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The 8 Best Romantic Comedies of All Time

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Love can be a funny thing. You’re walking on air one day and the next day you’re checking your cell phone every five minutes to see if he texted you back; not exactly the “LOL” kind of funny.   In romantic comedy, on the other hand, love is always a funny thing, and it is always the LOL kind of funny. No matter how hopeless things appear or how much wine gets consumed, we can rest assured that at some point a pop anthem will play and the characters will run into each other’s arms like Kermit and Miss Piggy on the Muppet show.

Ok, so life isn’t always like the movies, but that’s why we have them. Romantic comedies can turn desperation into inspiration, self-pity into self-deprecation, and tears of sadness into tears of joy. For us, that puts them right up there with the greatest epics, most gripping war stories, and true-life dramas ever to play on the silver screen. So, without further ado, here are some of our top recommendations for all who are ready to rom-com.

When Harry Met Sally (1989)

Known primarily for Meg Ryan’s not so kosher performance at Katz’s Kosher Deli in New York, when Harry Met Sally is romantic humor and its finest and most irreverent.  If you haven’t seen the movie you should, if you have already, you’ve probably forgotten most, if not all, of the other scenes by now, but that’s just par for the course.

To refresh your minds, or to enlighten them, “When Harry Met Sally,” the relationship, not the movie, gets off to a rather unpromising beginning. Its 1977 and Harry (Billy Crystal) and Sally (Meg Ryan), are college kids on a road trip from Chicago to New York. When it’s almost right out of the gate, and the two are already squabbling like a married couple, the viewer begins to wonder whether these two are meant to be or to never have met in the first place.

This begs the bigger question, and consequent theme of the movie, of whether or not men and women can be friends without benefits. The question is raised verbally throughout the movie, but it is through the relationship and Harry Met Sally that the true answer is revealed. As for the restaurant scene, that’s just the icing on the cake. I’ll have what she’s having? Yes, please.

Bridget Jones Diary (2001)

“A verbally incontinent spinster who smokes like a chimney, drinks like a fish, and dresses like her mother.” When Bridget (Rene Zellweger) hears herself described in these rather harsh, but not completely inaccurate terms, she decides to begin a diary. The intent is to chronicle her journey towards a healthy weight, a healthy lifestyle and, hopefully, a healthy relationship (preferably with her flirty boss, Daniel Cleaver, played by Hugh Grant). But when she learns of Cleaver’s playboy reputation, she begins to have second thoughts.

The other problem is snarky Mark Darcy, played by Colin Firth, Bridget’s childhood acquaintance. Their opinions of one another are mutually disagreeable.  She thinks he’s a snob, he thinks she’s vulgar. But when they find a common enemy in Cleaver, they become the best of friends. Watch this one for the one-liners alone. It’s true rom-com gold.

Hi-Fidelity (2000)

Think of Hi Fidelity as a movie for Green Day fans who choose “When September Ends” over “American Idiot.” Or a movie for romantic comedy fans who happen to like alternative rock. There is a lot of rock music and a lot of rock trivia, (thanks in part to the Jack Black character, (Barry, self-appointed expert in all matters of musical taste) in this movie, but it really centers around the story of Rob, owner of a used record store, who has just broken up with his latest girlfriend, Laura.

The movie begins with Rob (John Cusack) making a list of the last five girlfriends he’s broken up with. That’s what Rob does best, he breaks up with girls. What else he does well, he’s not sure of, but connecting with a girl permanently certainly isn’t one of them. As narrator, Rob often soliloquizes on his plight – he is stuck in the role of rejected lover and can’t seem to fully appreciate a girl quite as much until she’s gone.

The plot unfolds as Rob tries to find a solution to his problem – or at least to find out why he’s obsessed with dreams about kicking the living daylights out of Laura’s new boyfriend.  Jack Black, as Barry along with his coworker, Dick (Todd Louiso), lend their support, taking him to nightclubs and introducing him to new people. Catherine Zeta-Jones makes a cameo as Rob’s former girlfriend who goes into a little too much detail about why she left him. There’s also an appearance by John’s real-life big sis Joan as Laura’s best friend whose relationship with Rob is strictly platonic.

Trainwreck (2015)

In a world where children grow up believing in Cinderella stories and happily ever after, the words “Monogamy isn’t realistic” seem like harsh words coming from a parent. Yet those are the very words Amy’s father uses to inform Amy (Amy Schumer) and her sister that he is divorcing their mother. Twenty-three years later, these words are Amy’s words to live by. She sleeps with whom she wants, when she wants, and sleeping over is not an option.

There are two problems that Amy faces in the movie: her drinking is one, and the fact she actually has a heart is another. No matter how many bottles she downs, she can’t help but feel a little attraction to the sweet geeky Aaron Connors, played by Bill Hader of SNL fame. Will she adhere to her monogamous ideals or will she be willing to go beyond her comfort zone? Fictional evidence that our parents really do mess us up, Train wreck is a rom-com with a message about adulting.

Knocked Up (2007)

When you think of the words “baby daddy,” Ben Stone doesn’t exactly come to mind. He’s content to spend his days smoking marijuana with his friends in their communal man cave working on their celebrity porn website.  Picking up girls and randomly impregnating them is definitely not on his radar. In fact, none of this would have even happened if he knew how to use a condom correctly.

Let’s backtrack a little. Ben (Seth Rogan) meets Alison (Katherine Heigl) at a nightclub where she is celebrating her promotion to an on-air host of E!. They drink, have sex, and at breakfast, find that they have little in common and go their separate ways. (Ben seems somewhat dismayed).

When Alison learns that she has indeed been knocked up, as the title would imply, she tells Ben the news and he’s into it! He’s thrilled to be a daddy and eager to step up to the plate. But Alison has her doubts. Can this unemployed slacker stop with the gynecological jokes once and for all and take fatherhood seriously? Watch “Knocked Up.” It will make you laugh, it might make you cry, but it will definitely make you happy.

My Best Friend’s Wedding (1997)

Unless you’re already in a solid relationship, no one really wants to attend their best friend’s wedding. It means you’ve lost a friend to be single with, are one step closer to inevitable spinsterhood, and that catching the bouquet is going to be a fight to the finish. But what if your best friend’s the groom, rather than the bride and you should have been the one walking down the aisle? Meow!

That’s what happens when Julianne (Julia Roberts) gets a call from her old college flame Michael (Dermot Mulroney). Julianne dumped Michael in college only to declare him her new bestie. They make a pact that if they were both single at 28, they would marry. When they’re almost 28, and Julianne hears from Michael, she’s expecting a proposal, instead, she gets an invitation. He’s calling to tell her he’s getting married in 3 days to a college junior whose dad just happens to own the White Sox and a cable network empire. Apparently, you can’t save people for later.

Julianne, not happy with the news, makes plans to sabotage the wedding. She soon meets Kimmy Wallace (Cameron Diaz) the ditzy but sweet bride to be and the strategy is simple. Endear herself to Kimmy, play along accordingly, and plot to destroy irrevocably. However, Michael is nobody’s fool and he makes sure Kimmy isn’t going to be made into one. But the ending is one you’ll never see coming.

Forgetting Sarah Marshall (2008)

No one does full frontal nudity quite like Judd Apatow. There are no washboard abs, bulging muscles or anything else bulging for that matter. With Apatow, nudity is vulnerability shown in the most irreverent manner. Such is the case in “Forgetting Sarah Marshall.”

The film begins with Peter Bretter (Jason Segel) standing stark naked in the apartment he shares with his soon to be ex-girlfriend Sarah Marshall (Kristen Bell) just when she breaks the news that she’s leaving him for another man. Not a promising beginning to say the least, but even less promising when you consider that Sarah is a hot babe, and Bretter is a schlub, hence the lack of masculine prowess in the full frontal.

Sarah is the star of a ludicrous version of a CSI drama called “Crime Scene.” Peter is a composer who provides the score for the show. The other man is Aldous, a slithering lothario rock star played brilliantly by Russell Brand. Crushed, Peter seeks escape to a Hawaiian Island, only to find Aldous and Sarah had the same idea. Now forgetting Sarah Marshall is going to mean hooking up with Mila Kunis, the hotel concierge who offers Peter an expensive suite for free, provided that he cleans it himself. Can he manage to forget Sarah once and for all or will Peter fly back home to work on his Dracula puppet comedy rock opera, “A Taste for Love?’ Tune in and find out.

Crazy, Stupid, Love (2011)

When a man asks his wife what she wants for dessert and she answers, “A divorce,” you can’t exactly give her a piece of apple pie and act like you didn’t hear it. That’s not how Cal (Steve Carrell) responds to his wife, Emily (Julianne Moore) and he’s definitely too good-hearted to try.  Cal is devastated as are his children, especially 13-year-old Robbie who, by the way, has a crush on his 17-year-old babysitter.

Looking to drown his sorrows, Cal seeks solace in an uptown bar with an improbable number of good-looking ladies. It is there he meets Jacob (Ryan Gosling) lounge lizard and playah extraordinaire. Overhearing Cal’s woe’s Jacob offers to give Cal some tips on the art of picking up girls. Once Cal acquires the right clothes, it’s just a matter of him acquiring the right moves. Jacob is happy to assist.

Here’s how it goes down in a nutshell. The young Robbie continues to pine for the babysitter only to find his feelings, not surprisingly, unreciprocated. Cal puts Jacob’s advice into practice and manages, unexpectedly, to score the wildly beautiful and sexual Kate (Marisa Tomei).  But most unpredictable of all, Jacob falls in love with Hannah, played by Emma Stone. Crazy? Yes. Stupid? No, as ridiculous as some of the premises seem to be, this movie is an accurate and candid representation of the human condition. Love? This movie is all about it.



Victoria Santalesa

About

A native of Brooklyn, NY, Victoria played guitar in a punk band with her twin sister before moving to LA to seek fame and fortune. She now lives in West Hollywood with her husband, tutors children and writes blogs whenever she can.


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