Here at Romance.com.au we LOVE romantic comedy movies. And we love lists. Now that we’ve entered a brand-new decade we thought we’d pick our favourite rom-com from every decade (from 1950-today).

Let the games begin!

via GIPHY

*Us, trying to pick just one movie from every decade*

1950’s: Singing In The Rain

The 1950’s was an iconic decade for romantic comedy- with timeless classics like Roman Holiday, Some Like It Hot and To Catch A Thief. Basically every movie starred Audrey Hepburn, Marilyn Monroe, Frank Sinatra, Grace Kelly or Cary Grant. Most had musical numbers. But undoubtedly the most icnoic film from that decade is 1952’s Singing In The Rain.

Starring Gene Kelly, Debbie Reynolds & Donald O’Connor, this film follows the careers (and romance) between Don Lockwood and Kathy Seldon, as they face a Hollywood inexorably changed by the introduction of sound to movies (or ‘talkies’). It’s hilarious (the ‘Make ‘Em Laugh’ dance sequence alone is side splittingly hilarious), gorgeous on screen (this period of history marked the transition from black and white to colour film and the studios were GOING FOR IT with lavish use of colour on screen) and utterly romantic. Oh and it has 100% on Rotten Tomatoes.

1960’s: Breakfast At Tiffany’s

Audrey Hepburn IS the face of 1960’s romantic comedy. From Charade to How To Steal A Million and My Fair Lady she was in so many of the decade’s most memorable films. Although we should give a special shoutout to fellow actresses Doris Day, Barbera Streisand (Hello Dolly is a particular favourite of mine) and Shirley McLane, Audrey takes the cake. Or rather, coffee, standing outside a Tiffany’s store.

Breakfast at Tiffany’s follows a struggling writer, who moves to New York and falls desperately in love with Holly Golightly, his eccentric socialite neighbour. The film is famous for THAT black dress, Audrey Hepburn singing ‘Moon River’ and the gorgeous soundtrack by Henry Mancini. Yes, it’s not a perfect film (see: Mickey Rooney), but it’s the stand out of the decade, and a film still watched even in 2021.

1970’s: Grease

Grease is the word. Do I need to justify this one?

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1980’s: When Harry Met Sally

Although the 1980’s has a special place in my heart for the true birth of the teen rom com (Pretty In Pink, Can’t Buy Me Love, Sixteen Candles, Mystic Pizza, Some Kind Of Wonderful) the best rom-com of the decade truly has to be When Harry Met Sally. A chance encounter between two graduates culminates in a short-term friendship. But when fate brings them back together five years later, they are forced to deal with how they feel about each other. Charming, witty, endlessly quotable and critically acclaimed. When Harry Met Sally is one of the most re-watchable romantic comedy films of all time.

“I’ll have what she’s having.” indeed.

1990’s: Pretty Woman & Notting Hill

“I’m just a girl, standing in front of a boy, asking him to love her.”

The 1960’s had Audrey, the 1980’s had Meg, so did the 1990’s have Julia. Pretty Woman and Notting Hill are two of the biggest romantic comedies of all time, starring one of the biggest stars of all time. They’re cemented as romantic comedy classics. To quote Vivian herself, to pick any other rom-com would be a ‘”Big Mistake. Big. Huge.”.

2000’s: Love Actually

A Christmas themed romantic comedy following an ensemble of Londonsiders in the month before Christmas as they navigate various kinds of romantic relationships. It’s not perfect. But if you don’t tear up every time you watch the sequence at the arrivals gate at Heathrow, cheer when Sam finally gets to tell his crush he likes her at the boarding gate, or seethe with rage when Emma Thompson’s Karen discovers her husband’s infidelity you have a heart of stone.

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2010’s: To All The Boys I’ve Loved Before

Perhaps a controversial choice (this is the decade that brought us Ryan Gosling and Emma Stone in BOTH Crazy, Stupid Love and La La Land), but the 2010’s was a HUGE decade for streaming platforms, and particularly Netflix original movies. To All The Boys was a PHENOMENON when it came out, and honestly it holds up to a re-watch (even if the sequels were a tad disappointing). The film follows Lara Jean, a teen whose life is forever altered when her secret love letters are exposed, and is utterly delightful.

…the future

2021: In The Heights

This movie musical is set for release THIS MONTH. Based on a musical by Lin Manual Miranda (think Hamilton) the musical follows the lives and romances of a Washington Heights community over the course of a few summer days. At the intersection of it all is a likable and magnetic bodega owner who hopes, imagines and sings about a better life.

Watch the trailer below:

Do you agree with our list?

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