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Movies that feel like Harold and Maude (1971)

If you loved Harold and Maude, the closest films we have are Annie Hall (1977), The Apartment (1960) and Two for the Road (1967). All three share Harold and Maude's witty and playful feel, which is what we rank on before quality. 7 of the 12 picks below are included with a subscription right now on YouTube TV, MGM Plus and Netflix and others, checked against today's data.

A deadpan young man obsessed with death meets an eccentric septuagenarian who teaches him to live life to the fullest.

πŸ… 86% Rotten Tomatoesβ˜… 7.8 IMDb β†—TMDB β†—dir. Hal Ashbywittyplayfulcontemplativeromantictender

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If Harold and Maude hit the spot, these will too

Annie Hall poster
Annie Hall
1977 Β· dir. Woody Allen
πŸ… 97%β˜… 7.9comedy Β· drama Β· romance

The same mix in both: wit, then play

New York comedian Alvy Singer falls in love with the ditsy Annie Hall.

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The Apartment poster
The Apartment
1960 Β· dir. Billy Wilder
πŸ… 93%β˜… 8.3comedy Β· drama Β· romance

Both circle age difference and suicide attempt

Bud Baxter is a minor clerk in a huge New York insurance company, until he discovers a quick way to climb the corporate ladder. He lends out his apartment to the executives as a place to take their mistresses. Although he often has to deal with the aftermath of their visits, one night he's left with a major problem to solve.

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Two for the Road poster
Two for the Road
1967 Β· dir. Stanley Donen
πŸ… 82%β˜… 7.4drama Β· romance Β· comedy

Contemplative where it counts, romantic underneath

Architect Mark Wallace and his wife, Joanna, travel to France to meet with an affluent client. While there, they reflect on their first decade of marriage -- memories of when they first met, of courtship, and of road trips through the French countryside. As flirtation and playful quarreling turn to boredom with the banality of married life, the Wallaces struggle to rekindle their passion, while mutual infidelity threatens to tear them apart.

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Breakfast at Tiffany's poster
Breakfast at Tiffany's
1961 Β· dir. Blake Edwards
πŸ… 87%β˜… 7.5comedy Β· romance Β· drama

Tender comedy, and it commits to that

Holly Golightly is an eccentric New York City playgirl determined to marry a Brazilian millionaire. But when young writer Paul Varjak moves into her apartment building, her past threatens to get in their way.

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Same Time, Next Year poster
Same Time, Next Year
1978 Β· dir. Robert Mulligan
πŸ… 40%β˜… 7.2comedy Β· drama Β· romance

Drama with a pulse of wit, in both cases

The difference: Critics were much harder on this one

A man and woman meet by chance at a romantic inn over dinner and, although both are happily married to others, they find themselves in the same bed the next morning questioning how this could have happened. They agree to meet on the same weekend each yearβ€”in the same hotel roomβ€”and the years pass each has some personal crisis that the other helps them through, often without both of them understanding what is going on.

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Roman Holiday poster
Roman Holiday
1953 Β· dir. William Wyler
πŸ… 97%β˜… 8romance Β· comedy Β· drama

Romance built on play, twice over

Overwhelmed by her suffocating schedule, touring European princess Ann takes off for a night while in Rome. When a sedative she took from her doctor kicks in, however, she falls asleep on a park bench and is found by an American reporter, Joe Bradley, who takes her back to his apartment for safety. At work the next morning, Joe finds out Ann's regal identity and bets his editor he can get exclusive interview with her, but romance soon gets in the way.

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Say Anything... poster
Say Anything...
1989 Β· dir. Cameron Crowe
πŸ… 98%β˜… 7.3romance Β· comedy Β· drama

Both trade on stillness more than on being comedy

Average student and eternal optimist Lloyd Dobler seeks to capture the heart of Diane Court, a beautiful but unattainable valedictorian classmate. He surprises just about everyone - including himself - when she returns the sentiment. However, Diane's divorced, over-protective father soon begins to disapprove of the match, and Lloyd realises that it's going to take more than just the power of love to conquer all.

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Dilwale Dulhania Le Jayenge poster
Dilwale Dulhania Le Jayenge
1995 Β· dir. Aditya Chopra
πŸ… 100%β˜… 8comedy Β· drama Β· romance

Romantic drama in both cases

The difference: A 1990s film, from a different era of filmmaking

Raj is a rich, carefree, happy-go-lucky second generation NRI. Simran is the daughter of Chaudhary Baldev Singh, who in spite of being an NRI is very strict about adherence to Indian values. Simran has left for India to be married to her childhood fiancΓ©. Raj leaves for India with a mission at his hands, to claim his lady love under the noses of her whole family. Thus begins a saga.

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Strictly Ballroom poster
Strictly Ballroom
1992 Β· dir. Baz Luhrmann
β˜… 7.2comedy Β· drama Β· romance

Romance built on tenderness, twice over

Brave new steps put Scott's career in jeopardy. With a new partner and determination, can he still succeed?

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Jerry Maguire poster
Jerry Maguire
1996 Β· dir. Cameron Crowe
πŸ… 86%β˜… 7.3comedy Β· drama Β· romance

Comedy with a pulse of wit, in both cases

Jerry Maguire used to be a typical sports agent: willing to do just about anything he could to get the biggest possible contracts for his clients, plus a nice commission for himself. Then, one day, he suddenly has second thoughts about what he's really doing. When he voices these doubts, he ends up losing his job and all of his clients, save Rod Tidwell, an egomaniacal football player.

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I Know Where I'm Going! poster
I Know Where I'm Going!
1945 Β· dir. Emeric Pressburger
πŸ… 100%β˜… 7.4romance Β· drama Β· comedy

Drama built on play, twice over

Plucky Englishwoman Joan Webster travels to the remote islands of the Scottish Hebrides in order to marry a wealthy industrialist. Trapped by inclement weather on the Isle of Mull and unable to continue to her destination, Joan finds herself charmed by the straightforward, no-nonsense islanders around her, and becomes increasingly attracted to naval officer Torquil MacNeil, who holds a secret that may change her life forever.

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Love Actually poster
Love Actually
2003 Β· dir. Richard Curtis
πŸ… 65%β˜… 7.5comedy Β· romance Β· drama

Romance built on stillness, twice over

Eight very different couples deal with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London.

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The best-reviewed films that share Harold and Maude's defining feeling.