws on the run. The men in their lives are enough to make any woman happy to die alone. If those weren’t enough reasons to convince you, the movie is worth it just to see a young Brad Pitt make an appearance before he became famous.
4. Secretary (2002)
This is a good movie to watch if you have ever thought your own life was messed up. A socially awkward and dysfunctional young female who just checked out of the hospital for self-injury starts dating her boss, who introduces her to a relationship of BDSM. Since she already has a self-destructive streak, she falls in love. Her boss fires her, humiliates her and eventually marries her so that they can continue their dominant/submissive lifestyle happily ever after.
5. Closer (2004)
This mixed-up tangle of love stars Julia Roberts, Natalie Portman, Jude Law and Clive Owen. Basically, four people’s lives are intertwined by lust. No one is really happy with the person he or she is with. When their eyes wander, they switch partners and each end up more heartbroken than they were in the beginning. This is a good movie to watch if you feel that your quest for a satisfying relationship is thwarted by the very confusing and insatiable human condition.
6. Heavenly Creatures (1994)
Set in the 1950s, this is a story of two women who befriend each other and have a relationship that borders on lesbianism (considered a mental illness at the time). This tale of an obsessive relationship between two girls ends with murder by brick bludgeoning. If you think you have problems with your own love life, try living in the old days where you considered mentally ill if you did not conform to society’s standards.
7. Sid and Nancy (1986)
Nothing makes you happier to be single than a good, old fashioned dysfunctional rocker love story. This movie is based on the true story of Sid Vicious (Gary Oldman), bassist of the seminal punk rock band The Sex Pistols and his girlfriend, Nancy Spungen (Chloe Webb). Filled with an abundance of reckless drugs and sex, the love story ends up with a stabbing. On an interesting side note: Courtney Love auditioned for the role of Nancy Spungen but did not get it. Ironically, she was later compared to the rock star’s troubled girlfriend on account of her marriage to Kurt Cobain.
8. Revolutionary Road (2008)
Have you ever dreamed of getting married and starting a family? Maybe you’ll decide that traveling the world and pursuing your dreams should come first after you see this depressing movie. A young couple falls in love, moves to the suburbs, starts a family and becomes completely miserable as the bored housewife experiences a midlife crisis. She plots to move the family to France to pursue acting but a pregnancy with the couple’s third child puts the couple in disagreement and as a result, the desperate housewife gives herself an abortion and dies. Leonardo DiCaprio and Kate Winslet costar in this drama that makes their last film together, The Titanic, look like a love story with a happy ending.
Now you have plenty to keep you occupied, with eight Valentine’s Day movies for the jilted, single or heartbroken who are looking for movies to make them feel better. Single life does not seem so bad now, does it?
April Lentini writes for Greektown Chicago Apartment Guide
Image: ginnerobot (flickr)