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The 9 Best Romantic Comedies of the last 30 years

The 9 best romantic movies from the past three decades

There is nothing wrong with a cheesy romantic film – the emotional rollercoasters, jokes and memorable lines keep you coming back for more. There’s always time to catch up with the best romantic movies you’ve missed and to rewatch the ones you love. If you’re searching for a good romantic film to watch – that is not too corny – we’ve got you covered!

Grab a heavy blanket, pyjamas, and popcorn as I go through a list of some of the best rom-coms made in the past three decades – all so you can spend less time scrolling through Netflix, Amazon Prime, and the rest.

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I’m going to admit I struggled narrowing down some of the best rom-coms I’ve watched, but I knew When Harry Met Sally (1989) would be the first on my list.

Can men and women really be friends?

When Harry Met Sally (1989)

Why? Because this is a classic among the romantic comedies.

To be honest, who doesn’t love a Meg Ryan and Billy Crystal romance?

When Harry Met Sally (1989) tells the story of the relationship of two graduates who carpool together as they move to New York.

After several encounters with fate, a friendship blossoms, and they’re later forced to deal with the dilemma of how they truly feel about each other.

Billy Crystal, actor
Actor Billy Crystal (pictured in 2018). Credit: Gage Skidmore.

The film explores the idea of ‘can men and women ever be friends?’ – mentioned early on by Harry in his belief that attraction will always get in the way.

The idea is simple and we connect to the characters as we watch them mature and develop as they mature from graduates into adulthood.

Harry and Sally know each other well and have friendship, the perfect foundations for a relationship, and despite their polar opposite personalities they get on well – the only thing keeping them apart is their friendship.

The iconic movie includes so many memorable moments including the famous diner scene, which makes me laugh. every. single. time.

The time a ‘boy’ fell in love with a movie star

Notting Hill (1999)

This wouldn’t be a best rom-com list if I didn’t throw in a Hugh Grant movie at least once.

In Notting Hill (1999) we follow the life of a simple bookshop owner William (Hugh Grant) whose life is changed when he meets famous movie star, Anna (Julia Roberts).

Although the plot line may seem far from realistic (but hey it’s entertainment) and at some moments cheesy, I decided to take it for what it is – a simple yet endearing film about two polar opposite worlds colliding.

The ‘who deserves the last brownie scene’ – where as you guessed it – the last brownie is given to the ‘saddest act’ at the dinner table, the honesty and self-deprecating humour displayed in the scene shows the charm of William’s friendship group and thus his world.

Hugh Grant, actor, at Cannes
Actor Hugh Grant (pictured in 1997 at Cannes). Credit: Georges Biard.

Although they may call themselves underachievers, their warmth is ultimately what makes their way of living appealing compared to the isolation and hounds of press that emulates Anna’s world.

William’s small, comfortable – yet very peaceful world – is arguably what draws Anna closer to him.

The scene is so simple and tender (while talking about their downfalls which anyone else would be upsetting), it doesn’t try too hard, and that sets the tone for the rest of the film.

For me, that is what sets the film apart from the rest of the modern romantic movies that try to fit into this structure.

‘No-one puts Baby in the corner’

Dirty Dancing (1987)

Dirty Dancing (1987) is probably one of the most referenced in film history, including memorable lines and the iconic climatic lift scene at the end of the film.

We see the love story of Baby (Jennifer Grey) who is spending her summer at a resort with her family, who falls in love with her dance instructor Johnny (Patrick Swayze).

Swayze’s and Grey’s chemistry is raw and telling to the audience, as it is a fact that both actors didn’t get along on set at first.

This is a tale of forbidden love as Baby, the daughter of a doctor who is staying at the resort, and Johnny who is a hired dancer.

Actor Patrick Swayze
Actor Patrick Swayze (pictured in 1990). Credit: Alan Light.

Johnny wants Baby to tell her dad about their relationship, but she is reluctant, as she can easily be identified as a “daddy’s girl”.

If you dig deeper, this is a story about class and several times throughout the film Johnny backs down to confrontation and is even blamed for a theft.

The idea of class is also depicted through the dance – the upper class (the guests) doing ballroom ‘acceptable’ dance moves and dirty dancing, which is hidden and is a favourite among the lower class.

The rom-com also references the issue of abortion (the movie is set in 1963, when abortion was illegal in America).

Baby, stands up for what she believes in several times throughout the movie. She asks her dad for money for Penny’s abortion and asks him for help when she receives a botched aboriton – and stands up for Johnny – despite the fear of jeopardizing her good relationship with him.

A story about love and loss

Someone Great (2019)

Someone Great (2019) is not your traditional romantic film, so if you’re looking for something cheesy and happy, I would skip this one.

Someone Great (2019) really tugs at your heart-strings as it follows Jenny’s (Gina Rodriguez) break up with her long-term partner Nate Davis (LaKeith Stanfield) before Jenny moves across the country for her new job.

There are various flashbacks of Nate’s and Gina’s relationship, including pivotal milestones, which draws you in and you build a connection.

Gina Rodriguez, actor (pictured in 2013). Credit: Cristian Lazzari/MDC.

You experience the highs and lows, reflecting the devastation of heartbreak, which at least everyone can relate to.

Rodriguez and Stanfield’s chemistry is strong and shows the emotional turmoil you feel in the anticipation of a break-up.

The film’s direction to target an area so relatable and heart wrenching to the everyday watcher cripples them with sadness.

The perfect teenage angst love story

10 Things I Hate About You (1999)

10 Things I Hate About You (1999) is a teen romantic film that walked so 00s teen flicks could run.

Other than Clueless (1995), this is one of my favourite 90s films.

We follow Kat Stratford (Julia Stiles), a high school senior with a spunky and sarcastic attitude and her sister Bianca (Larisa Oleynik).

Bianca can’t go out on a date until her older sister dates, and so a plan is hatched to get Kat to date bad boy Patrick (Heath Ledger).

Heath Ledger alone is enough to make anyone enjoy this movie inspired by Shakespeare’s Taming of the Shrew.

The rom-com still is relevant today, if you take a look at Kat’s character, a strong female and feminist, who is not looking for approval – she knows she doesn’t need Patrick and is aware of her intelligence.

She is often framed by other characters as a ‘bitch’ because of her stand-offish nature, but this is what makes her character stand alone compared to other romantic comedy movies.

If you take Cher (Alicia Silverstone) from Clueless, she shrivels up inside and loses confidence when she thinks Josh doesn’t like her back, her self-worth is completely in the hands of a boy.

Not to say Cher isn’t a great character who delivers many iconic lines (as if’)! But I fell in love with Kat’s character because she is different, coming into the 2000s, when the movie was released, she marks a different kind of woman that girls at high school could become.

Have you ever been stuck in the friendzone?

Just Friends (2005)

Just Friends (2005) follows Chris Brander (Ryan Reynolds) who must face his old high school crush, Jamie (Amy Smart), whose rejection turned him into a bachelor and womanizer.

This is a love story about revenge and you may be able to guess – they become more than friends. I like this film because I take it for what it is, a spoofy and feel-good romantic film, that is an easy watch – and sometimes that is all you want out of a romantic film.

If you’ve ever been in the friendzone this may bring back some buried memories for you – sorry in advance.

If you’re someone who wants light-hearted and goofy comedic movements with some slapstick humour, I would give this a try.

A rom-com full of charm and British wit

Four Weddings and A Funeral (1994)

Another Hugh Grant movie – who would’ve guessed?

Four Weddings and a Funeral (1994) follows Charles (Grant) in Britain and his friendship group, who always seem to be invited to weddings but are never the bride and groom.

At one wedding Charles meets American charmer, Carrie (Andie MacDowell). For Charles, it is love at first sight and although she likes him their attraction ultimately ends up in a one-off fling and Charles has to consider whether he has found true love.

This is a classic love story about unaligned fate where although Charles and Carrie cross paths several times there are road blocks that stop them from going the distance throughout the rom-com.

As most of the scenes centre around (you guessed it) four weddings and a funeral, we don’t really know much about Charles and Carrie – you don’t know about what they do for a living, or much about their backstory.

Grant portrays Charles as a shy man with an awkward demeanour, often forgetful as he is late to a majority of the weddings he attends.

Carrie is assertive and knows what she wants and at the beginning makes advances because Charles tiptoes around what he wants, even when it comes to building a potential relationship with Carrie.

We’re only told about Charles’ background and reluctance in relationships when he runs into his ex-girlfriend at one of the weddings.

This rom-com throws in many characters throughout the film, some of which you forget their names, and how the other characters know them – just like how it would be at an actual wedding.

Four Weddings and a Funeral (1994) is a delightful and charming film and a modern classic of romantic films.

Not your usual love story

Scott Pilgrim Vs The World (2010)

Scottt Pilgrim vs. The World (2010) is a completely unique type of romance film – from plot line to visuals – which is why it’s on the list.

I feel like this film is like marmite – either you love it or you hate it – because not everyone loves eye-popping visuals inspired by comic books.

But the movie has garnered a cult following.

We follow Scott (Michael Cera), a bassist for a garage-rock band dating a high-schooler until he meets Ramona Flowers (Mary Elizabeth Winstead) who he becomes infatuated with on-site.

But in order to date her he must defeat her army of evil exes.

There are quite a few fight scenes so it can get repetitive, and Scott isn’t a very likeable protagonist, as he cheats on his high-school girlfriend, Knives – but hey, not every single protagonist has to be likeable, sometimes it’s refreshing when you don’t.

Cera’s performance that makes Scott look awkward and cringe marks him as an unlikely hero. Trust me, this is not a bad thing in a world that has been taken over by Marvel and DC films.

The movie is creative and playful and definitely worth a watch.

Friendship, hidden feelings and life’s hurdles

Love, Rosie (2014)

Love, Rosie (2014) we follow Rosie (Lily Collins) and Alex’s (Sam Claflin) friendship from the end of secondary school over the course of several years, as Alex moves to America for school – so think When Harry Met Sally, but the love interests are separated by distance.

Rosie has hidden feelings for Alex, who tries to keep their friendship alive despite life’s challenges thrown at them.

Lily Collins, actor
Lily Collins, actor (pictured in 2013). Credit: Gage Skidmore.

It may be slightly cheesy and cliche, but it’s not so predictable that I turned it off after 15-minutes. It’s a light-hearted watch with some heartfelt moments where we sympathise with Rosie.

Lily Collins’ performance pulls the movie through, as she gives Rosie an awkward persona as she blossoms from the mishaps of adolescence into her own as a single mother.

There you go – what is your favourite romantic comedy of the last three decades? Get in touch on Twitter and let us know!

Credits

Editor & Artwork: Richard Williams

Images:

Billy Crystal by Gage Skidmore under Creative Commons License 3.0

Hugh Grant by Georges Biard under Creative Commons License 3.0

Gina Rodriguez by Cristian Lazzari/MDC under Creative Commons License 2.0

Lily Collins by by Gage Skidmore under Creative Commons License 3.0

Patrick Swayze by Alan Light under Creative Commons License 2.0