Must watch Classic Rom-Com Movies

There’s something uniquely cinematic about romantic comedies — something that makes them a natural fit for the movies, and life.

There’s a special chemistry that allows us to believe in the magic of destiny, meet-cutes, happily ever-afters, and all of the agonizing cliches that tend to pop up between the two, that gives storytellers permission to swap the stuff of operas and fables into the reality of life.

Whether or not you’d like to admit it, you’re a human being who is actually pretty keen on love and laughter by nature. 

So, here’s a list of a few rom-com movies you must watch.

Pretty Woman

Is there a rom-com list that doesn’t include this movie? What’s left to say about the 1990 tale of the beautiful, charming sex worker and the Wall Street corporate raider who meet and fall in love?

Originally envisioned as a dark indie drama about the underbelly of Hollywood-hell, this movie put a smile on many faces in its non-traditional manner. 

It’s a one hundred percent Grade A romance in an extremely un-Disneyfied package. 

Every small moment that takes place in the movie is sure to fill your heart will joy. And the ending – oh don’t get me started on that!


The motherless daughter, caring for her father and looking for her prince, is a trope that goes back to fairy tales, but how Alicia Silverstone (lead actress in the movie) and writer-director Amy Heckerling contemporized that narrative is what made this film into an instant classic.

Heckerling and her cast gamely navigate around the weird stuff, with Silverstone and Paul Rudd’s chemistry and care for each other shining through in even the weirdest of moments.

Jerry Maguire

He had her at “hello.”

Despite its memorably demonstrative, over-the-top lines, like “You complete me” and “Show me the money,” this is ultimately a movie about how people really fall in love.

This movie may not seem to fit inside the narrow parameters of a prototypical rom-com, but that’s only because there’s so much happening in this six-course meal of a movie that its romance can sometimes feel like an afterthought. 

The reality of this movie can be seen as an escape or alternative from our own lives.

Say Anything…

You need to watch this movie so you’ll understand what it means when someone holds a ghetto blaster over his head outside the window of the woman he loves.

Like most of the teen romance flicks on this list, Say Anything… doesn’t end in a big show. 

This movie is far too sophisticated for such a middling finale. And it’s too busy diving into the angsty, all-consuming, awkward challenge that is young love, as portrayed by the actor in his attempts to woo his beautiful female counterpart.

Crazy, Stupid, Love.

Crazy, Stupid, Love. is a sweet romantic comedy about good-hearted people. Most successful rom-coms tend to win off the back of their laughs or their feels – this movie achieves both.

An entertaining rom-com with plenty of twists is executed perfectly by a talented cast. Apart from the many crossover plotlines, this movie establishes its soft spot for romantic comedies.

When Harry Met Sally

This movie is in the running for the best rom-com of all time because it is sassy, sultry, snappy, cinematic perfection, thanks to words from Nora Ephron and direction from Rob Reiner

It set the gold standard for all romantic comedies that followed once it was released in 1989.

When Harry Met Sally offers essential truths about courtship and relationships, thus making it arguably the greatest romantic comedy in movie history. 

A must watch for every college student on the planet.

Sleepless in Seattle

Utterly strained, but utterly charming, this quick, silly, funny film is entertainment superfood for anyone who believes in second chances and true love.

The film talks about a widower whose son calls into a radio show in an attempt to find his father a wife. On hearing this by chance (or fate), the lead actress is snapped by a moment of pure electricity, and proceeds to pursue them.

One of the bravest things about the film is that the protagonists don’t meet until over an hour in. Their connection is played out on a deeper level. 

Yet, it is the balance of melancholy and fizzing optimism that underpins every word of Nora Ephron’s gorgeous screenplay.

My Best Friend’s Wedding

It’s the oldest trick in the book: a rom-com leading man or lady realizes too late that they’re in love, then declares their feelings anyway to someone who’s no longer available.

My Best Friend’s Wedding tells the story of food critic Julianne Potter (Julia Roberts), who discovers her bestie Michael (Dermot Mulroney) is marrying rich Chicago college student Kimmy (Cameron Diaz). The revelation sends her into a jealousy-fueled revenge plot to steal Michael back and ruin the wedding.

It’s a bittersweet, modern-love morsel with a good amount of drama that should touch moviegoers’ hearts.

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