The Very Best of Problematic 1960s Rom-Coms with Great Style and/or Cast Chemistry
These films defined my young teenagedom.
They taught me valuable lessons about toxic masculinity and the patriarchy sitting around laughing while snatching women's autonomy.
When I say problematic, I mean truly troubling: regressive values, cultural appropriation, stereotypes, horrifying plot points.
They also can be super stylish and fun surviving on pure charisma and fashion and chemistry.
BUT VIEWER BEWARE!
This list is for a very specific kind of 1960s rom-coms, so you will see omissions of actual excellent, excellent films (BAREFOOT IN THE PARK or HOW TO STEAL A MILLION or FOR LOVE OF IVY) because they do not fit the criteria of horrifically troubling, but still somehow watchable.
In order by release date.
Rally ‘Round the Flag, Boys! (1958)
Troubling: A WHOLE LOT. I haven’t actually watched this in a while, but I am certain there is some heavy-duty cultural appropriation in some of the fantasy sequences.
Fun: Joanne + Paul is always a must watch for pure delightful chemistry. <3
Pillow Talk (1959)
Troubling: whole lotta sexist gender stereotypes; distressing “kidnapping” scene.
Fun: Doris Day is the queen of the problematic rom-com, and she drags us through them with sheer force of personality and spirit and Rock Hudson is her wonderful friendly match! THIS. IS. THE. PROTOTYPE.
Come September (1961)
Troubling: I mean, it’s 1961 views of gender roles, but it’s not really the worst tbh.
Fun: Honestly, at least the men are forced to change, adapt, and grow. That’s a rare sight in a 1960s comedy. Rock Hudson at his funniest. Gina Lollobrigida so funny and stunning. Sandra Dee + Bobby Darin absolutely the cutest. Plus stunning Italian views! Fashion! Bobby Darin singing!
The Notorious Landlady (1962)
Troubling: Yes, there is some questionable slapstick if memory serves (need to rewatch this one).
Fun: Kim Novak is so cool and mysterious and fun and ahhh! Jack Lemmon is the purest delight and Fred Astaire is a stylish bystander.
Boys’ Night Out (1962)
Troubling: An absolute nightmare of regressive messaging and misogynistic characters. Truly it boggles the mind.
Fun: But Kim Novak is genuinely iconic here and James Garner is charming to a scary degree, and together they have wildly perfect, charismatic chemistry.
If A Man Answers (1962)
Troubling: Men are terrifying is the conclusion this film makes while intending the opposite.
Fun: SANDY + BOBBY MAKES MY HEART SOAR! They are so, so, so, so, so cute! Give them everything! EVERYTHING!
The Thrill of It All! (1963)
Troubling: MAN IS MAD THAT HIS WIFE IS SUCCESSFUL.
Fun: The two empires of 1960s romcoms united at last—Doris Day + James Garner. The power they had. Some absolutely absurdly fun 1960s consumer lifestyle moments. An entire swimming pool full of bubbles! James Garner drunk acting! Garner had this high praise for the film: “Better than it should have been… because of Doris.”
A New Kind of Love (1963)
Troubling: Probably. I haven’t watch this one in years. I will rewatch and update here.
Fun: FASHION. FASHION. FASHION. Plus Joanne Woodward being cool and Paul Newman unable to look away.
Sunday in New York (1963)
Troubling: Bro needs to stay out of his sister’s sex life. It’s really too much.
Fun: Jane Fonda is literal sunshine, and this movie just makes you want to walk around a city on a perfect fall/spring day and have adventures.
The Wheeler Dealers (1963)
Troubling: I mean, the characters hate women, but that is supposed to be absurd even in the movie, but also the movie is sorta like, “Well thems the breaks ya know.”
Fun: Lee Remick is a goddess. James Garner is perfectly cast as a Yale boy pretending to be a sweet ol’ Texas boy to con people out of money.
Move Over Darling (1963)
Troubling: ehhhhhh.
Fun: Doris Day + James Garner unite for a remake of My Favorite Wife and they have a great time and so do we!
Send Me No Flowers (1964)
Troubling: Can’t remember a troubling moment (that in itself may be troubling).
Fun: Rock Hudson’s absolute funniest performance of all time. Literal iconic work.
You Must be Joking! (1965)
Troubling: I think there are some ~problematic~ gags.
Fun: In this house, we stan Michael Callan’s underrated self!
That Funny Feeling (1965)
Troubling: In one scene, a white character puts on a racist “Japanese” accent and slants her eyes.
Fun: Sandra Dee is stunning here and so is Bobby Darin, and I used to watch this movie every night to fall asleep when I was 15.
A Man Could Get Killed (1966)
Troubling: Genuinely cannot recall. It’s on the rewatch list. Although, certainly troubling: the presence of Anthony Franciosa, an actor I hate for no actual reason.
Fun: Sandra Dee and James Garner in global spy fun!
The Glass Bottom Boat (1966)
Troubling: 100% someone puts on some culturally appropriative outfits at some point.
Fun: Doris Day’s rom-com swansong. She’s effervescent.
How Sweet It Is! (1968)
Troubling: Idk, again I need to rewatch (this list is a scam), but I just assume there has to be stuff in there.
Fun: Debbie Reynolds getting to go full wild and fun! James Garner still killing it. EXCLAMATION POINT! titles are how you know a 1960s romcom is gonna be good.
