Most Popular Older Man Younger Woman Relationship Movies and TV Shows
- Movies or TV
- IMDb Rating
- Instant Watch Options
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1. Once Upon a Time... in Hollywood (2019)
R | 161 min | Comedy, Drama
A faded television actor and his stunt double strive to achieve fame and success in the film industry during the final years of Hollywood's Golden Age in 1969 Los Angeles.
Votes: 338,674 | Gross: $135.37M
3. Baby Driver (2017)
R | 113 min | Action, Crime, Drama
After being coerced into working for a crime boss, a young getaway driver finds himself taking part in a heist doomed to fail.
Votes: 393,785 | Gross: $107.83M
5. Léon: The Professional (1994)
R | 110 min | Action, Crime, Drama
Mathilda, a 12-year-old girl, is reluctantly taken in by Léon, a professional assassin, after her family is murdered. An unusual relationship forms as she becomes his protégée and learns the assassin's trade.
Votes: 966,020 | Gross: $19.50M
6. The Girl with the Dragon Tattoo (2011)
R | 158 min | Crime, Drama, Mystery
Journalist Mikael Blomkvist is aided in his search for a woman who has been missing for forty years by Lisbeth Salander, a young computer hacker.
Votes: 398,573 | Gross: $102.52M
R | 115 min | Comedy, Crime, Drama
A mother personally challenges the local authorities to solve her daughter's murder when they fail to catch the culprit.
Votes: 377,066 | Gross: $54.51M
8. Almost Famous (2000)
R | 122 min | Adventure, Comedy, Drama
A high-school boy is given the chance to write a story for Rolling Stone Magazine about an up-and-coming rock band as he accompanies them on their concert tour.
Votes: 240,289 | Gross: $32.53M
9. The Big Lebowski (1998)
R | 117 min | Comedy, Crime, Sport
Jeff "The Dude" Lebowski, mistaken for a millionaire of the same name, seeks restitution for his ruined rug and enlists his bowling buddies to help get it.
Votes: 685,643 | Gross: $17.50M
12. Atonement (2007)
R | 123 min | Drama, Mystery, Romance
Fledgling writer Briony Tallis, as a thirteen-year-old, irrevocably changes the course of several lives when she accuses her older sister's lover of a crime he did not commit.
Votes: 234,678 | Gross: $50.93M
13. Oldboy (2003)
R | 120 min | Action, Drama, Mystery
After being kidnapped and imprisoned for fifteen years, Oh Dae-Su is released, only to find that he must find his captor in five days.
Votes: 477,856 | Gross: $0.71M
14. Eternal Sunshine of the Spotless Mind (2004)
R | 108 min | Drama, Romance, Sci-Fi
When their relationship turns sour, a couple undergoes a medical procedure to have each other erased from their memories.
Votes: 852,541 | Gross: $34.40M
15. 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.
Votes: 94,766 | Gross: $21.02M
16. Sin City (2005)
R | 124 min | Crime, Thriller
A film that explores the dark and miserable town, Basin City, and tells the story of three different people, all caught up in violent corruption.
Votes: 724,196 | Gross: $74.10M
17. Just Go with It (2011)
PG-13 | 117 min | Comedy, Romance
On a weekend trip to Hawaii, a plastic surgeon convinces his loyal assistant to pose as his soon-to-be-divorced wife in order to cover up a careless lie he told to his much-younger girlfriend.
Votes: 208,287 | Gross: $103.03M
19. A Cure for Wellness (2016)
R | 146 min | Drama, Fantasy, Horror
An ambitious young executive is sent to retrieve his company's CEO from an idyllic but mysterious "wellness center" at a remote location in the Swiss Alps, but soon suspects that the spa's treatments are not what they seem.
Votes: 75,538 | Gross: $8.11M
20. Gone with the Wind (1939)
Passed | 238 min | Drama, History, Romance
A manipulative woman and a roguish man conduct a turbulent romance during the American Civil War and Reconstruction periods.
Votes: 272,188 | Gross: $198.68M
21. Jackie Brown (1997)
R | 154 min | Crime, Drama, Thriller
A middle-aged woman finds herself in the middle of a huge conflict that will either make her a profit or cost her life.
Votes: 297,391 | Gross: $39.67M
23. 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.
Votes: 202,677 | Gross: $70.66M
24. 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.
Votes: 16,512 | Gross: $1.13M
25. Up in the Air (I) (2009)
R | 109 min | Comedy, Drama, Romance
Ryan Bingham enjoys living out of a suitcase for his job, travelling around the country firing people, but finds that lifestyle threatened by the presence of a potential love interest, and a new hire.
Votes: 306,595 | Gross: $83.82M
26. Mulholland Drive (2001)
R | 147 min | Drama, Mystery, Thriller
After a car wreck on the winding Mulholland Drive renders a woman amnesiac, she and a perky Hollywood-hopeful search for clues and answers across Los Angeles in a twisting venture beyond dreams and reality.
Votes: 299,573 | Gross: $7.22M
27. Secretary (2002)
R | 107 min | Comedy, Drama, Romance
A young woman, recently released from a mental hospital, gets a job as a secretary to a demanding lawyer, where their employer-employee relationship turns into a sexual, sadomasochistic one.
Votes: 79,227 | Gross: $4.06M
28. 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.
Votes: 106,192 | Gross: $35.59M
29. 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.
Votes: 261,228 | Gross: $148.48M
30. 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 titular opposites.
Votes: 95,457 | Gross: $43.18M
31. Fracture (2007)
R | 113 min | Crime, Drama, Thriller
An attorney intent on climbing the career ladder toward success, finds an unlikely opponent in a manipulative criminal he is trying to prosecute.
Votes: 175,473 | Gross: $39.02M
33. Movie 43 (2013)
R | 94 min | Comedy
A series of interconnected short films follows a washed-up producer as he pitches insane story lines featuring some of the biggest stars in Hollywood.
Directors: Elizabeth Banks, Steven Brill, Steve Carr, Rusty Cundieff, James Duffy, Griffin Dunne, Peter Farrelly, Patrik Forsberg, Will Graham, James Gunn, Brett Ratner, Jonathan van Tulleken, Bob Odenkirk | Stars: Emma Stone, Stephen Merchant, Richard Gere, Liev Schreiber
Votes: 95,578 | Gross: $8.83M
34. First Reformed (2017)
R | 113 min | Drama, Mystery, Thriller
A minister of a small congregation in upstate New York grapples with mounting despair brought on by tragedy, worldly concerns and a tormented past.
Votes: 39,381 | Gross: $3.45M
35. The Phantom of the Opera (2004)
PG-13 | 143 min | Drama, Musical, Romance
A young soprano becomes the obsession of a disfigured and murderous musical genius who lives beneath the Paris Opéra House.
Votes: 111,979 | Gross: $51.27M
36. Vertigo (1958)
PG | 128 min | Mystery, Romance, Thriller
A former police detective juggles wrestling with his personal demons and becoming obsessed with a hauntingly beautiful woman.
Votes: 334,693 | Gross: $3.20M
38. 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.
Votes: 199,760 | Gross: $53.86M
39. Beach Party (1963)
Not Rated | 101 min | Comedy, Musical, Romance
The first of the five official American-International "Beach Party" movies. Anthropology Professor Robert Orwell Sutwell and his secretary Marianne are studying the sex habits of teenagers.... See full summary »
40. Rear Window (1954)
PG | 112 min | Mystery, Thriller
A wheelchair-bound photographer spies on his neighbors from his apartment window and becomes convinced one of them has committed murder.
Votes: 414,367 | Gross: $36.76M
41. 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.
Votes: 201,786 | Gross: $10.10M
43. 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.
Votes: 260,086 | Gross: $67.36M
44. Bill & Ted's Excellent Adventure (1989)
PG | 90 min | Adventure, Comedy, Music
Two seemingly dumb teens set off on a quest to prepare the ultimate historical presentation with the help of a time machine.
Votes: 103,891 | Gross: $40.49M
45. Babel (I) (2006)
R | 143 min | Drama
Tragedy strikes a married couple on vacation in the Moroccan desert, touching off an interlocking story involving four different families.
Votes: 278,442 | Gross: $34.30M
46. 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.
Votes: 26,113 | Gross: $17.27M
R | 160 min | Biography, Crime, Drama
Robert Ford, who's idolized Jesse James since childhood, tries hard to join the reforming gang of the Missouri outlaw, but gradually becomes resentful of the bandit leader.
Votes: 160,825 | Gross: $3.90M
50. Nymphomaniac: Vol. II (2013)
Not Rated | 124 min | Drama
The continuation of Joe's sexually dictated life delves into the darker aspects of her adulthood, obsessions and what led to her being in Seligman's care.
Votes: 82,141 | Gross: $0.33M