Gidget and Geezer
by Art Snob | created - 08 Aug 2018 | updated - 2 months ago | PublicWhen it comes to wish-fulfillment fantasies, Hollywood has long provided hope (where none exists) for the possibility of an unlikely romance – a beautiful girl somehow falling for an awkward loser or a guy old enough to be her father. Are you in the latter category and in need of such hope? Here are the films that will provide it!
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1. To Have and Have Not (1944)
PG | 100 min | Adventure, Comedy, Film-Noir
During World War II, American expatriate Harry Morgan helps transport a French Resistance leader and his beautiful wife to Martinique while romancing a sensuous lounge singer.
Director: Howard Hawks | Stars: Humphrey Bogart, Lauren Bacall, Walter Brennan, Dolores Moran
Votes: 30,031
Humphrey Bogart 45, Lauren Bacall 20
2. Sabrina (1954)
G | 113 min | Comedy, Drama, Romance
A playboy becomes interested in the daughter of his family's chauffeur, but it's his more serious brother who would be the better man for her.
Director: Billy Wilder | Stars: Humphrey Bogart, Audrey Hepburn, William Holden, Walter Hampden
Votes: 57,247
Humphrey Bogart 55, Audrey Hepburn 25
3. Love in the Afternoon (1957)
PG | 130 min | Comedy, Crime, Drama
A middle-aged playboy becomes fascinated by the daughter of a private detective who has been hired to entrap him with the wife of a client.
Director: Billy Wilder | Stars: Gary Cooper, Audrey Hepburn, Maurice Chevalier, John McGiver
Votes: 13,430
Gary Cooper 56, Audrey Hepburn 28
4. Ten North Frederick (1958)
PG | 102 min | Drama, Romance
At her father's funeral, Ann Chapin thinks back over the last five years of his life, years of apparent political and personal failure dominated by a selfish and dissatisfied wife and eased... See full summary »
Director: Philip Dunne | Stars: Gary Cooper, Diane Varsi, Suzy Parker, Geraldine Fitzgerald
Votes: 586
Gary Cooper 57, Suzy Parker 26
5. Daddy Long Legs (1955)
126 min | Musical, Romance
A wealthy American has a chance encounter with a joyful young French woman, and anonymously pays for her education. She writes letters to her mysterious benefactor, nicknaming him from the description given by some of her fellow orphans.
Director: Jean Negulesco | Stars: Fred Astaire, Leslie Caron, Terry Moore, Thelma Ritter
Votes: 3,393
Fred Astaire 56, Leslie Caron 24
6. Funny Face (1957)
103 min | Comedy, Musical, Romance
An impromptu fashion shoot at a book store brings about a new fashion model discovery in the shop clerk.
Director: Stanley Donen | Stars: Audrey Hepburn, Fred Astaire, Kay Thompson, Michel Auclair
Votes: 25,971
Fred Astaire 58, Audrey Hepburn 28
7. American Beauty (1999)
18A | 122 min | Drama
A sexually frustrated suburban father has a mid-life crisis after becoming infatuated with his daughter's best friend.
Director: Sam Mendes | Stars: Kevin Spacey, Annette Bening, Thora Birch, Wes Bentley
Votes: 1,043,705 | Gross: $130.10M
Kevin Spacey 40, Mena Suvari 20
8. Sense and Sensibility (1995)
PG | 136 min | Drama, Romance
Rich Mr. Dashwood dies, leaving his second wife and her three daughters poor by the rules of inheritance. The two eldest daughters are the title opposites.
Director: Ang Lee | Stars: Emma Thompson, Kate Winslet, James Fleet, Tom Wilkinson
Votes: 98,707 | Gross: $43.18M
Alan Rickman 49, Kate Winslet 20
9. Cactus Flower (1969)
104 min | Comedy, Romance
A dentist pretends to be married to avoid commitment, but when he falls for his girlfriend and proposes, he must recruit his lovelorn nurse to pose as his wife.
Director: Gene Saks | Stars: Walter Matthau, Ingrid Bergman, Goldie Hawn, Jack Weston
Votes: 9,258 | Gross: $25.89M
Walter Matthau 49, Goldie Hawn 24
10. Sin City (2005)
16+ | 124 min | Crime, Thriller
A movie that explores the dark and miserable town, Basin City, tells the story of three different people, all caught up in violent corruption.
Directors: Frank Miller, Robert Rodriguez, Quentin Tarantino | Stars: Mickey Rourke, Clive Owen, Bruce Willis, Jessica Alba
Votes: 731,597 | Gross: $74.10M
Bruce Willis 50, Jessica Alba 24
11. Everyone Says I Love You (1996)
PG | 101 min | Comedy, Musical, Romance
A New York girl sets her father up with a beautiful woman in a troubled marriage while her stepsister gets engaged.
Director: Woody Allen | Stars: Woody Allen, Goldie Hawn, Julia Roberts, Edward Norton
Votes: 34,684 | Gross: $9.71M
Woody Allen 61, Julia Roberts 29
12. Mad Dog and Glory (1993)
R | 97 min | Comedy, Crime, Drama
After his life is saved by a lonely cop, a mobster who moonlights as a stand-up comedian provides the cop with a beautiful young companion.
Director: John McNaughton | Stars: Robert De Niro, Uma Thurman, Bill Murray, David Caruso
Votes: 20,072 | Gross: $11.08M
Robert DeNiro 50, Uma Thurman 23
13. Something's Gotta Give (2003)
PG | 128 min | Comedy, Drama, Romance
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: 109,328 | Gross: $124.73M
Jack Nicholson 66, Amanda Peet 31
14. The Intern (I) (2015)
PG | 121 min | Comedy, Drama
Seventy-year-old widower Ben Whittaker has discovered that retirement isn't all it's cracked up to be. Seizing an opportunity to get back in the game, he becomes a senior intern at an online fashion site, founded and run by Jules Ostin.
Director: Nancy Meyers | Stars: Robert De Niro, Anne Hathaway, Rene Russo, Anders Holm
Votes: 210,443 | Gross: $75.76M
Robert DeNiro 71, Anne Hathaway 33
15. Girl with a Pearl Earring (2003)
PG-13 | 100 min | Biography, Drama, Romance
A young peasant maid working in the house of painter Johannes Vermeer becomes his talented assistant and the model for one of his most famous works.
Director: Peter Webber | Stars: Scarlett Johansson, Colin Firth, Tom Wilkinson, Judy Parfitt
Votes: 70,920 | Gross: $11.63M
Colin Firth 43, Scarlett Johansson 19
16. Blaze (1989)
14A | 120 min | Biography, Drama
A middle-aged Louisiana governor falls in love with a young stripper, which jeopardizes his political career and the radical policies which have made him a controversial figure.
Director: Ron Shelton | Stars: Paul Newman, Lolita Davidovich, Jerry Hardin, Gailard Sartain
Votes: 3,492 | Gross: $19.13M
Paul Newman 64, Lolita Davidovich 28
17. Trois couleurs: Rouge (1994)
14 | 99 min | Drama, Mystery, Romance
A model discovers a retired judge is keen on invading people's privacy.
Director: Krzysztof Kieslowski | Stars: Irène Jacob, Jean-Louis Trintignant, Frédérique Feder, Jean-Pierre Lorit
Votes: 86,820 | Gross: $4.04M
Jean-Louis Trintignant 64, Irene Jacob 28
18. La Belle Noiseuse (1991)
238 min | Drama
The former famous painter Frenhofer revisits an abandoned project using the girlfriend of a young visiting artist. Questions about truth, life, and artistic limits are explored.
Director: Jacques Rivette | Stars: Michel Piccoli, Jane Birkin, Emmanuelle Béart, Marianne Denicourt
Votes: 6,713 | Gross: $0.41M
Michael Piccoli 66, Emanuel Beart 28
19. Entrapment (1999)
PG | 113 min | Action, Crime, Romance
An insurance agent is sent by her employer to track down and help capture an art thief.
Director: Jon Amiel | Stars: Sean Connery, Catherine Zeta-Jones, Ving Rhames, Will Patton
Votes: 104,735 | Gross: $87.70M
Sean Connery 69, Catherine Zeta-Jones 30
20. Shopgirl (2005)
PG | 106 min | Drama, Romance
A film adaptation of Steve Martin's novel about a complex love triangle between a bored salesgirl, a wealthy businessman and an aimless young man.
Director: Anand Tucker | Stars: Steve Martin, Claire Danes, Jason Schwartzman, Bridgette Wilson-Sampras
Votes: 23,077 | Gross: $10.28M
Steve Martin 65, Claire Danes 26
21. Ultimo tango a Parigi (1972)
R | 129 min | Drama, Romance
A young Parisian woman meets a middle-aged American businessman who demands their clandestine relationship be based only on sex.
Director: Bernardo Bertolucci | Stars: Marlon Brando, Maria Schneider, Maria Michi, Giovanna Galletti
Votes: 48,316 | Gross: $36.14M
Marlon Brando 48, Maria Schneider 20
22. Stealing Beauty (1996)
R | 118 min | Drama, Mystery, Romance
After her mother commits suicide, a young woman travels to Italy in search of love, truth and a deeper connection with herself.
Director: Bernardo Bertolucci | Stars: Jeremy Irons, Liv Tyler, Carlo Cecchi, Sinéad Cusack
Votes: 25,303 | Gross: $4.57M
Jeremy Irons 48, Liv Tyler 19
23. Manhattan (1979)
18A | 96 min | Comedy, Drama, Romance
The life of a divorced television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.
Director: Woody Allen | Stars: Woody Allen, Diane Keaton, Mariel Hemingway, Michael Murphy
Votes: 128,420 | Gross: $45.70M
Woody Allen 44, Mariel Hemingway 18
24. La fille de 15 ans (1989)
G | 86 min | Drama, Romance
Father slowly falls in love with his son's teenage girlfriend.
Director: Jacques Doillon | Stars: Judith Godrèche, Melvil Poupaud, Jacques Doillon, Tina Sportolaro
Votes: 307
Jacques Doillon 45, Judith Godrèche 17
25. Age of Consent (1969)
106 min | Biography, Comedy, Drama
A grizzled Australian painter decides to jolt his stale creativity in a remote island on the Great Barrier Reef, where he meets an alluring young islander who becomes his enchanting model. Could the untamed girl be his long-awaited muse?
Director: Michael Powell | Stars: James Mason, Helen Mirren, Jack MacGowran, Neva Carr-Glynn
Votes: 2,781
James Mason 60, Helen Mirren 24
26. Blame It on Rio (1984)
PA | 100 min | Comedy, Romance
Best friends and their daughters vacation in Rio de Janeiro only for one to fall for the other's daughter.
Director: Stanley Donen | Stars: Michael Caine, Michelle Johnson, Demi Moore, Joseph Bologna
Votes: 9,703 | Gross: $18.64M
Michael Caine 51, Michelle Johnson 19
27. Lost in Translation (2003)
14A | 102 min | Comedy, Drama
A faded movie star and a neglected young woman form an unlikely bond after crossing paths in Tokyo.
Director: Sofia Coppola | Stars: Bill Murray, Scarlett Johansson, Giovanni Ribisi, Anna Faris
Votes: 399,638 | Gross: $44.59M
Bill Murray 53, Scarlett Johansson 19
28. My First Mister (2001)
R | 109 min | Comedy, Drama, Romance
A 17-year-old girl has a troubled relationship with a 49-year-old man.
Director: Christine Lahti | Stars: Albert Brooks, Leelee Sobieski, Rutanya Alda, Natasha Braisewell
Votes: 5,346 | Gross: $0.62M
Albert Brooks 54, Leelee Sobieski 18
29. Poison Ivy (1992)
AA | 90 min | Drama, Thriller
A seductive teen befriends an introverted high school student and schemes her way into the lives of her wealthy family.
Director: Katt Shea | Stars: Drew Barrymore, Sara Gilbert, Tom Skerritt, Cheryl Ladd
Votes: 16,838 | Gross: $1.83M
Tom Skerritt 59, Drew Barrymore 17
30. Jeune et jolie (2013)
18A | 95 min | Drama, Romance
After losing her virginity, Isabelle takes up a secret life as a call girl, meeting her clients for hotel-room trysts. Throughout, she remains curiously aloof, showing little interest in the encounters themselves or the money she makes.
Director: François Ozon | Stars: Marine Vacth, Géraldine Pailhas, Frédéric Pierrot, Fantin Ravat
Votes: 31,162 | Gross: $0.05M
Johan Leysen 63, Marine Vacth 22
31. Whatever Works (2009)
PG | 93 min | Comedy, Romance
A middle-aged, misanthropic divorcée from New York City surprisingly enters a fulfilling, Pygmalion-type relationship with a much younger, unsophisticated Southern girl.
Director: Woody Allen | Stars: Evan Rachel Wood, Larry David, Henry Cavill, Adam Brooks
Votes: 69,764 | Gross: $5.31M
Larry David 66, Evan Rachel Wood 22
32. I Love You, Daddy (2017)
R | 123 min | Comedy, Drama
When a successful television writer's daughter becomes the interest of an aging filmmaker with an appalling past, he becomes worried about how to handle the situation.
Director: Louis C.K. | Stars: Louis C.K., Chloë Grace Moretz, Rose Byrne, Charlie Day
Votes: 3,671
John Malkovich 64, Chloë Grace Moretz 20
33. Venus (I) (2006)
R | 95 min | Comedy, Drama, Romance
Life for a pair of veteran actors gets turned upside down after they meet a brash teenager.
Director: Roger Michell | Stars: Peter O'Toole, Jodie Whittaker, Leslie Phillips, Beatrice Savoretti
Votes: 12,224 | Gross: $3.34M
Peter O'Toole 74, Jodie Whitaker 24
34. Like Someone in Love (2012)
109 min | Drama
In Tokyo, a young sex worker develops an unexpected connection with a widower over a period of two days.
Directors: Abbas Kiarostami, Shay Modaressi | Stars: Rin Takanashi, Tadashi Okuno, Ryô Kase, Denden
Votes: 9,808 | Gross: $0.22M
Tadashi Okuno 84, Rin Takanashi 24
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