Sort by Popularity - Most Popular Movies and TV Shows tagged with keyword "older-man-younger-woman-relationship"
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51. Cat Person (I) (2023)
R | 118 min | Drama, Horror, Thriller
When Margot, a college sophomore, goes on a date with the older Robert, she finds that he doesn't live up to the Robert she has been flirting with over texts. A razor-sharp exploration of the horrors of dating.
Director: Susanna Fogel | Stars: Emilia Jones, Nicholas Braun, Geraldine Viswanathan, Isabella Rossellini
Votes: 5,683
52. GLOW (2017–2019)
TV-MA | 35 min | Comedy, Drama, Sport
A look at the personal and professional lives of a group of women who perform for a wrestling organization in Los Angeles during the 1980s.
Stars: Alison Brie, Marc Maron, Betty Gilpin, Britt Baron
Votes: 50,684
53. Licorice Pizza (2021)
R | 133 min | Comedy, Drama, Romance
The story of Alana Kane and Gary Valentine growing up, running around and going through the treacherous navigation of first love in the San Fernando Valley, 1973.
Director: Paul Thomas Anderson | Stars: Alana Haim, Cooper Hoffman, Sean Penn, Tom Waits
Votes: 140,560
54. No Strings Attached (I) (2011)
R | 108 min | Comedy, Romance
A guy and girl try to keep their relationship strictly physical, but it's not long before they learn that they want something more.
Director: Ivan Reitman | Stars: Natalie Portman, Ashton Kutcher, Kevin Kline, Cary Elwes
Votes: 244,355 | Gross: $70.66M
55. Enter the Void (2009)
Not Rated | 161 min | Drama, Fantasy
An American drug dealer living in Tokyo is betrayed by his best friend and killed in a drug deal. His soul, observing the repercussions of his death, seeks resurrection.
Director: Gaspar Noé | Stars: Nathaniel Brown, Paz de la Huerta, Cyril Roy, Olly Alexander
Votes: 88,176 | Gross: $0.34M
56. Oldboy (2013)
R | 104 min | Action, Drama, Mystery
Obsessed with vengeance, a man sets out to find out why he was kidnapped and locked into solitary confinement for twenty years without reason.
Director: Spike Lee | Stars: Josh Brolin, Elizabeth Olsen, Samuel L. Jackson, Sharlto Copley
Votes: 80,910 | Gross: $2.19M
57. Wonderland (2003)
R | 104 min | Crime, Drama, Mystery
In the police investigation of a brutal crime scene, one man was at the center of it all: legendary porn star John Holmes.
Director: James Cox | Stars: Val Kilmer, Lisa Kudrow, Kate Bosworth, Christina Applegate
Votes: 23,386 | Gross: $1.06M
58. Fracture (2007)
R | 113 min | Crime, Drama, Thriller
After shooting his wife, Ted confesses his crime and asks the court to move his case to trial. He represents himself against Willy, a successful lawyer. But there's more to the case than meets the eye.
Director: Gregory Hoblit | Stars: Anthony Hopkins, Ryan Gosling, David Strathairn, Rosamund Pike
Votes: 219,225 | Gross: $39.02M
59. Insomnia (2002)
R | 118 min | Drama, Mystery, Thriller
Two Los Angeles homicide detectives are dispatched to a northern town where the sun doesn't set to investigate the methodical murder of a local teen.
Director: Christopher Nolan | Stars: Al Pacino, Robin Williams, Hilary Swank, Martin Donovan
Votes: 319,588 | Gross: $67.36M
60. Charade (1963)
Passed | 113 min | Comedy, Mystery, Romance
Romance and suspense ensue in Paris as a woman is pursued by several men who want a fortune her murdered husband had stolen. Whom can she trust?
Director: Stanley Donen | Stars: Cary Grant, Audrey Hepburn, Walter Matthau, James Coburn
Votes: 85,728 | Gross: $13.47M
61. Student Services (2010 TV Movie)
Not Rated | 100 min | Drama, Romance
Laura is a 19-year-old university freshman who desperately wants to do well in school. She works a part-time job but cannot make ends meet. One evening in which she is short of funds, she ... See full summary »
Director: Emmanuelle Bercot | Stars: Déborah François, Alain Cauchi, Mathieu Demy, Benjamin Siksou
Votes: 3,196
62. Phantom Thread (2017)
R | 130 min | Drama, Romance
Set in 1950s London, Reynolds Woodcock is a renowned dressmaker whose fastidious life is disrupted by a young, strong-willed woman, Alma, who becomes his muse and lover.
Director: Paul Thomas Anderson | Stars: Vicky Krieps, Daniel Day-Lewis, Lesley Manville, Julie Vollono
Votes: 145,788 | Gross: $21.02M
63. The First Wives Club (1996)
PG | 103 min | Comedy
Reunited by the death of a college friend, three divorced women seek revenge on the husbands who left them for younger women.
Director: Hugh Wilson | Stars: Goldie Hawn, Bette Midler, Diane Keaton, Maggie Smith
Votes: 54,321 | Gross: $105.49M
64. Random Harvest (1942)
Passed | 126 min | Drama, Romance
An amnesiac World War I veteran falls in love with a music hall star, only to suffer an accident which restores his original memories but erases his post-war life.
Director: Mervyn LeRoy | Stars: Ronald Colman, Greer Garson, Philip Dorn, Susan Peters
Votes: 8,436 | Gross: $10.14M
65. Wij (2018)
Unrated | 100 min | Drama
Eight teens - four guys and four girls - are the best of friends. One summer, out of boredom they experiment with all manner of new means to entertain themselves. This degenerates into some extreme behaviour and will lead to tragedy.
Director: Rene Eller | Stars: Aimé Claeys, Tijmen Govaerts, Pauline Casteleyn, Maxime Jacobs
Votes: 3,398
66. Definitely, Maybe (2008)
PG-13 | 112 min | Comedy, Drama, Romance
A political consultant tries to explain his impending divorce and past relationships to his 11-year-old daughter.
Director: Adam Brooks | Stars: Ryan Reynolds, Rachel Weisz, Abigail Breslin, An Nguyen
Votes: 173,418 | Gross: $31.97M
67. Hard Candy (2005)
R | 104 min | Drama, Thriller
Hayley's a smart, charming teenage girl. Jeff's a handsome, smooth fashion photographer. An Internet chat, a coffee shop meet-up, an impromptu fashion shoot back at Jeff's place. Jeff thinks it's his lucky night. He's in for a surprise.
Director: David Slade | Stars: Patrick Wilson, Elliot Page, Sandra Oh, Odessa Rae
Votes: 168,231 | Gross: $1.01M
68. Poison Ivy (1992)
R | 93 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: 20,180 | Gross: $1.83M
69. Stepmom (1998)
PG-13 | 125 min | Comedy, Drama
A terminally ill woman must deal with her ex-husband's new lover, who will be their children's stepmother.
Director: Chris Columbus | Stars: Julia Roberts, Susan Sarandon, Ed Harris, Jena Malone
Votes: 74,631 | Gross: $91.14M
70. The Wrong Missy (2020)
TV-MA | 90 min | Comedy, Romance
Tim thinks he's invited the woman of his dreams on a work retreat to Hawaii, realizing too late he mistakenly texted someone from a nightmare blind date.
Director: Tyler Spindel | Stars: David Spade, Lauren Lapkus, Nick Swardson, Geoff Pierson
Votes: 45,522
71. Any Given Sunday (1999)
R | 162 min | Drama, Sport
A behind-the-scenes look at the life-and-death struggles of modern-day gladiators and those who lead them.
Director: Oliver Stone | Stars: Al Pacino, Dennis Quaid, Cameron Diaz, James Woods
Votes: 125,993 | Gross: $75.53M
72. Machete (2010)
R | 105 min | Action, Crime, Thriller
After being set-up and betrayed by the man who hired him to assassinate a Texas Senator, an ex-Federale launches a brutal rampage of revenge against his former boss.
Directors: Ethan Maniquis, Robert Rodriguez | Stars: Danny Trejo, Michelle Rodriguez, Robert De Niro, Jessica Alba
Votes: 204,180 | Gross: $26.59M
73. The Other Woman (2014)
PG-13 | 109 min | Comedy, Romance
After discovering that her boyfriend is married, Carly meets the wife he's been betraying; when yet another affair is discovered, all three women team up to plot revenge on the three-timing S.O.B.
Director: Nick Cassavetes | Stars: Cameron Diaz, Leslie Mann, Kate Upton, Nikolaj Coster-Waldau
Votes: 150,234 | Gross: $83.91M
74. New York, I Love You (2008)
R | 103 min | Comedy, Drama, Romance
Eleven love stories set in one of the most loved and hated cities of the world, New York City.
Directors: Fatih Akin, Yvan Attal, Randall Balsmeyer, Allen Hughes, Shunji Iwai, Wen Jiang, Shekhar Kapur, Joshua Marston, Mira Nair, Natalie Portman, Brett Ratner | Stars: Shia LaBeouf, Natalie Portman, Bradley Cooper, Hayden Christensen
Votes: 47,895 | Gross: $1.59M
75. The Last Picture Show (1971)
R | 118 min | Drama, Romance
In 1951, a group of high schoolers come of age in a bleak, isolated, atrophied North Texas town that is slowly dying, both culturally and economically.
Director: Peter Bogdanovich | Stars: Timothy Bottoms, Jeff Bridges, Cybill Shepherd, Ben Johnson
Votes: 52,473 | Gross: $29.13M
76. Dirty Grandpa (2016)
R | 102 min | Comedy
Right before his wedding, an uptight guy is tricked into driving his grandfather, a lecherous former Army Lieutenant Colonel, to Florida for Spring Break.
Director: Dan Mazer | Stars: Robert De Niro, Zac Efron, Zoey Deutch, Aubrey Plaza
Votes: 133,480 | Gross: $35.59M
77. Babel (I) (2006)
R | 143 min | Drama
Tragedy strikes a married couple on vacation in the Moroccan desert, which jump starts an interlocking story involving four different families.
Director: Alejandro G. Iñárritu | Stars: Brad Pitt, Cate Blanchett, Gael García Bernal, Mohamed Akhzam
Votes: 317,382 | Gross: $34.30M
78. The Lover (1992)
R | 115 min | Biography, Drama, Romance
In 1929 French Indochina, a French teenage girl embarks on a reckless and forbidden romance with a wealthy, older Chinese man, each knowing that knowledge of their affair will bring drastic consequences to each other.
Director: Jean-Jacques Annaud | Stars: Jane March, Tony Ka Fai Leung, Jeanne Moreau, Frédérique Meininger
Votes: 23,534 | Gross: $4.90M
79. Blow-Up (1966)
Not Rated | 111 min | Drama, Mystery, Thriller
A fashion photographer unknowingly captures a death on film after following two lovers in a park.
Director: Michelangelo Antonioni | Stars: David Hemmings, Vanessa Redgrave, Sarah Miles, John Castle
Votes: 67,775
80. The Best Offer (2013)
R | 131 min | Crime, Drama, Mystery
Virgil Oldman, a wealthy art auctioneer, takes the help of a young artificer, Robert, to understand and woo Claire Ibbetson, a young heiress, who hires him to auction off an antique collection.
Director: Giuseppe Tornatore | Stars: Geoffrey Rush, Jim Sturgess, Sylvia Hoeks, Donald Sutherland
Votes: 128,776 | Gross: $0.09M
81. Bill & Ted's Excellent Adventure (1989)
PG | 90 min | Adventure, Comedy, Music
Two rock-'n-rolling teens, on the verge of failing their class, set out on a quest to make the ultimate school history report after being presented with a time machine.
Director: Stephen Herek | Stars: Keanu Reeves, Alex Winter, George Carlin, Terry Camilleri
Votes: 141,861 | Gross: $40.49M
82. Something's Gotta Give (2003)
PG-13 | 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: 129,354 | Gross: $124.73M
83. Lady Macbeth (2016)
R | 89 min | Drama, Romance
In 19th-century rural England, a young bride who has been sold into marriage discovers an unstoppable desire within herself as she enters into an affair with a worker on her estate.
Director: William Oldroyd | Stars: Florence Pugh, Cosmo Jarvis, Paul Hilton, Naomi Ackie
Votes: 27,349 | Gross: $1.13M
84. The Glass Castle (2017)
PG-13 | 127 min | Biography, Drama
A young girl comes of age in a dysfunctional family of nonconformist nomads with a mother who's an eccentric artist and an alcoholic father who would stir the children's imagination with hope as a distraction to their poverty.
Director: Destin Daniel Cretton | Stars: Brie Larson, Woody Harrelson, Naomi Watts, Ella Anderson
Votes: 38,617 | Gross: $17.27M
85. Sully (2016)
PG-13 | 96 min | Biography, Drama
When pilot Chesley "Sully" Sullenberger lands his damaged plane on the Hudson River in order to save the flight's passengers and crew, some consider him a hero while others think he was reckless.
Director: Clint Eastwood | Stars: Tom Hanks, Aaron Eckhart, Laura Linney, Valerie Mahaffey
Votes: 298,616 | Gross: $125.07M
86. Living (2022)
PG-13 | 102 min | Drama
In 1950s London, a humorless bureaucrat decides to take time off work to experience life after receiving a grim diagnosis.
Director: Oliver Hermanus | Stars: Bill Nighy, Aimee Lou Wood, Alex Sharp, Adrian Rawlins
Votes: 32,900
87. Big Love (2006–2011)
TV-MA | 60 min | Drama
A Utah polygamist who owns home improvement stores in the Salt Lake City area juggles relationships with three wives while trying to keep his complex family life from becoming a public scandal.
Stars: Bill Paxton, Jeanne Tripplehorn, Chloë Sevigny, Ginnifer Goodwin
Votes: 23,303
88. The Girl with the Dragon Tattoo (2009)
R | 152 min | Crime, Drama, Mystery
A journalist is aided by a young female hacker in his search for the killer of a woman who has been dead for forty years.
Director: Niels Arden Oplev | Stars: Michael Nyqvist, Noomi Rapace, Ewa Fröling, Lena Endre
Votes: 223,465 | Gross: $10.10M
89. The Lodge (2019)
R | 108 min | Drama, Horror, Mystery
A soon-to-be stepmom is snowed in with her fiancé's two children at a remote holiday village. Just as relations begin to thaw between the trio, some strange and frightening events take place.
Directors: Severin Fiala, Veronika Franz | Stars: Riley Keough, Jaeden Martell, Lia McHugh, Richard Armitage
Votes: 57,995
90. Mystic Pizza (1988)
R | 104 min | Comedy, Drama, Romance
Three teenage girls come of age while working at a pizza parlor in the Connecticut town of Mystic.
Director: Donald Petrie | Stars: Annabeth Gish, Julia Roberts, Lili Taylor, Vincent D'Onofrio
Votes: 32,543 | Gross: $12.79M
91. Audition (1999)
R | 115 min | Drama, Horror, Mystery
A widower takes an offer to screen girls at a special audition, arranged for him by a friend to find him a new wife. The one he fancies is not who she appears to be after all.
Director: Takashi Miike | Stars: Ryo Ishibashi, Eihi Shiina, Tetsu Sawaki, Jun Kunimura
Votes: 89,388
92. The 'Burbs (1989)
PG | 102 min | Comedy, Mystery, Thriller
An overstressed suburbanite and his neighbors are convinced that the new family on the block is part of a murderous Satanic cult.
Director: Joe Dante | Stars: Tom Hanks, Bruce Dern, Carrie Fisher, Corey Feldman
Votes: 83,669 | Gross: $36.60M
93. The Assassination of Jesse James by the Coward Robert Ford (2007)
R | 160 min | Biography, Crime, Drama
Robert Ford, who has idolized Jesse James since childhood, tries hard to join the resurgent gang of the Missouri outlaw, but gradually becomes resentful of the bandit leader.
Director: Andrew Dominik | Stars: Brad Pitt, Casey Affleck, Sam Shepard, Mary-Louise Parker
Votes: 192,996 | Gross: $3.90M
94. Best in Show (2000)
PG-13 | 90 min | Comedy
A behind-the-scenes look into the highly competitive and cut-throat world of dog shows through the eyes of a group of ruthless dog owners.
Director: Christopher Guest | Stars: Fred Willard, Eugene Levy, Catherine O'Hara, Jennifer Coolidge
Votes: 67,026 | Gross: $18.72M
95. The Remains of the Day (1993)
PG | 134 min | Drama, Romance
A butler who sacrificed body and soul to service in the years leading up to World War II realizes too late how misguided his loyalty was to his lordly employer.
Director: James Ivory | Stars: Anthony Hopkins, Emma Thompson, John Haycraft, Christopher Reeve
Votes: 84,629 | Gross: $22.95M
96. Chloe (2009)
R | 96 min | Drama, Mystery, Thriller
Suspecting her husband of infidelity, gynecologist Dr. Catherine Stewart hires an escort named Chloe in order to test his faithfulness. Soon, the relationships between all three intensify.
Director: Atom Egoyan | Stars: Julianne Moore, Amanda Seyfried, Liam Neeson, Max Thieriot
Votes: 77,970 | Gross: $3.07M
97. Witness for the Prosecution (1957)
Approved | 116 min | Crime, Drama, Mystery
A veteran British barrister must defend his client in a murder trial that has surprise after surprise.
Director: Billy Wilder | Stars: Tyrone Power, Marlene Dietrich, Charles Laughton, Elsa Lanchester
Votes: 138,160 | Gross: $8.18M
98. 10 (1979)
R | 122 min | Comedy, Romance
A Hollywood composer goes through a mid-life crisis and becomes infatuated with a sexy, newly married woman.
Director: Blake Edwards | Stars: Dudley Moore, Bo Derek, Julie Andrews, Robert Webber
Votes: 19,298 | Gross: $74.87M
99. Far from the Madding Crowd (2015)
PG-13 | 119 min | Drama, Romance
In Victorian England, the independent and headstrong Bathsheba Everdene attracts three very different suitors: Gabriel Oak, a sheep farmer; Frank Troy, a reckless Sergeant; and William Boldwood, a prosperous and mature bachelor.
Director: Thomas Vinterberg | Stars: Carey Mulligan, Matthias Schoenaerts, Michael Sheen, Tom Sturridge
Votes: 53,803 | Gross: $12.23M
100. Dark Shadows (2012)
PG-13 | 113 min | Comedy, Fantasy, Horror
An imprisoned vampire, Barnabas Collins, is set free and returns to his ancestral home, where his dysfunctional descendants are in need of his protection.
Director: Tim Burton | Stars: Johnny Depp, Michelle Pfeiffer, Eva Green, Helena Bonham Carter
Votes: 280,740 | Gross: $79.73M