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Looking at the Best Romantic Comedies of Each Decade

“The Big Sick” (2017) Cinematography by Brian Burgoyne

Earlier this week, a portion of the internet blew up with controversy (isn’t that always the way with Film Twitter?), one surrounding a certain list. The list in question surrounded the best romantic comedies of all time. Now, you can agree or disagree with inclusions or exclusions on a ranking, but something that irked so many people actually caught my eye. The article seemed to skew shockingly modern, especially considering how long the rom-com genre has existed. So, rather than cursing the dark, I decided to light a candle. In short order, I came up with a list of my own, making sure to include as many decades as possible. Today, I’m sharing that with you!

Below, I’ve listed some of my favorite romantic comedies. What I did, to make this a little unique, was categorize them by decade. That way, you can see not just a wide range of eras, but styles as well. While my list does veer modern, as many of mine do, seeing how few rom-com lists make room for the classics had me making sure I didn’t exclude older titles, especially since something Yours, Mine, and Ours is an all-time favorite. So, obviously enjoy the list, and find a few to watch, but definitely open yourself up to some of the older titles you haven’t seen, not just the newer ones…

Here now are my picks for the best romantic comedies of each decade, going back as far as I was comfortable with:

2020’s

Awesomeness Films

Palm Springs

Spontaneous

The Worst Person in the World

2010’s

‘Long Shot’ (2018) Cinematography by Yves Bélanger

About Time

The Big Sick

Crazy, Stupid, Love.

Long Shot

Love and Other Drugs

Silver Linings Playbook

Sleeping with Other People

Trainwreck

What If

2000’s

Knocked Up

(500) Days of Summer

The 40 Year Old Virgin

Bridget Jones’ Diary

Elizabethtown

Failure to Launch

Forgetting Sarah Marshall

Garden State

The Girl Next Door

High Fidelity

Jersey Girl

Knocked Up

Love Actually

Something’s Gotta Give

Zack and Miri Make a Porno

1990’s

“Chasing Amy” (1997) Cinematography by David Klein

10 Things I Hate About You

As Good As It Gets

Blast From the Past

Chasing Amy

Doc Hollywood

Four Weddings and a Funeral

Groundhog Day

It Could Happen to You

Jerry Maguire

Notting Hill

Pretty Woman

Sleepless in Seattle

There’s Something About Mary

The Wedding Singer

1980’s

Say Anything

Bull Durham

Moonstruck

Peggy Sue Got Married

The Princess Bride

Say Anything

The Secret of My Success

Splash

When Harry Met Sally

1970’s

Annie Hall

Annie Hall

The Goodbye Girl

Harold and Maude

1960’s

Yours, Mine, and Ours

The Apartment

Breakfast at Tiffany’s

Yours, Mine, and Ours

1950’s

“Singin’ in the Rain” (1952) Cinematography by Harold Rosson

Pillow Talk

Roman Holiday

Singin’ in the Rain

Some Like it Hot

1940’s

Philadelphia Story, The (1940) | Pers: Katharine Hepburn, James Stewart | Dir: George Cukor

Adam’s Rib

His Girl Friday

The Philadelphia Story

1930’s

City Lights

Bringing Up Baby

City Lights

It Happened One Night

What are your favorite romantic comedies? Let us know!

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Robert Hamer
5 months ago

I think one of the reasons why that list irked so many people was because that genre is one of the few where skewing exclusively modern is totally inexcusable. The romantic comedy enjoyed its golden age during the 30’s and 40’s, with even its mid-tier classics blowing all but a small handful of romcoms made in the last fifty years out of the water.

Many of the most complex, densely-structured thrillers of the 21st century lauded by Film Twitter are nowhere near as clever or well-written as The Lady Eve.

Kellie
Kellie
5 months ago

This isn’t a complete list but it’s decent one.

1930’s
City Lights
My Man Godfrey
Bringing up Baby
Ninotchka

1940’s
The Philadelphia Story
The More the Merrier
Talk of the Town

1950’s
Born Yesterday
Gentlemen Prefer Blondes
How To Merry A Millionaire
Sabrina
The Solid Gold Cadillac
Some Like It Hot
Bell , Book and Candle
Lady and The Tramp

1960’s
The Apartment
Father Goose
Prudence and the Pill

1970’s
What’s up Doc
High Anxiety

1980’s
Victor/ Victoria
The Princess Bride
Moonstruck
Baby Boom

1990’s
Emma
Shakespeare In Love

2000’s
Chocolat
Amelie
Down With Love
View From The Top
No Reservations
A Good Year
Julie and Julia

2010’’s
Beginners
Frances Ha

The 2010’s and 2020’s lacking I either haven’t watched enough or liked enough of the genre . I hope to catch up . I tried not to overlap too much and stay with mostly romantic comedies.

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