Themes explored through fictional works don’t tend to get much broader or more commonplace than that of love (even if other contenders like “death” and “greed” give it some competition). For almost as long as film has existed as a medium, romantic stories and ideas have been explored and presented on screen. Given how many movies showcase or at least partly deal with romance, it’s not surprising to see that many romance films have done well at the Oscars over the decades.
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The following Best Picture winners all explore the topic of love thoroughly, and can count themselves as romance films (while tending to cross over into some other genres). While there are more than 22 Best Picture winners that feature some sort of romance – and it’s probably easier to list winners that don’t have any romance elements – the following titles are defined by the way they put such stories front and center. These Best Picture-winning romance movies are ranked below, starting with the decent and ending with the great.
22 ‘Gigi’ (1958)
Director: Vincente Minnelli
Image via MGM
There’s a chance Gigi might’ve felt old-fashioned even back in 1958, given its story is set at the start of the 20th century and revolves around some very “traditional” ideas of romance. It’s also a musical (not a great one), and has a generally light-hearted tone in the telling of its story about a young girl in Paris being shaped into a desirable potential wife for a wealthy bachelor.
Nowadays, much of Gigi comes across as a little uncomfortable at best and hopelessly regressive/unpleasant at worst, and given what it covers, it’s hard to get swept up in much of the romance presented here. At least the movie is well-presented, and even if it’s nowadays a little baffling to learn it won Best Picture, awards in Oscar categories like Best Art Direction and Best Costume Design were well-deserved.
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21 ‘Shakespeare in Love’ (1998)
Director: John Madden
Image via Miramax
One of the more comedic and bubbly Best Picture winners of the past few decades, Shakespeare in Love could be considered anywhere from detestable to over-hated, depending on who you ask. It’s become strangely divisive for a movie that takes a rather breezy approach to the story at hand, which focuses on William Shakespeare as he tries to write Romeo and Juliet while having something of a tumultuous love life himself.
It’s got a historical setting, some heartfelt romantic drama, and plenty of broad comedy, making it the kind of thing that was perhaps set up – in some ways – to deal with the kind of itch that Oscar voters specifically often need scratching. Trying to view it as objectively as possible, it’s not a travesty of a film (and there are worse/less popular Best Picture winners), though it is one of the weaker romance-centered ones to win that top award on Oscar night.
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20 ‘Tom Jones’ (1963)
Director: Tony Richardson
Image via United Artists
Tom Jones has, by Best Picture winner standards, faded into obscurity to some degree, and sometimes gets labeled as a lesser winner of such an Academy Award, perhaps similarly to Shakespeare in Love. It’s not a great or essential winner, sure, but it’s definitely not that bad, and proves to be a fun blend of adventure, comedy, and romance genres, all combined in a way that feels simultaneously old-fashioned and fresh (for its time).
The titular character is a rebellious young man who lives to fall in love, seemingly over and over again, but then finds someone who could become something more permanent… though unfortunately, the two are at odds due to their differing backgrounds. Tom Jones has a historical setting, playing out in the 1700s, but the style and spirit of the film prove undeniably 1960s, and such a clash does prove to be – at least sometimes – intoxicating and novel.
Tom Jones (1963)
Release Date August 24, 1963
Director Tony Richardson
Cast Albert Finney , Susannah York , Hugh Griffith , Edith Evans , Joan Greenwood , Diane Cilento
Runtime 129 minutes
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19 ‘The English Patient’ (1996)
Director: Anthony Minghella
Image via Miramax
A World War II drama that manages to find plenty of time for a romance story (undoubtedly helped by the fact that it runs for more than 160 minutes), The English Patient is a solid epic film. Perhaps it’s another that might not feel as deserving of Best Picture as some other films of its time (it wasn’t nominated, but how cool would it have been if something as groundbreaking and timeless as 1996’s Trainspotting had won?), but taken on its own merits, it’s still far from bad.
Much of the story revolving around tragedy, love, and heartbreak plays out in a series of flashbacks, told by a mysterious injured man at some point after the conclusion of World War II. The English Patientticks all the boxes that a big Academy Awards winner needs to do, for better or worse, and as a result, was handsomely rewarded by Oscar voters with an impressive nine trophies, including Best Director (Anthony Minghella) and Best Picture.
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18 ‘Out of Africa’ (1985)
Director: Sydney Pollack
Image via Universal Pictures
Honing in on the romance-centered parts of the life of its subject, Karen Blixen, Out of Africaultimately serves as both a biographical movie and a romantic one. Blixen (Meryl Streep) was an author who decided to change her life drastically near the start of the 20th century by going to live in Africa. While there, she ended up falling in love with Denys Finch Hatton (Robert Redford), a well-known hunter.
If you think that might all sound a little simple for a movie that runs for more than 2.5 hours, you could well be right, as Out of Africa is a film where you feel the length, and one where it doesn’t always feel like there’s a lot happening. Still, both Streep and Redford are very good together, elevating the material at hand, and the film also looks and sounds great (the latter courtesy of composer John Barry).
Out of Africa
Release Date December 20, 1985
Director Sydney Pollack
Runtime 150
Main Genre Biography
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17 ‘Gone with the Wind’ (1939)
Director: Victor Fleming
Image via Loew’s Inc.
There are many things to be said about Gone with the Wind, considering its complex legacy and the way aspects of it have been reassessed, and so too are there many things the film is attempting to be. It’s a drama about the Civil War, undeniably feels like an epic thanks to its runtime and scope, and also aims to tell a romantic story about two people who aren’t really right for each other while never feeling ready to let the other go.
By some metrics, Gone with the Wind is an all-time great cinematic achievement, and then, when viewed in another way, it can feel oddly shameful and worthy of more criticism than praise. History doesn’t lie, though, when it comes to the fact that Gone with the Wind won over audiences and Oscar voters alike, and exists in all its complex glory today as another romance-heavy film that won Best Picture at the Academy Awards.
Gone With the Wind
Release Date January 17, 1940
Director Victor Fleming , George Cukor , Sam Wood
Cast Thomas Mitchell , Barbara O’Neil , Vivien Leigh , Evelyn Keyes , Ann Rutherford , George Reeves , Hattie McDaniel
Runtime 238 minutes
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16 ‘From Here to Eternity’ (1953)
Director: Fred Zinnemann
Image via Columbia Pictures
To quote Larry David, From Here to Eternity is pretty, pretty, pretty good; perhaps even nothing more or less. It may have half the runtime of Gone with the Wind, but it throws together certain elements in a comparable way, this time focusing on World War II instead of the Civil War and spending time highlighting the romances of various people wrapped up in it.
Calling From Here to Eternity a romantic melodrama set against the backdrop of war, therefore, is not at all an unfair description, but as far as this sort of historical drama/romance movie goes, it executes things well. It also has a cast of classic Hollywood stars to die for, with the names attached to From Here to Eternity including the likes of Burt Lancaster, Montgomery Clift, Deborah Kerr, Donna Reed, and Frank Sinatra.
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15 ‘You Can’t Take It with You’ (1938)
Director: Frank Capra
Image via Columbia Pictures
Frank Capra made the kind of dependable movie he so often proved capable of making with 1938’s You Can’t Take It with You, and it ended up being another Best Picture winner within his filmography (more on the earlier – and superior – winner of his in a bit). Narratively, it’s simple, being about the clash between two families of different classes when young members of each family fall in love.
That class clash is less violent and tragic than what’s found in another Best Picture-winning movie about family and class (2019’s Parasite), with You Can’t Take It with You instead exploring such things through the rom-com genre. It’s lost a little of its bite in the decades since its release, but it’s still a film with likable performances and does hold up as more than watchable, being a well-executed comedy-drama with some genuinely sweet romance at its center.
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14 ‘My Fair Lady’ (1964)
Director: George Cukor
Image via Paramount
An extravagant and lengthy musical that’s ultimately worth devoting almost three hours to, My Fair Lady is also well-recognized for containing what might be Audrey Hepburn’s most iconic performance. Like Gigi from several years earlier, the premise of My Fair Lady – involving one man betting that he can transform a working-class girl into a sophisticated lady – feels dated, but it’s overall handled a little better in this film.
It’s not a downbeat film, but it balances moments of levity with some drama, in turn taking parts of the premise seriously and calling attention to some of the problems involved with the way characters behave. That’s not to say that My Fair Lady has aged perfectly, and nor will it likely appeal to those who aren’t wild about musicals… but it is a well-told romance film, in the end, and also proves dazzling from a technical standpoint.
My Fair Lady
Release Date October 21, 1964
Director George Cukor
Cast Audrey Hepburn , Rex Harrison , Stanley Holloway , Wilfrid Hyde-White , Gladys Cooper , Jeremy Brett
Runtime 170
Main Genre Drama
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13 ‘Marty’ (1955)
Director: Delbert Mann
Image via United Artists
Marty is a short and sweet romantic drama, so brief in runtime, in fact, that it has the distinction of being the shortest Best Picture winner in the history of the Academy Awards. The film’s titular character is a working-class man in his mid-30s who doesn’t seem to be going many places in life, and begins to find extra purpose within said life after he meets a schoolteacher who he instantly has a connection with.
Conflict ensues when his parents don’t think she’ll be a suitable partner for Marty, with the film being about standing up for what you believe or feel as well as looking at disagreements between generations and the way they see the world. Marty is a very straight-to-the-point movie that works because of how down-to-earth it feels, both through its filmmaking and the inherent naturalness of the performances contained within.
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12 ‘The Artist’ (2011)
Director: Michel Hazanavicius
Image via Warner Bros.
Some will say The Artist is one of the weaker winners of Best Picture in recent memory, but that feels a little harsh, because it’s an unpretentious movie and it came out in a year that wasn’t particularly competitive as far as Oscar contenders were concerned. It’s a nice and breezy homage to cinema of old, taking place during the silent era and following one movie star struggling to adapt to the transition to talkies.
The Artist has one central gimmick used while telling this story: the film itself is almost entirely silent, and filmed in black and white to give the impression that it might well have been made around the time it’s set. It’s got heart, some gentle comedy, a decently executed central romance, and a memorable dog sidekick for the main character; not the most ambitious Best Picture winner or anything, but it succeeds in what it’s going for and ends up being a fun watch.
The Artist
Release Date January 20, 2012
Director Michel Hazanavicius
Runtime 100 minutes
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11 ‘The Sound of Music’ (1965)
Director: Robert Wise
Image via 20th Century Fox
An all-time great musical that’s based on a true story and centers quite heavily on romance, The Sound of Music is the sort of classic that has a reputation that precedes it. It won the year after My Fair Lady did, and takes a similar sort of approach to the musical genre, being something of an epic and also feeling a little old-fashioned in a way that will charm musical lovers while potentially alienating those who aren’t big on the genre.
The story follows a young woman being assigned as a governess at the home of a wealthy widow, looking after (and bonding with) his seven children while slowly falling in love with the widow himself. It works well, and it’s easy to see why so much of The Sound of Music has become so iconic, even if most of the stuff people love about it can be found in the first two hours (and that final act, as a result, does drag just a little bit).
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10 ‘Wings’ (1927)
Director: William A. Wellman
Image via Paramount Pictures
The very first winner of Best Picture (sort of; there were kind of two winners – more on the other in a bit) was the ambitious epic that was Wings, and it also ranks among the most action-packed winners of said award in Oscar history. At its core is a story about two pilots during World War I both falling for the same woman, effectively being a love triangle romance that’s inevitably at its most interesting when it’s depicting dogfights.
As such, Wings is perhaps a better action/war movie than it is a romance film, but that romantic side of the story still works well and generates some extra emotion/tension for the overall film. The love story is dated, but in a way that may be charming, while the more exciting and action-centered scenes in the film still hold up shockingly well almost a century on from release.
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9 ‘An American in Paris’ (1951)
Director: Vincente Minnelli
Image via Loew’s Inc.
A defining musical that’s influenced movies as recently as 2016’s La La Land, An American in Paris is very old-fashioned and unapologetically Hollywood in its approach to romance, comedy, and music. Still, there is an inherent charm about this movie that’s hard to resist, and its overall breezy nature and intentional goofiness (in parts) do make it feel harder to criticize.
Those entering into An American in Paris knowing things will be lightweight, colorful, and carefree should hopefully have a good time with it, and even skeptics might be converted when seeing musical pros like Gene Kelly and Leslie Caron dance up a storm. The film is less concerned with portraying a convincing romance (though it doesn’t do so badly) and more focused on delivering colorful – and sometimes fantastical – song-and-dance numbers, and it’s during these sequences that An American in Paris shines.
An American in Paris
Release Date September 26, 1951
Director Vincente Minnelli
Cast Gene Kelly , Leslie Caron , Oscar Levant , Georges Guétary , Nina Foch , The American In Paris Ballet
Runtime 113
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8 ‘The Shape of Water’ (2017)
Director: Guillermo del Toro
Image via Fox Searchlight Pictures
Before The Shape of Water, the fantasy genre hadn’t been particularly well-represented at the Oscars as far as Best Picture winners were concerned. The Lord of the Rings: The Return of the King had deservedly won 14 years earlier, but The Shape of Water was a different kind of fantasy movie, feeling a little darker, certainly less epic, and revolving around an unlikely romance.
That central romance does involve the bond between a mute janitor and some sort of half-man/half-fish creature, and honestly, if that’s a barrier for some people getting into The Shape of Water, maybe that’s understandable. But Guillermo del Toro executes this unlikely premise remarkably well, giving the film a strong central story, memorable characters both good and evil, and a great amount of heart, all while crafting something undoubtedly unique.
The Shape of Water
Release Date December 1, 2017
Director Guillermo del Toro
Runtime 123
Main Genre Drama
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7 ‘Sunrise: A Song of Two Humans’ (1927)
Directed by F. W. Murnau
Image via Fox Film Corporation
1927 was a pivotal year for cinema, given it was the year when talkies started to enter the picture, and because films that year were the first to be awarded Oscars at the first-ever ceremony. Also interesting was the fact that the first Academy Awards ceremony presented two awards comparable to the modern day’s Best Picture award, with the aforementioned Wings winning “Outstanding Picture” and Sunrise: A Song of Two Humans winning Unique and Artistic Picture.
This category of Unique and Artistic Picture was only used once, but still, it’s possible to argue Sunrise: A Song of Two Humans is a Best Picture winner nonetheless… and perhaps even more deserving of the award than Wings. It’s a more personal and heartfelt film, showcasing the rocky romance between two people, overall feeling tender and universal in a way that still gives Sunrise: A Song of Two Humans a surprising amount of emotional power to this day.
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6 ‘Titanic’ (1997)
Directed by James Cameron
Image via 20th Century Fox
It’s hard to accuse a filmmaker with ambitions as grand as James Cameron’s of not swinging for the fences, and it’s especially hard to do so when he makes a movie that’s got the kind of epic scope Titanic does. This epic runs for more than three hours and feels like at least two movies in one, especially because the first half is a romantic melodrama and the second half becomes a full-on disaster movie.
It’s a testament to Cameron’s craft that such approaches to the two halves still blend, and Titanic successfully ended up being the kind of movie that could appeal to everyone, in some way or another. It was a huge box office hit (an understatement, really), and then a mammoth success at the Academy Awards, winning 11, including Best Director (Cameron) and Best Picture.
Titanic
Release Date November 19, 1997
Director James Cameron
Runtime 194 minutes
Main Genre Drama
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5 ‘Annie Hall’ (1977)
Director: Woody Allen
Image via United Artists
Woody Allen has made plenty of movies, and many are comparable (or even bleed into one another, to some extent). Despite this, various films of his haven’t aged the best, nor prove particularly memorable, but he’s made some classics throughout his long and controversial career, and of those, it’s arguably 1977’s Annie Hall that holds up the best.
Maybe some would’ve preferred a certain movie set a long time ago in a galaxy far, far away to have won 1977’s Best Picture Oscar, but Annie Hall is so well-written, funny, and honest about the nature of relationships in the 20th century that it still feels like a deserving winner. It’s a film mostly just made up of people talking to each other and a narrator interjecting with anxiety-filled thoughts, but it’s so well-executed and constructed overall that it’s hard to deny the humor and insight contained within.
Annie Hall
Release Date April 19, 1977
Director Woody Allen
Runtime 93
Main Genre Comedy
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4 ‘The Apartment’ (1960)
Director: Billy Wilder
Image via United Artists
In a decades-long career, Billy Wilder seemed capable of doing it all, making definitive film noir masterpieces, gritty dramas, and hilariously farcical comedies, mostly during the 1940s, ’50s, and even into the ‘60s. The Apartment is up there with his best films overall, and manages to successfully blend a story about love into a film that perfectly balances comedy and drama throughout.
The premise is about various higher-ups at a workplace wanting to conduct extramarital affairs, and an ambitious young worker offering his apartment as a place for them to do it, which causes complications as things go on. It’s very surprising how well The Apartment holds up all these decades later, ultimately being boosted by Wilder’s skilled direction, the strength of the two lead performances (from Jack Lemmon and Shirley MacLaine), and the impossibly tight and witty screenplay holding it all together.
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3 ‘West Side Story’ (1961)
Directors: Robert Wise and Jerome Robbins
Image via United Artists
One year after The Apartment, another romance movie won Best Picture: West Side Story. However, the approaches taken by both films toward the central theme/premise of love couldn’t have felt more different. The Apartment is generally comedic, and mostly a good time to watch, while West Side Story is unequivocally a tragic romance, perhaps a consequence of it being an updated take on the infamously downbeat Romeo and Juliet.
West Side Story also happens to be an incredible musical, and it tells a gripping story about gang warfare and the consequences involved for all when two people on opposing sides of such a conflict find themselves falling in love. It’s shot and presented in a grand and old-school way, and the core emotional aspects of the film still shine through and hit hard, making it one of the very best classic musicals/romance movies/crime films of its era.
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