14 Great Romantic Comedies That Ruled The Oscars

The romantic comedy genre has had a weird couple of years, suffering at the box office and earning a reputation as a "chick" genre with little to offer the general public. Once a mighty force to be reckoned with at the box office, the rom-com saw a steep decline throughout the 2010s. However, the recent

The romantic comedy genre has had a weird couple of years, suffering at the box office and earning a reputation as a "chick" genre with little to offer the general public. Once a mighty force to be reckoned with at the box office, the rom-com saw a steep decline throughout the 2010s. However, the recent success of Anyone But You suggests the rom-com is making a comeback, just in time to retake its place as one of cinema's leading genres.

Some rom-coms even make it all the way to the Oscars, an impressive feat considering the Academy's traditional tastes. Classics like Roman Holiday are the perfect reminder of how big some rom-coms got at the Oscars, with a few even receiving Best Picture nominations. And even if only a few claimed the award, their place among the nominees is a victory in and of itself.

1 'It Happened One Night' (1934)

Director: Frank Capra

Widely considered one of the all-time best films, let alone the all-time best romantic comedies, It Happened One Night ruled the 1935 Oscars. The story centers on the unexpected romance between a spoiled socialite and a cynical reporter as they are forced to travel together after becoming stranded. Clark Gable and Claudette Colbert star under the direction of the legendary Frank Capra.

Upon release, the film received near-universal acclaim from critics and was a massive box-office success. It Happened One Night was the first of three films to win the Big Five Oscars: Picture, Director, Actor for Gable, Actress for Colbert, and Screenplay. It remained the only picture to win both Lead Actor and Actress for forty-one years until One Flew Over the Cuckoo's Nest joined it.

It Happened One Night
ComedyRomance

A renegade reporter trailing a young runaway heiress for a big story joins her on a bus heading from Florida to New York, and they end up stuck with each other when the bus leaves them behind at one of the stops.

Release Date February 22, 1934 Cast Clark Gable , Claudette Colbert , Walter Connolly , Roscoe Karns Runtime 105 minutes

Rent on Amazon

2 'The Philadelphia Story' (1940)

Director: George Cukor

The Philadelphia Story stars a trio of true cinematic icons: Katharine Hepburn, Jimmy Stewart and Cary Grant. Based on Philip Barry's eponymous play, the plot centers on a wealthy but spoiled socialite whose wedding plans get disrupted by the sudden arrival of her ex-husband and a tabloid journalist on the eve of her wedding.

A massive critical and commercial success, The Philadelphia Story received six Oscar nominations, including Best Picture. Stewart won Best Actor, his only competitive win at the Oscars, while Hepburn received her third nomination; sadly, Grant was snubbed for his efforts. The Philadelphia Story remains a classic of the beloved genre, to the point where even people who don't like romantic comedies will enjoy the hijinks of Hepburn's spirited socialite.

Watch on Tubi

3 'Roman Holiday' (1953)

Director: William Wyler

Audrey Hepburn made her film debut opposite Gregory Peck in William Wyler's Roman Holiday. The plot follows Ann, the princess of an unnamed European country, who joins reporter Joe on a trip to see Rome away from her overbearing royal duties. Unbeknownst to her, Joe is looking for an exclusive on the princess' life, but romance will derail both of their plans.

A smashing box office and critical success, Roman Holiday received a total of ten Oscar nominations. Hepburn became the first actor to win the Oscar, Golden Globe and BAFTA for a single role, and the film also received trophies for Best Story and Best Costume Design - Black and White. Unfortunately, the film's writer, Dalton Trumbo, didn't receive credit for his work since he was on the Hollywood Blacklist at the time.

Watch on Paramount+

4 'Gigi' (1958)

Director: Vincente Minnelli

Based on Colette's 1944 eponymous novella, Gigi stars Leslie Caron in the titular role opposite Louis Jourdan. The plot concerns the friendship of Gigi, a young girl learning the ways of society, and Gaston, a dashing playboy unwilling to commit. When the possibility of romance arises, Gaston must decide between his feelings for Gigi and his carefree, debauched lifestyle.

Gigi won all nine of its nominations at the 31st Oscars, including Best Picture. Minnelli won his only Oscar for Best Director, while the film's now-famous production values also prevailed. Interestingly, neither Caron nor Jourdan received nominations for their work. Nowadays, Gigi is widely considered among the best musicals from the 1950s and a stellar example of the decade's larger-than-life approach.

Watch on Tubi

5 'The Apartment' (1960)

Director: Billy Wilder

Billy Wilder's timeless classic The Apartment centers on an insurance clerk, played by Jack Lemmon, who allows the senior members of his company to use his apartment to conduct their extramarital affairs. Things become complicated when he develops feelings for an elevator operator, played by Shirley MacLaine, who's having an affair with his boss.

Critically lauded for its humor and romance and with one of cinema's most unforgettable closing lines, the film was an instant and overwhelming success. The Apartment received ten Oscar nominations and won five, including Best Picture and Director for Wilder. To this day, many believe MacLaine should've won Best Actress, but she faced tough competition from Elizabeth Taylor, who was then recovering from a dangerous surgery.

Watch on Tubi

6 'The Graduate' (1967)

Director: Mike Nichols

The Graduate features two timeless performances from Dustin Hoffman, in his breakthrough role, and Anne Bancroft. The plot concerns Benjamin Braddock, a recent college graduate who enters an affair with Mrs. Robinson, the older wife of his father's law partner. However, things become complicated when Benjamin falls for Mrs. Robinson's daughter, Elaine.

A masterpiece of the genre, The Graduate earned an impressive seven Oscar nominations at the 1968 ceremony, including acting nods for Hoffman, Bancroft, and Katherine Ross. However, the film's only victory came with a Best Director Oscar for Nichols. Not that it has affected the film's reputation, as The Graduate remains widely praised as an influential entry in the New Hollywood wave.

The Graduate
PGComedyDramaRomance

Release Date December 21, 1967 Cast Anne Bancroft , Dustin Hoffman , Katharine Ross , William Daniels , Murray Hamilton , Elizabeth Wilson Runtime 107 minutes

Rent on Amazon

7 'Annie Hall' (1977)

Director: Woody Allen

Neurotic, charming, and with one of the sharpest and funniest screenplays in cinematic history, Annie Hall is among the all-time best romances. The movie chronicles the rise and fall of the relationship between comedian Albie Singer and nightclub singer Annie Hall. As Albie ponders about the failed romance, he offers insightful observations about the nature of love and connection.

Diane Keaton became an instant cinematic icon with her quirky performance as Annie Hall, and the film often ranks among the all-time best comedies. Annie Hall was nominated for the Big Five Oscars and won four: Picture, Director, Actress and Original Screenplay. Annie Hall famously won Best Picture over Star Wars in one of the most memorable Oscar races of the 20th century. Its reputation has only improved over the years, standing as one of the best examples of the rom-com genre.

Annie Hall
PGComedyRomance

Release Date April 19, 1977 Cast Woody Allen , Diane Keaton , Tony Roberts , Carol Kane , Paul Simon , Shelley Duvall Runtime 93 minutes

Watch on Tubi

8 'The Goodbye Girl' (1977)

Director: Herbert Ross

Richard Dreyfuss stars in 1977's The Goodbye Girl, written by the iconic Neil Simon. The plot concerns Elliot, a struggling actor who sublets an apartment from his friend. To his surprise, the apartment is already occupied by Paula, his friend's ex-girlfriend, and her precocious teen daughter, Lucy. An unexpected bond blossoms between the three, leading to a sweet but complicated story.

The Goodbye Girl received five Oscar nominations, including Best Picture. Dreyfuss and co-stars Marsha Mason and Quinn Cummings also received acting nominations, but only Dreyfuss won, becoming the youngest performer to claim the Lead Actor Oscar up to that point. Notoriously, Simon lost the Best Screenplay Oscar to Annie Hall, proving that 1977 was truly a stellar year for the rom-com genre.

Watch on Tubi

9 'Tootsie' (1982)

Dustin Hoffman returns to the rom-com genre with this gem from 1970s cinema that might seem somewhat questionable by today's standards. He plays talented but complicated actor Michael Dorsey, who, in order to secure more work, assumes the identity of a woman in Sydney Pollack's 1982 rom-com Tootsie. The film, one of the funniest comedies of the 80s, co-stars Jessica Lange, Teri Garr and Bill Murray.

The idea of a middle-aged actor becoming a middle-aged actress to land a job might seem ridiculously ironic and inappropriate today, but it was a stroke of genius in 1982. Tootsie earned rave reviews and was a box office juggernaut, securing its place among the Oscar contenders. It received ten nominations but only won one for Jessica Lange's supporting performance.

Watch on Pluto TV

10 'Moonstruck' (1987)

Director: Norman Jewison

Cher and Nicolas Cage star in the 1987 rom-com Moonstruck under the direction of the late great Norman Jewison. The plot centers on Loretta Castorini, an Italian widow who enters an affair with her fiancé's younger and tortured brother shortly after getting engaged. Danny Aiello, Vincent Gardenia and Olympia Dukakis also star.

A critical and financial success, Moonstruck received six Oscar nominations. Cher memorably won Best Actress in one of the Oscar's most competitive races, which also included Glenn Close for Fatal Attraction, Holly Hunter for Broadcast News and Sally Kirkland for Anna. Moonstruck also walked away with the Oscars for Best Supporting Actress for Dukakis and Best Original Screenplay.

Moonstruck
PGComedyDramaRomance Release Date December 16, 1987 Cast Cher , Nicolas Cage , Vincent Gardenia , Olympia Dukakis , Danny Aiello , Julie Bovasso Runtime 102 minutes

Watch on Tubi

11 'Working Girl' (1988)

Director: Mike Nichols

Few directors made more for the romantic comedy genre than Mike Nichols. In 1988, he directed Harrison Ford, Sigourney Weaver and Melanie Griffith in the romantic comedy Working Girl. The film tells the story of Tess McGill, a brilliant but underrated secretary who poses as her boss to rise in the corporate world, only to fall for the investment broker she's working with.

A critical and commercial success, Working Girl received six Oscar nominations, including Best Picture and Best Director. Memorably, Griffith, Weaver, and scene-stealer Joan Cusack all received acting nominations, although sadly, none won, even if many believe Weaver or Cusack should've prevailed in Supporting Actress. Indeed, its sole win was for its anthemic song, Carly Simon's now-iconic "Let the River Run."

Rent on Amazon

12 'As Good As It Gets'

Director: James L. Brooks

Jack Nicholson has starred in numerous movies, but hardly anyone would think of him as a romantic lead in a rom-com. However, that's exactly who he played in 1997's As Good As It Gets, opposite Helen Hunt and Greg Kinnear. The film centers on the unlikely friendship between a misanthropic novelist with OCD, a single mother struggling to support her ill child and a gay painter whose life implodes after being attacked in his apartment.

Although the age difference between Nicholson and Hunt is a tad questionable, the film rises on the strength of the main trio's acting and Brooks' sweet, witty screenplay. As Good As It Gets received seven Oscar nominations, including Best Picture. Notably, Nicholson and Hunt won the Best Actor and Best Actress Oscars, making As Good As It Gets one of the few non-Titanic films that year to win a major Oscar.

As Good As It Gets
PG-13Romantic ComedyDrama Release Date December 25, 1997 Cast Jack Nicholson , Helen Hunt , Greg Kinnear , Cuba Gooding Jr , Shirley Knight Runtime 139 minutes

Watch on MGM+

13 'Shakespeare In Love' (1998)

Director: John Madden

Part historical fiction and part rom-com, Shakespeare in Love stars Gwyneth Paltrow, Joseph Fiennes, Ben Affleck, Geoffrey Rush, and Judi Dench. The film tells the story of the blossoming romance between a young William Shakespeare and Viola de Lesseps, a beautiful woman who dreams of performing on stage.

It's impossible to talk about Shakespeare in Love without acknowledging the ugly role a certain disgraced produced played in its Oscar success. Indeed, the film conducted the Oscar campaign to end all Oscar campaigns, and its efforts paid off. Shakespeare in Love received thirteen Oscar nominations and won seven, including Best Picture. Over the years, its wins have aged like milk, but the film remains a charming and vibrant feel-good movie and a superior entry into the romantic comedy genre.

Shakespeare in Love
RComedyDramaHistoryRomance

The world's greatest ever playwright, William Shakespeare, is young, out of ideas and short of cash, but meets his ideal woman and is inspired to write one of his most famous plays.

Release Date January 29, 1998 Cast Geoffrey Rush , Tom Wilkinson , Steven O'Donnell , Tim McMullan , Joseph Fiennes , Steven Beard Runtime 122

Watch on Max

14 'Silver Linings Playbook' (2012)

Director: David O. Russell

Bradley Cooper and Jennifer Lawrence became bonafide A-listers thanks to the 2012 rom-com Silver Linings Playbook. The film follows the unlikely relationship between Pat, a man with bipolar disorder recently released from a facility, and Tiffany, a young widow. As they rehearse to partake in a dance competition, Pat and Tiffany grow closer.

Critically acclaimed and commercially successful, Silver Linings Playbook was a major player throughout the 2013 awards season. It received eight Oscar nominations, including every major acting category and the Big Five. And while it only prevailed in Best Actress, making Lawrence the second-youngest winner in the category, its legacy as a beloved and revered rom-com is all but ensured.

Silver Linings Playbook
RComedyDocumentaryDramaRomance

After a stint in a mental institution, former teacher Pat Solitano moves back in with his parents and tries to reconcile with his ex-wife. Things get more challenging when Pat meets Tiffany, a mysterious girl with problems of her own.

Release Date September 8, 2012 Cast Jennifer Lawrence , Robert De Niro , Bradley Cooper , Julia Stiles , Chris Tucker , Shea Whigham Runtime 122

Watch on Netflix

NEXT: Rom-Coms That Are More Drama Than Comedy

ncG1vNJzZmibn6G5qrDEq2Wcp51kr6a%2F02apqKWTpLpuuc6voJ6rXaLCrcDIqaOeZZGYrqWxzLJkmq%2BRp7G0edaipaedoqh8

 Share!