Best of Older Women - Younger Men/Boy Romance in Movies
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.
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- DirectorMilton KatselasStarsLiv UllmannEdward AlbertGene KellyForty 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 daughter Trina Stanley, and her mother, Maud Ericson, who acts more the teenager than Trina. Largely because of her uptight and regimented attitude, Ann has had no love in her life since divorcing her ex-husband, character actor Billy Boylan, an irresponsible man who she still loves as a friend and who she sees whenever he is in town between acting jobs and whenever he needs money from her. Ann's uptight attitude seems to have softened slightly ever since returning from a trip to Greece with Maud. What she has not told anyone is that her softened attitude is from a romantic one night only liaison with a young American man she met by happenstance by an out of the way Greek beach, he who tried to get her to be more carefree, if only for that one night. Purely by coincidence, she meets that man again in New York. He is twenty-two year old Peter Latham, a steel heir who is an acquaintance of Trina's. While Ann's family and friends encourage her to pursue a relationship with a wealthy southern gentleman client named J.D. Rogers, Peter pursues Ann behind the scenes, while Maud believes Peter wants to court Trina. Peter is falling in love with Ann. Although she admits she is flattered by Peter's declaration, Ann may not be able to get over the difference in their ages, regardless of what she may be feeling about him. If she can let go of that repressed attitude, she may give herself the opportunity to examine if she truly does have romantic feelings for Peter, and what to do about them if they do exist. Dealing with an issue with Trina, discussing Billy's own life with him, and meeting Peter's friends and family may give Ann some insight into the matter.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.
- DirectorPeter DouglasStarsAnn-MargretC. Thomas HowellCharles DurningA young man falls for his girlfriend's mother.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.
- DirectorIstván SzabóStarsAnnette BeningMichael GambonMaury ChaykinSet in 1930s London, this movie involves stage actors and actresses and their experiences with love and revenge.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.
- DirectorGabriel AghionStarsCatherine DeneuveVincent LindonMathilde SeignerOn his wedding day, Antoine falls madly in love with Léa, his mother-in-law.
- DirectorPenny MarshallStarsTom HanksElizabeth PerkinsRobert LoggiaAfter wishing to be made big, a teenage boy wakes the next morning to find himself mysteriously in the body of an adult.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.
- DirectorBlake EdwardsStarsAudrey HepburnGeorge PeppardPatricia NealA 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.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. - DirectorRon SheltonStarsKevin CostnerSusan SarandonTim RobbinsA 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.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. - DirectorStephen FrearsStarsMichelle PfeifferRupert FriendKathy BatesThe 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.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.
- DirectorLewis John CarlinoStarsJacqueline BissetRob LoweAndrew McCarthyA young man in private school spends one crazy night out, and only later does he learn more about the woman who enlivened his night.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.
- DirectorChristopher DuddyStarsJason JurmanWarren KoleJoe Mantegna2 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.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.
- DirectorJohn McKayStarsAndie MacDowellImelda StauntonAnna ChancellorThree 40-something women in a small English town meet weekly for a ritual of gin, cigarettes, and sweets -- and swap stories arguing which of them has the most pathetic love life. Kate is the headmistress at the local school; her best friends are the town's police chief and a cynical, thrice-divorced doctor. When Kate begins a fling with a handsome younger man, less worldly than her friends but passionate and sincere, the other women can't simply be happy for the couple's unusual new romance. In jealousy they promptly take it upon themselves to break up the pair, taking drastic measures which result in unintended outcomes, some happy and some tragic.Crush is a 2001 film written and directed by John McKay and starring Andie MacDowell, Imelda Staunton, Anna Chancellor, Kenny Doughty, and Bill Paterson.
- DirectorJean-Jacques BeineixStarsWilhelmenia FernandezFrédéric AndréiRoland BertinTwo 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.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.
- DirectorTod WilliamsStarsJeff BridgesKim BasingerJon FosterA writer's young assistant becomes both pawn and catalyst in his boss's disintegrating household.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.
- DirectorMichael CurtizStarsBette DavisErrol FlynnOlivia de HavillandA depiction of the love/hate relationship between Queen Elizabeth I and Robert Devereux, the Earl of Essex.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.
- DirectorBilly WilderStarsWilliam HoldenGloria SwansonErich von StroheimA screenwriter develops a dangerous relationship with a faded film star determined to make a triumphant return.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. - DirectorTodd HaynesStarsJulianne MooreDennis QuaidDennis HaysbertIn 1950s Connecticut, a flustered housewife faces a marital crisis and mounting racial tensions in the outside world.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. - DirectorMiguel ArtetaStarsJennifer AnistonJake GyllenhaalDeborah RushA discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.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.
- DirectorMike NicholsStarsDustin HoffmanAnne BancroftKatharine RossA disillusioned college graduate finds himself torn between his older lover and her daughter.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).
- DirectorHal AshbyStarsRuth GordonBud CortVivian PicklesYoung, rich, and obsessed with death, Harold finds himself changed forever when he meets lively septuagenarian Maude at a funeral.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).
- DirectorLaurent CantetStarsCharlotte RamplingKaren YoungLouise PortalThree female tourists have their eyes opened while visiting the poverty-stricken and dangerous world of 1980s Haiti.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.
- DirectorKevin Rodney SullivanStarsAngela BassettTaye DiggsWhoopi GoldbergStella 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.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 Terry McMillan's bestselling novel by the same title. The original music score was composed by Michel Colombier.
- DirectorAmy HeckerlingStarsMichelle PfeifferPaul RuddSaoirse RonanA mother falls for a younger man while her daughter falls in love for the first time. Mother Nature messes with their fates.I Could Never Be Your Woman is a 2007 American romantic comedy film directed and written by Amy Heckerling and starring Michelle Pfeiffer and Paul Rudd.
- DirectorJames LapineStarsJudy DavisHugh GrantMandy PatinkinIn 1830s France, pianist/composer Frédéric Chopin is pursued romantically by the determined, individualistic woman who uses the name George Sand.
- DirectorGeorge KaczenderStarsTom BerengerKaren BlackSusan StrasbergAndras Vajda grows up in a turbulent, war-torn Hungary, where he procures local girls for the occupying G.I.'s during World War II. Disappointed by girls of his age, he meets Maya, a married women in her thirties, who tutors him in the lessons of love and romance. Maya is only the first of many mature women that Andras will meet through his teenage and young adult life.In Praise of Older Women is George Kaczender’s twelfth feature film. It was written by Stephen Vizinczey (novel), Paul Gottlieb and Barrie Wexler. The story happens in Hungary during and after World War II but the movie was shot in Montréal, Canada. The film was premiered at the Toronto Film Festival on September 14, 1978.
- DirectorTodd FieldStarsTom WilkinsonSissy SpacekNick StahlA New England couple's college-aged son dates an older woman who has two small children and an unwelcome ex-husband.In the Bedroom is a 2001 American film directed by Todd Field, and dedicated to Andre Dubus, whose short story Killings is the source material on which the screenplay, by Field and Robert Festinger, is based. The film stars Tom Wilkinson, Sissy Spacek, Nick Stahl, Marisa Tomei and William Mapother.