Best of Older Women - Younger Men/Boy Romance in Movies

by lankalion | created - 03 Jun 2011 | updated - 13 Dec 2015 | Public

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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1. 40 Carats (1973)

PG | 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: 569

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.

2. A Tiger's Tale (1987)

R | 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

Votes: 464

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.

3. Being Julia (2004)

R | 104 min | Comedy, Drama, Romance

65 Metascore

Set in '30s London, the film involves stage actors and their experiences with love and revenge.

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

Votes: 11,603 | 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.

4. Belle maman (1999)

102 min | Comedy

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

Votes: 818

5. Big (1988)

PG | 104 min | Comedy, Drama, Fantasy

73 Metascore

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: 181,317 | 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.

6. Breakfast at Tiffany's (1961)

Not Rated | 115 min | Comedy, Drama, Romance

76 Metascore

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

Votes: 152,889

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.

7. Bull Durham (1988)

R | 108 min | Comedy, Romance, Sport

73 Metascore

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: 44,145 | 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.

8. Chéri (2009)

R | 86 min | Comedy, Drama, Romance

63 Metascore

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: 10,083 | 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.

9. Class (1983)

R | 98 min | Comedy, Drama, Romance

33 Metascore

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.

Director: Lewis John Carlino | Stars: Jacqueline Bisset, Rob Lowe, Andrew McCarthy, Cliff Robertson

Votes: 8,880

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.

10. Cougar Club (2007)

R | 93 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

Votes: 3,271

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.

11. Crush (I) (2001)

R | 108 min | Comedy, Romance, Drama

37 Metascore

Three female friends behave badly.

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

Votes: 3,523 | 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.

12. Diva (1981)

R | 117 min | Thriller

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

Director: Jean-Jacques Beineix | Stars: Wilhelmenia Fernandez, Frédéric Andréi, Richard Bohringer, Thuy An Luu

Votes: 10,974 | 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.

13. The Door in the Floor (2004)

R | 111 min | Comedy, Drama

67 Metascore

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: 14,770 | 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.

14. The Private Lives of Elizabeth and Essex (1939)

Approved | 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

Votes: 4,614

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.

15. Sunset Blvd. (1950)

Not Rated | 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

Votes: 182,109

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.

16. Far from Heaven (2002)

PG-13 | 107 min | Drama

84 Metascore

In 1950s Connecticut, a 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: 41,567 | 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.

17. The Good Girl (2002)

R | 93 min | Drama, Romance

71 Metascore

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: 41,549 | 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.

18. The Graduate (1967)

PG | 106 min | Comedy, Drama, Romance

83 Metascore

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: 239,806 | 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).

19. Harold and Maude (1971)

PG | 91 min | Comedy, Drama, Romance

62 Metascore

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

Votes: 65,898

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).

20. Heading South (2005)

Unrated | 108 min | Drama

73 Metascore

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: 2,605 | 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.

21. How Stella Got Her Groove Back (1998)

R | 124 min | Comedy, Drama, Romance

56 Metascore

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 ... See full summary »

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

Votes: 6,392 | 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 Terry McMillan's bestselling novel by the same title. The original music score was composed by Michel Colombier.

22. I Could Never Be Your Woman (2007)

PG-13 | 97 min | Comedy, Drama, Romance

A mother falls for a younger man while her daughter falls in love for the first time. Mother Nature messes with their fates.

Director: Amy Heckerling | Stars: Michelle Pfeiffer, Paul Rudd, Saoirse Ronan, Tracey Ullman

Votes: 16,353

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.

23. Impromptu (1991)

PG-13 | 107 min | Biography, Comedy, Music

In 1830s France, pianist/composer Frédéric Chopin is pursued romantically by the determined, individualistic woman who uses the name George Sand.

Director: James Lapine | Stars: Judy Davis, Hugh Grant, Mandy Patinkin, Bernadette Peters

Votes: 4,423 | Gross: $4.08M

24. In Praise of Older Women (1978)

R | 110 min | Comedy, Drama, Romance

Andras 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 ... See full summary »

Director: George Kaczender | Stars: Tom Berenger, Karen Black, Susan Strasberg, Helen Shaver

Votes: 562

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.

25. In the Bedroom (2001)

R | 130 min | Crime, Drama

86 Metascore

A New England couple's college-aged son dates an older woman who has two small children and an unwelcome ex-husband.

Director: Todd Field | Stars: Tom Wilkinson, Sissy Spacek, Nick Stahl, Marisa Tomei

Votes: 35,539 | Gross: $35.93M

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.

26. Life as a House (2001)

R | 125 min | Drama

45 Metascore

When a man is diagnosed with terminal cancer, he takes custody of his misanthropic teenage son, for whom quality time means getting high, engaging in small-time prostitution, and avoiding his father.

Director: Irwin Winkler | Stars: Hayden Christensen, Kevin Kline, Kristin Scott Thomas, Jena Malone

Votes: 41,817 | Gross: $15.65M

Life as a House is a 2001 American drama film produced and directed by Irwin Winkler. The screenplay by Mark Andrus focuses on a man who is anxious to repair his relationship with his ex-wife and teenaged son after he is diagnosed with terminal cancer.

27. Losin' It (1983)

R | 100 min | Comedy, Drama

51 Metascore

Set in 1965, four rowdy teenage guys travel to Tijuana, Mexico for a night of partying when they are joined by a heartbroken housewife who is in town seeking a quick divorce.

Director: Curtis Hanson | Stars: Tom Cruise, Jackie Earle Haley, John Stockwell, John P. Navin Jr.

Votes: 3,803 | Gross: $1.25M

28. Lover Boy (1989)

58 min | Drama

Explores the conflicting worlds of a teenager and a mature woman as they discover the full force of their sexuality.

Director: Geoffrey Wright | Stars: Noah Taylor, Gillian Jones, Ben Mendelsohn, Alice Garner

Votes: 127

Lover Boy is a 1989 film directed by Geoffrey Wright. It stars Noah Taylor and Gillian Jones.

29. The Love Letter (1999)

PG-13 | 88 min | Comedy, Drama, Romance

The power of words and images to open hearts. Helen runs, miles a day, to burn off energy: she's an emotional celibate. Going through the post at her shop, she finds a romantic and poetic ... See full summary »

Director: Peter Ho-Sun Chan | Stars: Kate Capshaw, Tom Everett Scott, Tom Selleck, Blythe Danner

Votes: 3,903 | Gross: $8.28M

The Love Letter is a 1999 American romantic comedy film directed by Peter Chan and starring Kate Capshaw. It is based on the novel by Cathleen Schine. The original music score was composed by Luis Enriquez Bacalov. The film takes place in the New England town of Loblolly-by-the-Sea.

30. Lovely & Amazing (2001)

R | 91 min | Comedy, Drama, Romance

75 Metascore

Self-esteem and insecurity are at the heart of this comedy about the relationship between a mother and her three confused daughters.

Director: Nicole Holofcener | Stars: Catherine Keener, Brenda Blethyn, Troy Ruptash, Emily Mortimer

Votes: 6,579 | Gross: $4.19M

Lovely & Amazing is a 2001 American dramedy film written and directed by Nicole Holofcener.

31. Meeting Venus (1991)

PG-13 | 119 min | Comedy, Drama, Romance

A deliciously biting satire about both the world of Grand Opera and United Europe. A Hungarian conductor (Arestrup) attempts to mount a bold new production of Richard Wagner's "Tannhäuser" ... See full summary »

Director: István Szabó | Stars: Glenn Close, Niels Arestrup, Kiri Te Kanawa, René Kollo

Votes: 1,149 | Gross: $1.00M

Meeting Venus is a 1991 British–American-Japanese film directed by the Hungarian director István Szabó and starring Glenn Close, Niels Arestrup, Marián Labuda, Victor Poletti, Jay O. Sanders, Maria de Medeiros and Johanna ter Steege. The movie was filmed in Budapest, Hungary.

32. The Mother (2003)

R | 112 min | Drama, Romance

72 Metascore

A woman has a passionate affair with a man half her age, who is also sleeping with her daughter.

Director: Roger Michell | Stars: Anne Reid, Daniel Craig, Anna Wilson-Jones, Peter Vaughan

Votes: 3,801 | Gross: $1.06M

The Mother is a 2003 British film directed by Roger Michell.

33. A Night in Heaven (1983)

R | 83 min | Drama, Romance

A married college professor begins a torrid affair with her failing student, who secretly moonlights as a late-night strip-club dancer.

Director: John G. Avildsen | Stars: Christopher Atkins, Lesley Ann Warren, Robert Logan, Deborah Rush

Votes: 1,084 | Gross: $5.56M

A Night in Heaven is a 1983 romance film directed by John G. Avildsen, starring Christopher Atkins as a college student and Lesley Ann Warren as his professor. The screenplay is written by Joan Tewkesbury. Film critics widely panned the movie.

34. Notes on a Scandal (2006)

R | 92 min | Crime, Drama, Romance

73 Metascore

A veteran high school teacher befriends a younger art teacher, who is having an affair with one of her 15-year-old students. However, her intentions with this new "friend" also go well beyond platonic friendship.

Director: Richard Eyre | Stars: Cate Blanchett, Judi Dench, Andrew Simpson, Tom Georgeson

Votes: 71,498 | Gross: $17.51M

Notes on a Scandal is a 2006 psychological thriller film, adapted from the 2003 novel of the same name by Zoë Heller. The screenplay was written by Patrick Marber and the film was directed by Richard Eyre. Many parts of the film were shot in Islington Arts and Media School. The soundtrack was composed by Philip Glass. It was nominated for four Academy Awards – Best Actress, Best Supporting Actress, Best Adapted Screenplay, and Best Original Score.

35. P.S. (2004)

R | 97 min | Comedy, Drama, Fantasy

55 Metascore

An unfulfilled divorced woman gets the chance to relive her past when she meets a young man who appears to be her high school sweetheart who died many years before.

Director: Dylan Kidd | Stars: Laura Linney, Topher Grace, Marcia Gay Harden, Gabriel Byrne

Votes: 5,805 | Gross: $0.18M

p.s. is a 2004 drama film directed by Dylan Kidd. The screenplay by Kidd and Helen Schulman is based on Schulman's 2001 novel P.S. I Love You So Damn Much. The film stars Laura Linney and Topher Grace.

36. The Pallbearer (1996)

PG-13 | 98 min | Comedy, Romance

A young man's life is thrown into a loop when he is asked to be a pallbearer for the funeral of a classmate he doesn't remember, and his old high school crush temporarily returns to town.

Director: Matt Reeves | Stars: David Schwimmer, Gwyneth Paltrow, Michael Rapaport, Toni Collette

Votes: 7,413 | Gross: $5.61M

The Pallbearer is a 1996 American romantic comedy film starring David Schwimmer, Gwyneth Paltrow, Toni Collette, Michael Vartan, Michael Rapaport, and Barbara Hershey. It was screened in the Un Certain Regard section at the 1996 Cannes Film Festival.[

37. Prime (2005)

PG-13 | 105 min | Comedy, Drama, Romance

58 Metascore

A career driven professional from Manhattan is wooed by a young painter, who also happens to be the son of her psychoanalyst.

Director: Ben Younger | Stars: Uma Thurman, Meryl Streep, Bryan Greenberg, Jon Abrahams

Votes: 38,344 | Gross: $22.83M

Prime is a 2005 American romantic comedy film starring Uma Thurman, Meryl Streep and Bryan Greenberg. It was written and directed by Ben Younger. The film has grossed $67,937,503 worldwide.

38. Private Lessons (1981)

R | 87 min | Comedy

34 Metascore

An immigrant housemaid seduces a 15-year-old boy and later fakes her own death as part of his chauffeur's blackmail plot. Troubles arise when the two start to fall in love.

Director: Alan Myerson | Stars: Sylvia Kristel, Howard Hesseman, Eric Brown, Patrick Piccininni

Votes: 3,004 | Gross: $26.28M

Private Lessons is the title of an American comedy film released in 1980. The film starred Sylvia Kristel, Howard Hesseman, Eric Brown, and Ed Begley, Jr. The screenplay was written by Dan Greenburg, who wrote the original source novel, Philly. Greenburg appears as the manager of a fleabag motel in the film. Released in 1981, Private Lessons was highly controversial from the time of its release, for its plot line of a sexual relationship between a boy in his early teens and his 30-something housekeeper. It was one of Kristel's few major American film appearances; she was best known for her Emmanuelle films in Europe. In early 2006, a 25th anniversary DVD release was issued in North America.

39. The Rebound (2009)

R | 95 min | Comedy, Romance

In New York City, a single mom captivates her new neighbor, a much younger man.

Director: Bart Freundlich | Stars: Catherine Zeta-Jones, Justin Bartha, Andrew Cherry, Kelly Gould

Votes: 44,363

The Rebound is a 2009 romantic comedy film directed by Bart Freundlich, starring Catherine Zeta-Jones and Justin Bartha. The film was released in theaters in several countries in late 2009. The film's release in the United States was on 25 December 2010.

40. The Reader (2008)

R | 124 min | Drama, Romance

58 Metascore

Post-WWII Germany: Nearly a decade after his affair with an older woman came to a mysterious end, law student Michael Berg re-encounters his former lover as she defends herself in a war-crime trial.

Director: Stephen Daldry | Stars: Kate Winslet, Ralph Fiennes, Bruno Ganz, Jeanette Hain

Votes: 219,166 | Gross: $34.19M

The Reader is a 2008 drama film based on the 1995 German novel of the same name by Bernhard Schlink. The film was written by David Hare and directed by Stephen Daldry. Ralph Fiennes and Kate Winslet star along with the young actor David Kross. It was the last film for producers Anthony Minghella and Sydney Pollack, who both died before it was released. Production began in Germany in September 2007, and the film opened in limited release on December 10, 2008.

41. Rushmore (1998)

R | 93 min | Comedy, Drama

86 Metascore

The extracurricular king of Rushmore Preparatory School is put on academic probation.

Director: Wes Anderson | Stars: Jason Schwartzman, Bill Murray, Olivia Williams, Seymour Cassel

Votes: 158,388 | Gross: $17.11M

Rushmore is a 1998 comedy-drama film directed by Wes Anderson about an eccentric teenager named Max Fischer (Jason Schwartzman), his friendship with rich industrialist Herman Blume (Bill Murray), and their mutual love for elementary school teacher Rosemary Cross (Olivia Williams). The film was co-written by Anderson and Owen Wilson. The soundtrack was scored by regular Anderson collaborator Mark Mothersbaugh and features several songs by bands associated with the British Invasion of the 1960s.

42. Sanky Panky (2007)

110 min | Comedy, Musical

Genaro gets a job at a resort in hopes of marrying an American woman and moving to New York in search of a better life. He meets a tourist called Martha and everything seems going according to plan, until her boyfriend shows up.

Director: José Enrique Pintor | Stars: Fausto Mata, Zdenka Kalina, Tony Pascual, Aquiles Correa

Votes: 465

Sanky Panky is a 2007 Dominican Republic comedy film directed by José Enrique "Pinky" Pintor. The film was produced entirely in the Dominican Republic and highlighted issues about the Dominican diaspora, The film was shown at the 24th Chicago Latino Film Festival in 2008.

43. Something's Gotta Give (2003)

PG-13 | 128 min | Comedy, Drama, Romance

66 Metascore

A swinger on the cusp of being a senior citizen with a taste for young women falls in love with an accomplished woman closer to his age.

Director: Nancy Meyers | Stars: Jack Nicholson, Diane Keaton, Keanu Reeves, Amanda Peet

Votes: 104,402 | Gross: $124.73M

Something's Gotta Give is a 2003 American romantic comedy film written, produced and directed by Nancy Meyers for both Columbia Pictures and Warner Bros. It stars Jack Nicholson and Diane Keaton as a successful 60-something and 50-something, who find love for each other at a different time of life, despite being complete opposites. Keanu Reeves and Amanda Peet co-star, with Frances McDormand, Paul Michael Glaser, Jon Favreau and KaDee Strickland playing key supporting roles.

44. Summer of '42 (1971)

PG | 104 min | Comedy, Drama, Romance

During his summer vacation on Nantucket Island in 1942, a youth eagerly awaiting his first sexual encounter finds himself developing an innocent love for a young woman awaiting news on her soldier husband's fate in WWII.

Director: Robert Mulligan | Stars: Jennifer O'Neill, Gary Grimes, Jerry Houser, Oliver Conant

Votes: 6,635

Summer of '42 is a 1971 American coming of age drama film based on the memoirs of screenwriter Herman Raucher. It tells the story of Raucher as a boy, in his early teens on his 1942 summer vacation on Nantucket Island, off the coast of New England, who embarked on a one-sided romance with a woman, Dorothy, whose husband had gone off to fight in World War II.

45. Tazza: The High Rollers (2006)

139 min | Comedy, Crime

77 Metascore

A guy with a talent for cards makes his way into the dangerous world of underground gambling in this crime thriller from South Korea. Go-ni (Jo Seung-woo) is a small-town guy with a big ... See full summary »

Director: Dong-hoon Choi | Stars: Seung-woo Cho, Yun-shik Baek, Hye-su Kim, Hae-jin Yoo

Votes: 1,726

Tazza: The High Rollers (a.k.a. The War of Flower, Korean: 타짜) is a 2006 South Korean film based on Huh Young-man's manhwa (comics). The story involves a group of grifters involved in the Korean card game called Hwatu (Korean: 화투, Hanja: 花鬪).

46. Tadpole (2002)

PG-13 | 78 min | Comedy, Drama, Romance

71 Metascore

Coming-of-age story about a suave 15-year-old prep school student who falls in love with his stepmother. When her best friend responds to his advances, he suddenly finds himself in way over his head.

Director: Gary Winick | Stars: Sigourney Weaver, Aaron Stanford, Kate Mara, Robert Iler

Votes: 5,554 | Gross: $2.88M

Tadpole is a 2002 American romantic comedy film directed by Gary Winick and written by Heather McGowan and Niels Mueller. It stars Sigourney Weaver, Bebe Neuwirth, Aaron Stanford, John Ritter, Robert Iler, and Kate Mara. The main character (played by Aaron Stanford) frequently breaks the fourth wall throughout the film.

47. Tim (1979)

Not Rated | 109 min | Drama, Romance

A somewhat mentally handicapped 20-year-old man works as a laborer, but everyone abuses his naiveté. A nice 40-year-old American woman hires him one day and they become close. However, the town and his family see her as predatory.

Director: Michael Pate | Stars: Piper Laurie, Mel Gibson, Alwyn Kurts, Pat Evison

Votes: 2,923

Tim is an Australian romantic drama film. Released in 1979, it was written and directed by Michael Pate, based on the 1974 novel by Colleen McCullough. It is the story of the developing relationship between an older woman named Mary (played by Piper Laurie) and a younger man named Tim (played by Mel Gibson) who has a developmental disability.

48. Water for Elephants (2011)

PG-13 | 120 min | Drama, Romance