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

Intolerable Cruelty
★★★

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

Kiss Me Kate
★★★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.

The Pirate
★★★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
★★★★

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

I Love You Again
★★★

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

Down with Love
★★★★★

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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Come Live with Me
★★★★

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

Pillow Talk
★★★★

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
★★★★

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

Love Affair
★★★★

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

The Hudsucker Proxy
★★★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