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

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There are 130 films in this list available on Amazon Video US.

Intolerable Cruelty

2003

★★★

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

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.

Teen Beach Movie

2013

Teen Beach Movie satirized the teen beach comedy genre invented by Gidget.

Anchorman: The Legend of Ron Burgundy

2004

★★★

A witty newsroom battle of the sexes.

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. 

I Married a Witch

1942

★★★★

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

I Love You Again

1940

★★★

Both romantic comedies feature chaotic couples falling in love again after cases of amnesia. 

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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Pillow Talk

1959

★★★★

Besides the aforementioned, similar movies include Send Me No Flowers, Move Over Darling, That Touch of Mink, and Man’s Favorite Sport.

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Cactus Flower

1969

★★★★

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

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 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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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. 

The Parent Trap

1998

★★★★

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

The Doom Generation

1995

★★★★½

Plot inspired by a plot twist in Something Wild.