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This is a list of mainstream films featuring significant 'May–December' romances, where the age differential between the two adults is wide enough to risk social disapproval. In some of the films listed below, the age difference is a major part of the film plot.


110 min
|

Comedy, Romance


Forty year old Norwegian-American divorcée Ann Stanley owns her own Manhattan based real estate agency specializing in upscale Manhattan apartments. She lives with her seventeen year old ... See full summary »


Director:
Milton Katselas
|
Stars:
Liv Ullmann ,
Edward Albert ,
Gene Kelly ,
Binnie Barnes


Votes:
744
| Gross:
$2.50M

Forty Carats is a 1973 American film directed by Milton Katselas, based on the play by Jay Presson Allen. The screenplay was written by Leonard Gershe (who significantly changed the ending) and directed by Milton Katselas. The cast include Liv Ullman, Edward Albert, Gene Kelly, Binnie Barnes, Deborah Raffin, Nancy Walker, and Natalie Schafer. Ullman was nominated for a Golden Globe as Best Motion Picture Actress, Musical or Comedy, and the Writers Guild of America nominated Gershe's screenplay for Best Comedy Adapted from Another Medium.


97 min
|

Comedy, Drama


A young man falls for his girlfriend's mother.

Director:
Peter Douglas
|
Stars:
Ann-Margret ,
C. Thomas Howell ,
Charles Durning ,
Kelly Preston

A Tiger's Tale is a 1987 film written and directed by Peter Douglas, based on the novel Love and Other Natural Disasters by Allen Hannay III.

R
|
104 min
|

Comedy, Drama, Romance


Set in 1930s London, this movie involves stage actors and actresses and their experiences with love and revenge.

Director:
István Szabó
|
Stars:
Annette Bening ,
Michael Gambon ,
Maury Chaykin ,
Jeremy Irons


Votes:
12 268
| Gross:
$7.74M

Being Julia is a 2004 drama film with comic undertones directed by István Szabó and starring Annette Bening and Jeremy Irons. The screenplay by Ronald Harwood is based on the 1937 novel Theatre by W. Somerset Maugham. The original music score is composed by Mychael Danna.

On his wedding day, Antoine falls madly in love with Léa, his mother-in-law.

Director:
Gabriel Aghion
|
Stars:
Catherine Deneuve ,
Vincent Lindon ,
Mathilde Seigner ,
Line Renaud



104 min
|

Comedy, Drama, Fantasy


After wishing to be made big, a teenage boy wakes the next morning to find himself mysteriously in the body of an adult.

Director:
Penny Marshall
|
Stars:
Tom Hanks ,
Elizabeth Perkins ,
Robert Loggia ,
John Heard


Votes:
207 542
| Gross:
$114.97M

Big is a 1988 romantic comedy film directed by Penny Marshall and stars Tom Hanks as Josh Baskin, a young boy who makes a wish "to be big" to a magical fortune-telling machine and is then aged to adulthood overnight. The film also stars Elizabeth Perkins, and Robert Loggia and was written by Gary Ross, with Justin Schindler and Anne Spielberg. The story was heavily inspired by, though not an actual remake of, the 1987 Italian film Da grande.


115 min
|

Comedy, Drama, Romance


A young New York socialite becomes interested in a young man who has moved into her apartment building, but her past threatens to get in the way.

Director:
Blake Edwards
|
Stars:
Audrey Hepburn ,
George Peppard ,
Patricia Neal ,
Buddy Ebsen

Breakfast at Tiffany's is a 1961 romantic comedy film starring Audrey Hepburn and George Peppard, and featuring Patricia Neal, Buddy Ebsen, Martin Balsam, and Mickey Rooney. The film was directed by Blake Edwards and released by Paramount Pictures. It was loosely based on the novella of the same name by Truman Capote.
Hepburn's portrayal of Holly Golightly as the naïve, eccentric woman is generally considered to be the actress' most memorable and identifiable role. She herself regarded it as one of her most challenging roles, since she was an introvert required to play an extrovert. Hepburn's performance of "Moon River" helped composer Henry Mancini and lyricist Johnny Mercer win an Oscar for Best Song.


108 min
|

Comedy, Romance, Sport


A fan who has an affair with one minor-league baseball player each season meets an up-and-coming pitcher and the experienced catcher assigned to him.

Director:
Ron Shelton
|
Stars:
Kevin Costner ,
Susan Sarandon ,
Tim Robbins ,
Trey Wilson


Votes:
51 269
| Gross:
$50.89M

Bull Durham is a 1988 American romantic comedy film about baseball. It is based upon the minor league experiences of writer/director Ron Shelton and depicts the players and fans of the Durham Bulls, a minor league baseball team in Durham, North Carolina.
Kevin Costner stars as "Crash" Davis, a veteran catcher brought in to teach rookie pitcher Ebby Calvin "Nuke" LaLoosh (Tim Robbins) about the game in preparation for reaching the Major Leagues. Baseball groupie Annie Savoy (Susan Sarandon) romances Nuke but finds herself increasingly attracted to Crash. Also featured are Robert Wuhl and Trey Wilson, as well as popular baseball "clown" Max Patkin.

R
|
100 min
|

Comedy, Drama, Romance


The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.

Director:
Stephen Frears
|
Stars:
Michelle Pfeiffer ,
Rupert Friend ,
Kathy Bates ,
Frances Tomelty


Votes:
10 978
| Gross:
$2.71M

Chéri is a 2009 drama film directed by Stephen Frears. Starring Michelle Pfeiffer and Rupert Friend, it is an adaptation of the novel by French author Colette. The film premiered at the 2009 Berlin International Film Festival.


98 min
|

Comedy, Drama, Romance


A young man in private school spends one crazy night out, but soon realizes the woman he hooked up with is not who he expected.
Class is a 1983 American movie that was directed by Lewis John Carlino, the writer/director of the 1979 film The Great Santini. It features the film debuts of actors Andrew McCarthy, John Cusack, Virginia Madsen, Lolita Davidovich, and Alan Ruck.

R
|
97 min
|

Comedy


2 friends graduate college and start at a law firm. Hogan is into cougars. Spence needs his employer's recommendation for Yale Law so being with his wife isn't smart. He helps Hogan start Cougar Club.

Director:
Christopher Duddy
|
Stars:
Jason Jurman ,
Warren Kole ,
Joe Mantegna ,
Kaley Cuoco

Cougar Club is a 2007 American film directed by Christopher Duddy. The film details the attempts of two college graduates, Marshall Hogan III and Spence Holmes, to find direction in life. While working as interns for abusive divorce lawyers, they come up with a plan to make money from the passion that is Hogan's pride and Spence's secret desire: having sex with Cougars — older women looking to have sex with younger men. Some of the "cougars" are played by actresses such as Faye Dunaway and Carrie Fisher.

R
|
108 min
|

Comedy, Drama, Romance


Director:
John McKay
|
Stars:
Andie MacDowell ,
Imelda Staunton ,
Anna Chancellor ,
Kenny Doughty


Votes:
3 744
| Gross:
$1.08M

Crush is a 2001 film written and directed by John McKay and starring Andie MacDowell, Imelda Staunton, Anna Chancellor, Kenny Doughty, and Bill Paterson.


117 min
|

Music, Thriller


Two tapes, two Parisian mob killers, one corrupt policeman, an opera fan, a teenage thief, and the coolest philosopher ever filmed all twist their way through an intricate and stylish French-language thriller.

Votes:
12 471
| Gross:
$0.11M

Diva is a 1981 film directed by Jean-Jacques Beineix, adapted from a novel of the same name by Daniel Odier (under the pseudonym Delacorta). It is one of the first French films to let go of the realist, harsh mood of 1970s French cinema and return to a colourful, melodic style, called cinema du look. The film made a muted debut in France in 1981, but had success in the United States the next year. The film became a cult classic and was internationally acclaimed.

R
|
111 min
|

Comedy, Drama


A writer's young assistant becomes both pawn and catalyst in his boss's disintegrating household.

Director:
Tod Williams
|
Stars:
Jeff Bridges ,
Kim Basinger ,
Jon Foster ,
Elle Fanning


Votes:
15 466
| Gross:
$3.84M

The Door in the Floor is a 2004 American drama film written and directed by Tod Williams. The screenplay is based on the first third of the 1998 novel A Widow for One Year by John Irving.


106 min
|

Biography, Drama, History


A depiction of the love/hate relationship between Queen Elizabeth I and Robert Devereux, the Earl of Essex.

Director:
Michael Curtiz
|
Stars:
Bette Davis ,
Errol Flynn ,
Olivia de Havilland ,
Donald Crisp

The Private Lives of Elizabeth and Essex (1939) is a historical romantic drama film. It is based on the relationship between Queen Elizabeth I, portrayed by Bette Davis, and Robert Devereux, 2nd Earl of Essex, played by Errol Flynn. The film was directed by Michael Curtiz, and was based on the Maxwell Anderson play, Elizabeth the Queen, which had been successful on Broadway with Lynn Fontanne and Alfred Lunt in the lead roles. The supporting cast included Olivia de Havilland, Donald Crisp, Henry Daniell, Henry Stephenson, and Vincent Price. The score was composed by Erich Wolfgang Korngold, who later used a theme from the film in his Symphony in F sharp major. The Technicolor cinematography was by Sol Polito, and the elaborate costumes were designed by Orry-Kelly.


110 min
|

Drama, Film-Noir


A screenwriter develops a dangerous relationship with a faded film star determined to make a triumphant return.

Director:
Billy Wilder
|
Stars:
William Holden ,
Gloria Swanson ,
Erich von Stroheim ,
Nancy Olson

Sunset Boulevard (also known as Sunset Blvd.) is a 1950 American film noir directed and co-written by Billy Wilder, and produced and co-written by Charles Brackett. It was named after the boulevard that runs through Los Angeles and Beverly Hills, California.
The film stars William Holden as an unsuccessful screenwriter, Gloria Swanson as a faded silent movie star who draws him into her fantasy world, in which she dreams of making a triumphant return to the screen and Erich von Stroheim as her butler. Nancy Olson, Fred Clark, Lloyd Gough and Jack Webb play supporting roles. Director Cecil B. DeMille and gossip columnist Hedda Hopper play themselves, and the film includes cameo appearances by leading silent film actors Buster Keaton, H. B. Warner and Anna Q. Nilsson.

PG-13
|
107 min
|

Drama, Romance


In 1950s Connecticut, a flustered housewife faces a marital crisis and mounting racial tensions in the outside world.

Director:
Todd Haynes
|
Stars:
Julianne Moore ,
Dennis Quaid ,
Dennis Haysbert ,
Patricia Clarkson


Votes:
45 349
| Gross:
$15.85M

Far from Heaven is a 2002 drama film written and directed by Todd Haynes and starring Julianne Moore, Dennis Quaid, Dennis Haysbert, and Patricia Clarkson.
The film tells the story of Cathy Whitaker, a 1950s housewife, living in suburban Hartford as she sees her seemingly perfect life begin to fall apart. It is done in the style of a Douglas Sirk film (especially 1955's All That Heaven Allows and 1959's Imitation of Life), dealing with complex contemporary issues such as race, gender roles, sexual orientation and class.

R
|
93 min
|

Drama, Romance


A discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.

Director:
Miguel Arteta
|
Stars:
Jennifer Aniston ,
Jake Gyllenhaal ,
Deborah Rush ,
Mike White


Votes:
44 277
| Gross:
$14.02M

The Good Girl is a 2002 black comedy-drama film directed by Miguel Arteta from a script by Mike White, and stars Jennifer Aniston, Jake Gyllenhaal and John C. Reilly.

PG
|
106 min
|

Comedy, Drama, Romance


A disillusioned college graduate finds himself torn between his older lover and her daughter.

Director:
Mike Nichols
|
Stars:
Dustin Hoffman ,
Anne Bancroft ,
Katharine Ross ,
William Daniels


Votes:
262 330
| Gross:
$104.95M

The Graduate is a 1967 American romantic-comedy motion picture directed by Mike Nichols. It is based on the 1963 novel The Graduate by Charles Webb, who wrote it shortly after graduating from Williams College. The screenplay was by Buck Henry, who makes a cameo appearance as a hotel clerk, and Calder Willingham. The film tells the story of Benjamin Braddock (played by Dustin Hoffman), a recent university graduate with no well-defined aim in life, who is seduced by an older woman, Mrs. Robinson (Anne Bancroft), and then proceeds to fall in love with her daughter Elaine (Katharine Ross).


91 min
|

Comedy, Drama, Romance


Young, rich, and obsessed with death, Harold finds himself changed forever when he meets lively septuagenarian Maude at a funeral.

Director:
Hal Ashby
|
Stars:
Ruth Gordon ,
Bud Cort ,
Vivian Pickles ,
Cyril Cusack

Harold and Maude is a 1971 American comedy film directed by Hal Ashby and released by Paramount Pictures. It incorporates elements of dark humor and existentialist drama, with a plot that revolves around the exploits of a young man intrigued with death, Harold (played by Bud Cort). Harold drifts away from the life that his detached mother prescribes for him, and develops a relationship with an old woman named Maude (played by Ruth Gordon).

Three female tourists have their eyes opened while visiting the poverty-stricken and dangerous world of 1980s Haiti.

Director:
Laurent Cantet
|
Stars:
Charlotte Rampling ,
Karen Young ,
Louise Portal ,
Ménothy Cesar


Votes:
2 765
| Gross:
$0.90M

Heading South (French: Vers Le Sud) is a 2005 French drama film by director Laurent Cantet and based on three short stories by Dany Laferrière, it depicts the experiences of three middle-aged white women in the late 1970s, traveling to Haiti for the purposes of sexual tourism with young black men. Their adventures (as seen in their eyes) are juxtaposed to class issues and the deteriorating political climate of Haiti at the time. The women demonstrate different attitudes to the complex situation.

R
|
124 min
|

Comedy, Drama, Romance


Stella is a highly successful, forty-something San Francisco stock broker who is persuaded by her colorful New York girlfriend Delilah to take a well deserved, first-class vacation to Jamaica.

Director:
Kevin Rodney Sullivan
|
Stars:
Angela Bassett ,
Taye Diggs ,
Whoopi Goldberg ,
Regina King


Votes:
7 329
| Gross:
$37.67M

How Stella Got Her Groove Back is a 1998 romance film, directed by Kevin Rodney Sullivan. The film stars Angela Bassett, Taye Diggs, Whoopi Goldberg and Regina King. This film is an adaptation of
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