Most Popular Older Man Younger Woman Relationship Movies and TV Shows
- Movies or TV
- IMDb Rating
- Instant Watch Options
- In Theaters
- On TV
- Release Year
2. 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: 958,287 | Gross: $19.50M
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: 370,174 | Gross: $54.51M
4. 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: 388,706 | Gross: $107.83M
6. 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: 722,336 | Gross: $74.10M
7. 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: 78,751 | Gross: $4.06M
8. 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: 680,937 | Gross: $17.50M
9. 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: 396,175 | Gross: $102.52M
10. 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: 473,953 | Gross: $0.71M
11. 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: 233,267 | Gross: $50.93M
12. 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: 846,387 | Gross: $34.40M
14. The Curious Case of Benjamin Button (2008)
PG-13 | 166 min | Drama, Fantasy, Romance
Tells the story of Benjamin Button, a man who starts aging backwards with bizarre consequences.
Votes: 552,100 | Gross: $127.51M
15. 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: 111,550 | Gross: $51.27M
17. 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: 105,260 | Gross: $35.59M
18. 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: 270,282 | Gross: $198.68M
19. 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: 92,294 | Gross: $21.02M
20. 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: 294,962 | Gross: $39.67M
21. 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: 95,124 | Gross: $8.83M
23. 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: 238,892 | Gross: $32.53M
24. 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: 206,951 | Gross: $103.03M
25. 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: 173,991 | Gross: $39.02M
26. Guess Who's Coming to Dinner (1967)
Not Rated | 108 min | Comedy, Drama
A couple's attitudes are challenged when their daughter introduces them to her African-American fiancé.
Votes: 36,056 | Gross: $56.70M
27. 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: 198,102 | Gross: $53.86M
29. 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: 331,902 | Gross: $3.20M
30. The 'Burbs (1989)
PG | 102 min | Comedy, Mystery, Thriller
An overstressed suburbanite and his fellow neighbors are convinced that the new family on the block are part of a murderous Satanic cult.
Votes: 63,677 | Gross: $36.60M
31. 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: 411,598 | Gross: $36.76M
32. 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: 94,684 | Gross: $43.18M
34. 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: 259,854 | Gross: $148.48M
35. 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: 201,598 | Gross: $70.66M
37. Doctor Zhivago (1965)
PG-13 | 197 min | Drama, Romance, War
The life of a Russian physician and poet who, although married to another, falls in love with a political activist's wife and experiences hardship during World War I and then the October Revolution.
Votes: 65,756 | Gross: $111.72M
38. Ghost World (2001)
R | 111 min | Comedy, Drama
With only the plan of moving in together after high school, two unusually devious friends seek direction in life. As a mere gag, they respond to a man's newspaper ad for a date, only to find it will greatly complicate their lives.
Votes: 108,406 | Gross: $6.22M
39. 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: 258,674 | Gross: $67.36M
40. 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.
Votes: 235,305 | Gross: $79.73M
41. A Face in the Crowd (1957)
Not Rated | 126 min | Drama, Music
An Arkansas drifter becomes an overnight media sensation. As he becomes drunk with fame and power, will he ever be exposed as the fraud he has become?
42. 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: 81,457 | Gross: $0.33M
43. 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: 200,932 | Gross: $10.10M
44. Last Tango in Paris (1972)
NC-17 | 129 min | Drama, Romance
A young Parisian woman meets a middle-aged American businessman who demands their clandestine relationship be based only on sex.
Votes: 46,267 | Gross: $36.14M
45. 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 West Texas town that is slowly dying, both culturally and economically.
Votes: 38,873 | Gross: $29.13M
47. Colette (I) (2018)
R | 111 min | Biography, Drama, History
Colette is pushed by her husband to write novels under his name. Upon their success, she fights to make her talents known, challenging gender norms.
Votes: 15,187 | Gross: $5.14M
50. 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: 305,239 | Gross: $83.82M