Film

Under the Yum Yum Tree

A 1963 sex comedy about a lecherous landlord pursuing his young tenant while her fiancé is away. It's broad, breezy, and stuffed with double entendres—the kind of film that works hardest when you're not taking anything seriously. For anyone curious how Hollywood played romance before the sexual revolution fully landed.

TMDb rating3.1

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The Apartment1960

Lemmon's earlier comedy about a man bent on seduction, but with actual warmth and heartbreak underneath. A masterpiece of the era that does everything this film attempts, infinitely better.

But It's longer and far more emotionally demanding. You have to actually care about the characters.

The Apartment poster

Breakfast at Tiffany's1961

Audrey Hepburn and Henry Mancini create something genuinely magical in this love story. A '60s romantic comedy that still works because it has style, wit, and a real heart.

But The pacing is deliberate. If you want constant laughs and movement, it'll feel slow.

Breakfast at Tiffany's poster

Send Me No Flowers1964

Rock Hudson and Doris Day navigate marital chaos with charm and impeccable timing. A perfectly constructed farce that knows exactly what it's doing.

But The whole film rests on a premise that's fundamentally mean-spirited if you think about it too hard.

Send Me No Flowers poster

Not sure tonight? Get a pick in a minute, starting from Under the Yum Yum Tree

The wildcard

Something you would not have found on your own.

Breakfast on Pluto2005

Both are fundamentally about someone pursuing connection across a power or social imbalance, but Breakfast on Pluto asks what that actually costs and doesn't let desire excuse cruelty.

Cillian Murphy as a transgender Irish woman seeking love and belonging in 1970s London and Berlin. It's anarchic, tender, chaotic, and genuinely alive in ways that make '60s sex comedies look frozen in amber.

But It's structurally messy and emotionally demanding. The tone whipsaws between lightness and real trauma.

Breakfast on Pluto poster
More like this (8)

Lover Come Back1961

Hudson and Day again, in a screwball advertising comedy with genuine chemistry and surprising sexual confidence for its time. Moves like a dream.

But The advertising world satire dates badly. Some of the 'shocking' moments play as quaint now.

Lover Come Back poster

Barefoot in the Park1967

Redford and Fonda navigate newlywed chaos with real affection. Lighter than The Apartment but with genuine emotional stakes and better dialogue.

But It's very much a stage adaptation. The New York apartment setting gets repetitive.

Barefoot in the Park poster

Move Over, Darling1963

Doris Day and James Garner in a screwball remarriage comedy. Energetic, funny, and genuinely clever about what happens when you thought your spouse was dead.

But Day's wholesomeness can feel suffocating. The film never lets itself get truly weird.

Move Over, Darling poster

The Graduate1967

Dustin Hoffman's seduction by Anne Bancroft and his pursuit of her daughter is the dark mirror to every landlord-tenant comedy. Darkly funny and genuinely unsettling.

But It's a downer dressed as a comedy. The ending won't make you feel good.

The Graduate poster

Pillow Talk1959

Hudson and Day's first pairing is a party-line romantic farce with infectious energy. The chemistry is undeniable and the central conceit is genuinely clever.

But It's a artifact of its era. Some of the gender politics will make you wince.

Pillow Talk poster

That Funny Feeling1965

Sandra Dee and Bobby Darin in a light romantic comedy about class and pretense. Sweet-natured and breezier than most of these, with decent laughs.

But It's the least substantial film on this list. There's not much to it beyond the charm of the leads.

That Funny Feeling poster

Tootsie1982

Both center on a man pursuing a woman by fundamentally misrepresenting himself, but Tootsie understands that deception has a moral weight—and a cost.

Dustin Hoffman as a man who cross-dresses to get a role, then falls for Jessica Lange. It looks like a comedy but it's actually about deception, authenticity, and what we owe each other.

But The gender politics are complicated. Some moments read very differently now than they did in 1982.

Tootsie poster

Some Like It Hot1959

Like Under the Yum Yum Tree, it's a sex comedy about deception and desire, but Wilder weaponizes the form to say something genuinely true about gender, performance, and who we really are.

Lemmon and Curtis disguise themselves as women to escape the mob, and Billy Wilder makes it absurdist perfection. It's the best sex comedy ever made, period.

But If you're not in the mood for constant frenetic energy and rapid-fire one-liners, it's exhausting. The plot stops mattering by the halfway point.

Some Like It Hot poster

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