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If you like this romcom, watch this older (and probably better) romcom

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The Parent Trap

1998

★★★★

This version of The Parent Trap emphasizes the comedy of remarriage aspect through references to My Favorite Wife.

How to Lose a Guy in 10 Days

2003

★★★½

A witty battle of the sexes with elements of comedies of remarriage, reminiscent of old Hollywood screwballs and sex comedies. 

Palm Springs

2020

★★★★½
Anchorman: The Legend of Ron Burgundy

2004

★★★

A witty newsroom battle of the sexes.

Down with Love

2003

★★★★★

Down With Love is an affectionate parody of 50s/60s sex comedies, specifically Pillow Talk and Lover Come Back (both starring Doris/Rock/Tony) and Sex and the Single Girl. Tony Randall cameos in his final role. 

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When Harry Met Sally...

1989

★★★★½
I Married a Witch

1942

★★★★

I Married a Witch inspired the Bewitched TV show. Bell, Book and Candle is also very similar. 

Cactus Flower

1969

★★★★

Cactus Flower was remade as the inferior Just Go With It.

The Doom Generation

1995

★★★★½

Plot inspired by a plot twist in Something Wild.

The Pirate

1948

★★★½

Gene Kelly’s character, like Errol Flynn’s Robin Hood, is the blueprint followed by the leading men in The Princess Bride, The Pirates of the Caribbean, and Tangled. Gene Kelly’s character in DuBarry Was a Lady a similar character reminiscent of Robin Hood. 

Intolerable Cruelty

2003

★★★

Intolerable Cruelty is inspired by the comedy of remarriage subgenre that The Awful Truth is the pinnacle of. 

The Hudsucker Proxy

1994

★★★½

The Hudsucker Proxy is a pastiche of screwball comedies and the works of Frank Capra, referencing His Girl Friday, Meet John Doe, Mr. Deeds Goes to Town, Mr. Smith Goes to Washington, and It’s a Wonderful Life. There are also similarities to Metropolis, How to Succeed in Business Without Really Trying, and The Sweet Smell of Success

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Kiss Me Kate

1953

★★★½

Based off of The Taming of the Shrew. Other notable adaptations of The Taming of the Shrew include Woman of the Year and Moonlighting’s Atomic Shakespeare.

Love Affair

1939

★★★★

Love Affair was remade the same director, Leo McCarey as An Affair to , which is directly referenced throughout Sleepless in Seattle. 

The Awful Truth

1937

★★★★

Other comedies of remarriage include The Philadelphia Story, My Favorite Wife, The Palm Beach Story, Love Crazy, and their countless remakes. 

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Something Wild

1986

★★★★½

Itself inspired by Bringing Up Baby. Similar ‘80’s movies include Who’s That Girl and After Hours

Ball of Fire

1941

★★★★½
His Girl Friday

1940

★★★★★

A gender bent adaptation of The Front Page. Switching Channels is a direct remake. 

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The Princess Bride

1987

★★★★½

Both films are fairytale deconstructions inspired by Tristan & Isolde, which also inspired Vertigo and Mulan/Aurora’s romance in Once Upon a Time

Trouble in Paradise

1932

★★★★½
It Happened One Night

1934

★★★★½

Inspired countless remakes and the blueprint for romantic comedies such as, Roman Holiday, It’s a Wonderful World, The Philadelphia Story, and Leap Year

Come Live with Me

1941

★★★★

Similar elements include green card marriage, the publishing industry, and a grandmother who helps get the couple together. 

Singin' in the Rain

1952

★★★★★
The Philadelphia Story

1940

★★★★★

Play loosely inspired by Pride & Prejudice, The Taming of the Shrew, and A Midsummer’s Night’s Dream.

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Anora

2024

★★★★½