Film

Avanti!

A 1972 Billy Wilder comedy about an uptight American executive sent to Italy to retrieve his father's body, only to discover the old man died with his mistress—and her daughter is very much alive and interested in him. Lemmon at his best: flustered, verbal, desperately trying to maintain composure while romance blooms. Witty, generous-hearted, and genuinely sexy in a way comedies rarely are now.

TMDb rating3.5

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Some Like It Hot1959

The definitive Lemmon comedy: he's a musician on the run, hiding as a woman in an all-female band. Wilder directing again. Funny, fast, and the template for everything that followed.

But The drag element is sometimes played for laughs in ways that feel dated. It's also nearly two hours and takes its time setting up.

Some Like It Hot poster

The Apartment1960

Lemmon and Wilder's masterpiece: a meek insurance clerk lets his bosses use his apartment for affairs, then falls for the elevator girl. Romance, comedy, and genuine melancholy woven together perfectly.

But It's emotionally serious underneath the laughs. If you want pure comedy lightness, this will occasionally break your heart.

The Apartment poster

Breakfast at Tiffany's1961

Audrey Hepburn as the incandescent Holly Golightly, a woman nobody can quite pin down. Romantic, funny, gorgeously shot, and endlessly rewatchable. The definition of effortless charm.

But The central plot hinges on a problematic decision. It's also very much a product of its time, and some attitudes haven't aged gracefully.

Breakfast at Tiffany's poster

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Mon Oncle1958

Both are about an older man out of step with the modern world, fumbling through situations with physical comedy and genuine warmth. Both use mise-en-scène to tell jokes instead of dialogue.

Jacques Tati as M. Hulot, navigating a ultra-modern suburban villa with deadpan confusion. Pure visual comedy without relying on plot or dialogue. A masterclass in filmmaking and observation.

But There's almost no plot. It requires patient, active watching and rewards close attention, not passive enjoyment. Entirely in French.

Mon Oncle poster
More like this (8)

The Pink Panther1963

Peter Sellers as Inspector Clouseau, a bumbling detective on the trail of a jewel thief. Physical comedy at the highest level, absurdist humor, and Sellers is simply unstoppable.

But The humor is slapstick and often repetitive. If broad physical comedy isn't your thing, you'll find it wearing.

The Pink Panther poster

A Shot in the Dark1964

Sellers returns as Clouseau; the comedy reaches new heights. The script is tighter, the jokes land harder, and there's real chemistry between Sellers and Elke Sommer.

But Still very much in the slapstick register. Also, like all Clouseau films, it relies on the same comedic formula.

A Shot in the Dark poster

Singin' in the Rain1952

Gene Kelly, Donald O'Connor, and Debbie Reynolds in the greatest musical comedy ever made. The numbers are joyful, the dancing is transcendent, and the humor is genuinely clever.

But It's a musical, so if song-and-dance numbers aren't your speed, this won't work. Also quite dated in its gender dynamics.

Singin' in the Rain poster

Roman Holiday1953

Audrey Hepburn and Gregory Peck as a runaway princess and a reporter falling in love over 24 hours in Rome. Romantic, charming, beautifully shot, and surprisingly tender.

But The plot is thin and relies entirely on star charisma. Some find it too sentimental by modern standards.

Roman Holiday poster

It Happened One Night1934

Claudette Colbert and Clark Gable as a runaway heiress and a reporter who fall in love on the road. Fast, funny, and genuinely romantic. The template for all romantic comedies.

But It's 90 years old and it shows. The pacing is slow by modern standards, and the gender politics are what you'd expect from 1934.

It Happened One Night poster

Tootsie1982

Dustin Hoffman as an out-of-work actor who disguises himself as a woman to get a role. Funny, touching, and surprisingly smart about gender, performance, and self-deception.

But At 116 minutes it feels a little long. Also, the gender politics, while progressive for 1982, have some awkward moments now.

Tootsie poster

Under the Tuscan Sun2003

Both center on romantic awakening in Italy, but where Avanti! is witty and sophisticated, this is earnest and aspirational. They're opposite tones for the same fantasy.

Diane Lane as a recently divorced woman who impulsively buys a villa in Italy and rebuilds her life. It's escapist, genuinely funny, and has real emotional stakes beneath the fantasy.

But It's aggressively feel-good and doesn't pretend otherwise. Some will find it saccharine or wish it had more narrative teeth.

Under the Tuscan Sun poster

Bread and Chocolate1974

Made a year after Avanti!, also set partly in Italy, also about a man out of place trying to navigate a foreign world and romantic connection. But this is a blue-collar tragedy-comedy where Avanti! is elegant farce.

Nanni Moretti as an Italian immigrant in Switzerland trying to assimilate and find love. It's funny and touching, a comedy that never forgets the loneliness underneath.

But It's in Italian with subtitles. The tone shifts between comedy and sadness, which can feel uneven if you're not expecting it.

Bread and Chocolate poster

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