Sort by Popularity - Most Popular Movies and TV Shows tagged with keyword "older-man-younger-woman-relationship"
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51. 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: 150,480 | Gross: $83.91M
52. As Good as It Gets (1997)
PG-13 | 139 min | Comedy, Drama, Romance
A single mother and waitress, a misanthropic author, and a gay artist form an unlikely friendship after the artist is assaulted in a robbery.
Director: James L. Brooks | Stars: Jack Nicholson, Helen Hunt, Greg Kinnear, Cuba Gooding Jr.
Votes: 319,503 | Gross: $148.48M
53. The Hot Spot (1990)
R | 130 min | Crime, Drama, Romance
Upon arriving to a small town, a drifter quickly gets into trouble with the local authorities - and the local women - after he robs a bank.
Director: Dennis Hopper | Stars: Don Johnson, Virginia Madsen, Jennifer Connelly, Charles Martin Smith
Votes: 13,602 | Gross: $1.29M
54. Focus (II) (2015)
R | 105 min | Comedy, Crime, Drama
In the midst of veteran con man Nicky's latest scheme, a woman from his past - now an accomplished femme fatale - shows up and throws his plans for a loop.
Directors: Glenn Ficarra, John Requa | Stars: Will Smith, Margot Robbie, Rodrigo Santoro, Adrian Martinez
Votes: 275,719 | Gross: $53.86M
55. 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: 219,680 | Gross: $39.02M
56. 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: 204,356 | Gross: $26.59M
57. 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: 45,717
58. 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: 146,166 | Gross: $21.02M
59. Deep Impact (1998)
PG-13 | 120 min | Action, Drama, Sci-Fi
A comet is discovered to be on a collision course with Earth. As doomsday nears, the human race prepares for the worst.
Director: Mimi Leder | Stars: Robert Duvall, Téa Leoni, Elijah Wood, Morgan Freeman
Votes: 191,056 | Gross: $140.46M
60. 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: 140,894
61. 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: 88,362 | Gross: $0.34M
62. 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: 142,166 | Gross: $40.49M
63. 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: 129,581 | Gross: $124.73M
64. The Edge (1997)
R | 117 min | Action, Adventure, Drama
An intellectual billionaire and two other men struggle to band together and survive after getting stranded in the Alaskan wilderness with a blood-thirsty Kodiak Bear hunting them down.
Director: Lee Tamahori | Stars: Anthony Hopkins, Alec Baldwin, Elle Macpherson, Harold Perrineau
Votes: 79,629 | Gross: $27.78M
65. Rio Bravo (1959)
Passed | 141 min | Western
A small-town sheriff in the American West enlists the help of a disabled man, a drunk, and a young gunfighter in his efforts to hold in jail the brother of the local bad guy.
Director: Howard Hawks | Stars: John Wayne, Dean Martin, Ricky Nelson, Angie Dickinson
Votes: 68,373 | Gross: $12.54M
66. 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: 281,110 | Gross: $79.73M
67. Up in the Air (I) (2009)
R | 109 min | Comedy, Drama, Romance
Ryan's job is to travel around the country firing off people. When his boss hires Natalie, who proposes firing people via video conference, he tries to convince her that her method is a mistake.
Director: Jason Reitman | Stars: George Clooney, Vera Farmiga, Anna Kendrick, Jason Bateman
Votes: 350,031 | Gross: $83.82M
68. 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: 53,904 | Gross: $12.23M
69. Shampoo (1975)
R | 110 min | Comedy, Drama
On Election Day, 1968, a hairdresser and ladies' man is too busy cutting hair and dealing with his various girlfriends and his mistress, whose husband he meets and finds out is having an affair with his ex-girlfriend.
Director: Hal Ashby | Stars: Warren Beatty, Julie Christie, Goldie Hawn, Lee Grant
Votes: 14,281 | Gross: $49.41M
70. Dirty Grandpa (2016)
R | 102 min | Comedy
Right before his wedding, an uptight corporate lawyer 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: 133,782 | Gross: $35.59M
71. 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: 317,666 | Gross: $34.30M
72. 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: 85,956 | Gross: $13.47M
73. 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: 3,414
74. 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: 223,639 | Gross: $10.10M
75. The Bridges of Madison County (1995)
PG-13 | 135 min | Drama, Romance
Photographer Robert Kincaid wanders into the life of housewife Francesca Johnson for four days in the 1960s.
Director: Clint Eastwood | Stars: Clint Eastwood, Meryl Streep, Annie Corley, Victor Slezak
Votes: 89,358 | Gross: $71.52M
76. 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: 193,265 | Gross: $3.90M
77. 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: 58,177
78. Notes on a Scandal (2006)
R | 92 min | Crime, Drama, Romance
A veteran high school teacher befriends a younger art teacher, who is having an affair with one of her fifteen-year-old students. However, her intentions with this new "friend" also go well beyond a platonic friendship.
Director: Richard Eyre | Stars: Cate Blanchett, Judi Dench, Andrew Simpson, Tom Georgeson
Votes: 84,838 | Gross: $17.51M
79. 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: 168,432 | Gross: $1.01M
80. 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: 67,928
81. 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: 5,953
82. 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: 23,582 | Gross: $4.90M
83. 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: 89,658
84. The Parent Trap (1961)
Passed | 129 min | Comedy, Family, Romance
Teenage twin sisters swap places and scheme to reunite their divorced parents.
Director: David Swift | Stars: Hayley Mills, Maureen O'Hara, Brian Keith, Charles Ruggles
Votes: 24,091
85. 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: 129,040 | Gross: $0.09M
86. 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: 32,653 | Gross: $12.79M
87. The Pledge (I) (2001)
R | 124 min | Crime, Drama, Mystery
A retiring police detective pledges to catch the killer of a young child.
Director: Sean Penn | Stars: Jack Nicholson, Benicio Del Toro, Patricia Clarkson, Beau Daniels
Votes: 68,082 | Gross: $19.72M
88. 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: 74,769 | Gross: $91.14M
89. 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: 83,881 | Gross: $36.60M
90. Baby Doll (1956)
Approved | 114 min | Comedy, Drama
An immature, naive teenage bride holds her anxious husband at bay while flirting with an amorous Sicilian farmer.
Director: Elia Kazan | Stars: Karl Malden, Carroll Baker, Eli Wallach, Mildred Dunnock
Votes: 8,320
91. Bitter Moon (1992)
R | 139 min | Drama, Romance, Thriller
After hearing stories of her, a passenger on a cruise ship develops an irresistible infatuation with an eccentric paraplegic's wife.
Director: Roman Polanski | Stars: Hugh Grant, Kristin Scott Thomas, Emmanuelle Seigner, Peter Coyote
Votes: 42,886 | Gross: $1.86M
92. 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: 23,344
93. 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: 27,455 | Gross: $1.13M
94. La Belle Noiseuse (1991)
Unrated | 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: 9,435 | Gross: $0.41M
95. Beautiful Girls (1996)
R | 112 min | Comedy, Drama, Romance
A piano player at a crossroads in his life returns home to his friends and their own problems with life and love.
Director: Ted Demme | Stars: Matt Dillon, Timothy Hutton, Noah Emmerich, Annabeth Gish
Votes: 34,874 | Gross: $10.60M
96. Crashing (2016)
TV-MA | 30 min | Comedy
A comedy series following the lives of six 20- and 30-somethings living together as property guardians of a large, disused hospital.
Stars: Phoebe Waller-Bridge, Jonathan Bailey, Julie Dray, Louise Ford
Votes: 26,348
97. 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: 78,131 | Gross: $3.07M
98. 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: 67,169 | Gross: $18.72M
99. 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: 33,184
100. In the Line of Fire (1993)
R | 128 min | Action, Crime, Drama
Secret Service agent Frank Horrigan couldn't save Kennedy, but he's determined not to let a clever assassin take out this president.
Director: Wolfgang Petersen | Stars: Clint Eastwood, John Malkovich, Rene Russo, Dylan McDermott
Votes: 114,198 | Gross: $102.31M