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. 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: 292,898 | Gross: $39.67M
4. 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: 950,952 | Gross: $19.50M
5. 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: 384,296 | Gross: $107.83M
6. The Big Lebowski (1998)
R | 117 min | Comedy, Crime
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: 676,832 | Gross: $17.50M
7. 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: 720,793 | Gross: $74.10M
8. Fracture (2007)
R | 113 min | Crime, Drama
An attorney intent on climbing the career ladder toward success, finds an unlikely opponent in a manipulative criminal he is trying to prosecute.
Votes: 172,663 | Gross: $39.02M
R | 115 min | Crime, Drama
A mother personally challenges the local authorities to solve her daughter's murder when they fail to catch the culprit.
Votes: 364,378 | Gross: $54.51M
11. 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: 470,382 | Gross: $0.71M
12. 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: 78,303 | Gross: $4.06M
13. 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: 394,100 | Gross: $102.52M
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: 841,592 | Gross: $34.40M
15. 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: 408,758 | Gross: $36.76M
16. 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: 111,081 | Gross: $51.27M
17. 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: 196,645 | Gross: $53.86M
18. 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: 90,566 | Gross: $21.02M
19. 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: 233,958 | Gross: $79.73M
20. 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: 205,882 | Gross: $103.03M
22. 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: 232,093 | Gross: $50.93M
23. 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: 549,197 | Gross: $127.51M
24. 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: 258,686 | Gross: $148.48M
25. 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: 238,012 | Gross: $32.53M
26. 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: 268,882 | Gross: $198.68M
27. 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: 94,623 | Gross: $8.83M
28. 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: 329,313 | Gross: $3.20M
30. Season of the Witch (1982)
R | 98 min | Horror, Mystery, Sci-Fi
Kids all over America want Silver Shamrock masks for Halloween. Doctor Daniel Challis seeks to uncover a plot by Silver Shamrock owner Conal Cochran.
Votes: 39,566 | Gross: $14.40M
31. 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: 94,105 | Gross: $43.18M
34. 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: 200,712 | Gross: $70.66M
35. 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: 108,015 | Gross: $6.22M
36. 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: 257,383 | Gross: $67.36M
38. Home Again (2017)
PG-13 | 97 min | Comedy, Drama, Romance
Life for a single mom in Los Angeles takes an unexpected turn when she allows three young guys to move in with her.
Votes: 24,132 | Gross: $27.02M
39. 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: 25,209 | Gross: $17.27M
40. 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: 304,266 | Gross: $83.82M
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: 159,211 | Gross: $3.90M
42. 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: 104,385 | Gross: $35.54M
43. Rumor Has It... (2005)
PG-13 | 97 min | Comedy, Drama, Romance
Sarah Huttinger is a woman who learns that her family was the inspiration for the book and film "The Graduate" -- and that she just might be the offspring of the well-documented event.
Votes: 49,744 | Gross: $43.00M
44. It's Complicated (2009)
R | 120 min | Comedy, Drama, Romance
When attending their son's college graduation, a couple reignite the spark in their relationship. But the complicated fact is they're divorced and he's remarried.
Votes: 81,998 | Gross: $112.74M
45. 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: 80,825 | Gross: $0.33M
46. Enter the Void (2009)
Not Rated | 161 min | Drama, Fantasy
A French 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.
Votes: 63,137 | Gross: $0.34M
47. Café Society (2016)
PG-13 | 96 min | Comedy, Drama, Romance
In the 1930s, a Bronx native moves to Hollywood and falls in love with a young woman who is seeing a married man.
Votes: 64,397 | Gross: $11.10M
49. Assassination Nation (2018)
R | 108 min | Action, Comedy, Crime
After a malicious data hack exposes the secrets of the perpetually American town of Salem, chaos descents and four girls must fight to survive, while coping with the hack themselves.
Votes: 11,136 | Gross: $1.96M