Entertainment Movies Our list of the 25 greatest rom-coms of all time
Updated:

Our list of the 25 greatest rom-coms of all time

AAP
Share
Twitter Facebook Reddit Pinterest Email

It’s been 25 years since When Harry Met Sally charmed cinema-goers. Since then, the rom-com has slowly lost its spark.

Hollywood screenwriters, like Nora Ephron who single-handedly reinvented the genre with her When Harry Met Sally screenplay, mastered the art of the romantic comedy with a delicious mix of a fast-paced and funny plot-lines, with pull-at-your-heart-strings desire between the protagonist and, usually her, love interest.   

· WATCH: the film inspiring many to rethink their lives
· Our coolest winter films – what’s your favourite?

While the modern heyday of movie treasures like Meg Ryan, Tom Hanks, John Cusack and Julia Roberts in the late 1980s and 1990s provided a seamingly endless stream of light hearted but sassy movies, the dawn of a new millennium saw the quality dissipate – rather rapidly.

Despite valiant efforts from Bridget Jones and several Kate Hudson flicks, gaudy Adam Sandler movies and the inexplicable rise of Katherine Heigl firmly stomped on any hopes for a rom-com rebirth.

Is there any hope for the film category? There’s certainly a lot in the back catalogue.

Here are The New Daily’s top 25 romantic comedies of all time:

1940 – The Philadelphia Story

Cary Grant and Katherine Hepburn. Photo: AAP
The Philadelphia Story: Cary Grant and Katherine Hepburn. Photo: AAP

The original screwball comedy of remarriage. Pairing Katherine Hepburn with Cary Grant and James Stewart means this fabulous film still has as much oomph as when it was released almost 75 years ago.

1959 – Some Like It Hot

Some Like It Hot: Marilyn Monroe and Tony Curtis. Photo: AAP
Some Like It Hot: Marilyn Monroe and Tony Curtis. Photo: AAP

Many romantic comedies from 1950s and 1960s have not stood the test of time but this classic, with the sizzling Marilyn Monroe and Tony Curtis, is legendary.

1977 – Annie Hall

Annie Hall: Diane Keaton and Woody Allen. Photo: AAP
Annie Hall: Diane Keaton and Woody Allen. Photo: AAP

Woody Allen’s masterpiece makes both the list for romantic comedies and just plain comedies. It may end on a bittersweet note but this telling of the death a romance is exquisite.

1977 – The Goodbye Girl

The Goodbye Girl: Marsha Mason and Richard Dreyfus. Photo: AAP
The Goodbye Girl: Marsha Mason and Richard Dreyfus. Photo: AAP

This gorgeous 1970s rom-com with Richard Dreyfus and Marsha Mason was written by US playwright Neil Simon. Mason plays the unlucky in love single mum who takes in a precocious, but ultimately loveable, roommate.

1984 – Sixteen Candles

Sixteen Candles: Michael XXXX, Anthony Michael Hall and Molly Ringwald. Photo: AAP
Sixteen Candles: Michael Schoeffling, Anthony Michael Hall and Molly Ringwald. Photo: AAP

You might be wondering where Molly Ringwald’s Pretty in Pink fits into this list. It doesn’t. Sixteen Candles trumps it every time.

1989 – When Harry Met Sally

When Harry Met Sally: Meg  Ryan and Billy Crystal. Photo: AAP
When Harry Met Sally: Meg Ryan and Billy Crystal. Photo: AAP

Screenwriter Nora Ephron reinvigorated the genre with this blockbuster. Director Rob Reiner casting Meg Ryan and Billy Crystal as the friends who have a love-hate relationship secured its success.

1989 – Say Anything

Say Anything: John Cusack and Ione Skye. Photo: AAP
Say Anything: John Cusack and Ione Skye. Photo: AAP

The teen couple, magically portrayed by John Cusack and Ione Skye, steam up every scene of this Cameron Crowe 1980s picture.

1990 – Pretty Woman

Pretty Woman: Julia Roberts and Richard Gere. Photo: AAP
Pretty Woman: Julia Roberts and Richard Gere. Photo: AAP

As well as catapulting Julia Roberts to superstardom, Pretty Woman hit the jackpot with a plot that sees a beautiful hooker swept off her feet by a handsome, rich lawyer – well played, Richard Gere.

1992 – Strictly Ballroom

Strictly Ballroom: Paul Mercurio and Tara Morice. Photo: AAP
Strictly Ballroom: Paul Mercurio and Tara Morice. Photo: AAP

Probably the most successful Australian rom-com ever made, Baz Lurhmann’s Strictly Ballroom is as fun today as it was when it opened in the Un Certain Regard category at Cannes in 1992.

1993 – Sleepless in Seattle

Sleepless in Seattle: Meg Ryan, Ross Malinger and Tom Hanks. Photo: AAP
Sleepless in Seattle: Meg Ryan, Ross Malinger and Tom Hanks. Photo: AAP

The teaming of Tom Hanks and Meg Ryan, who was undoubtedly the Queen of the genre in the 1990s, made this super sweet film a worldwide phenomenon.

1994 – Four Weddings and a Funeral

Four Weddings and a Funeral. Photo: AAP
Four Weddings and a Funeral. Photo: AAP

Everything about this Richard Curtis-written iconic film works, even if you don’t like Hugh Grant or Andie MacDowell. We especially love watching the romantic leads stumble along with other lovers before finally falling into each other’s arms.

1994 – Muriel’s Wedding

Muriel's Wedding: toni Collette. Photo: AAP
Muriel’s Wedding: Toni Collette. Photo: AAP

Another Australian treasure, Muriel’s Wedding is the hilarious story of a wedding-obsessed woman who wins in life despite the odds being stacked against her.

1994 – Reality Bites

Reality Bites: Ethan Hawke and Winona Ryder. Photo: AAP
Reality Bites: Ethan Hawke and Winona Ryder. Photo: AAP

This one might catch you off guard as a romantic comedy, but the Ben Stiller directed Reality Bites is really just the story of a boy and girl who struggle to get it together. It’s very funny and by the end of the film you are desperate for Ethan Hawke and Winona Ryder to work it out.

1995 – While you were Sleeping

While You Were Sleeping: Sandra Bullock and Bill Pullman. Photo: AAP
While You Were Sleeping: Sandra Bullock and Bill Pullman. Photo: AAP

Following on from the success of Speed, Sandra Bullock seemlessly moved into romantic comedies as the girl next door, taking over from Meg Ryan. Here she falls in love with a man in a coma and tells his family she is his fiance.

1997 – My Best Friend’s Wedding

My Best Friend's Wedding: Cameron Diaz, Dermut Mulrony and Julia Roberts. Photo: AAP
My Best Friend’s Wedding: Cameron Diaz, Dermot Mulroney and Julia Roberts. Photo: AAP

At the height of her fame, Julia Roberts was the unlucky in love beauty who tried to win her best friend’s heart on the eve of his wedding to another woman.

1999 – 10 Things I Hate About You

10 Things I Hate About You: Heath Ledger, Allison Janney and Julia Stiles. Photo: AAP
10 Things I Hate About You: Heath Ledger, Allison Janney and Julia Stiles. Photo: AAP

Based on Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You straddles teen flick and rom-com perfectly. Heath Ledger also became a huge star on the back of its success.

1999 – Notting Hill

Notting Hill: Julia Roberts and Hugh Grant. Photo: AAP
Notting Hill: Julia Roberts and Hugh Grant. Photo: AAP

The movie star and the fop. Notting Hill had the irresistible combination of unattainable beauty, the hapless man in love, and an excruciating housemate who accidentally threatens to ruin it all.

1999 – Never Been Kissed

neverbeenkissed
Never Been Kissed: Drew Barrymore and Michael Vartan. Photo: AAP

Drew Barrymore has starred in plenty of romantic films but none stand up as well as Never Been Kissed. She portrays the dorky lead so well you can hardly believe she will ever get the guy.

2000 – High Fidelity

High Fidelity: Iben Hjejle and John Cusack. Photo: AAP
High Fidelity: Iben Hjejle and John Cusack. Photo: AAP

Another John Cusack vehicle, there’s more to come … Based on Nick Hornby’s best-selling novel, High Fidelity takes the view of the man who has lost the love of his life and traverses his own romantic history to figure out what went wrong.

2001 – Bridget Jones’s Diary

Bridget Jones's Diary: Renee Zelleweger. Photo: AAP
Bridget Jones’s Diary: Renee Zellweger. Photo: AAP

Everywoman Bridget Jones plays out our own fears and fantasies in this female-favourite film. Based on Jane Austen’s Pride and Prejudice, Bridget Jones’s Diary is the quintessential chick flick.

2001 – Serendipity

Serendipity: Kate Beckinsale and John Cusack. Photo: AAP
Serendipity: Kate Beckinsale and John Cusack. Photo: AAP

This John Cusack-Kate Beckinsale movie is all about a star-gazing couple who never seem to be in same place at the same time.

2002 – Sweet Home Alabama

Sweet Home Alabama: Reese Witherspoon and Patrick Dempsey. Photo: AAP
Sweet Home Alabama: Reese Witherspoon and Patrick Dempsey. Photo: AAP

Reese Witherspoon is the city slicker who returns home to Alabama to divorce her first husband. Instead she is swept back up in the town where she spent her youth.

2006 – The Holiday

The Holiday: Kate Winslet and Jack Black. Photo: AAP
The Holiday: Kate Winslet and Jack Black. Photo: AAP

Using the tried and tested formula of the slow-burn love story, The Holiday has an all-star cast and often gets criticised for being too schmaltzy, but it’s still beloved.

2007 – Waitress

Swaitress: Nathan Fillion and Keri Russell. Photo: AAP
Waitress: Nathan Fillion and Keri Russell. Photo: AAP

A cute and quirky indie romance, Waitress gathered a cult following after its release. Keri Russell is the struggling pregnant waitress who can cook a mean pie, while still managing to fend off every man in town.

2013 – Enough Said

Enough Said: James Gandolfini and Julia Louis-Dreyfus. Photo: AAP
Enough Said: James Gandolfini and Julia Louis-Dreyfus. Photo: AAP

James Gandolfini’s penultimate role saw him unusually cast as the romantic lead opposite Julia Louis-Drefus in a story of a second chance at love.

What’s your favourite romantic comedy? Tell us below.

With Susannah Guthrie

Comments
View Comments