Most Popular "Older Man Younger Woman Relationship" Titles
- Movies or TV
- IMDb Rating
- Instant Watch Options
- In Theaters
- On TV
- Release Year
2. The Big Lebowski (1998)
R | 117 min | Comedy, Crime, Mystery
"The Dude" Lebowski, mistaken for a millionaire Lebowski, seeks restitution for his ruined rug and enlists his bowling buddies to help get it.
Votes: 570,354 | Gross: $17.44M
3. Léon: The Professional (1994)
R | 110 min | Crime, Drama, Thriller
Mathilda, a 12-year-old girl, is reluctantly taken in by Léon, a professional assassin, after her family is murdered. Léon and Mathilda form an unusual relationship, as she becomes his protégée and learns the assassin's trade.
Votes: 772,623 | Gross: $32.35M
5. 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: 71,973 | Gross: $35.54M
6. Eternal Sunshine of the Spotless Mind (2004)
R | 108 min | Drama, Romance, Sci-Fi
When their relationship turns sour, a couple undergoes a procedure to have each other erased from their memories. But it is only through the process of loss that they discover what they had to begin with.
Votes: 708,550 | Gross: $34.13M
7. 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: 345,236 | Gross: $102.52M
8. Oldeuboi (2003)
R | 120 min | Drama, Mystery, Thriller
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: 380,995 | Gross: $2.18M
10. 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: 42,856 | Gross: $11.08M
11. 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: 681,972 | Gross: $74.10M
12. Gone with the Wind (1939)
G | 238 min | Drama, History, Romance
American film classic in which a manipulative woman and a roguish man conduct a turbulent romance during the American Civil War and Reconstruction periods.
Votes: 226,921 | Gross: $198.66M
13. 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: 480,870 | Gross: $127.49M
15. As Good as It Gets (1997)
PG-13 | 139 min | Comedy, Drama, Romance
A single mother/waitress, a misanthropic author, and a gay artist form an unlikely friendship after the artist is assaulted in a robbery.
Votes: 232,274 | Gross: $147.64M
16. 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: 201,107 | Gross: $50.92M
17. Fracture (2007)
R | 113 min | Crime, Drama, Mystery
An attorney, intent on climbing the career ladder toward success, finds an unlikely opponent in a manipulative criminal he is trying to prosecute.
Votes: 147,079 | Gross: $39.00M
20. 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: 163,985 | Gross: $53.85M
21. Nymphomaniac: Vol. II (2013)
Not Rated | 123 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: 64,670 | Gross: $0.33M
22. 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: 180,409 | Gross: $103.03M
23. 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: 207,767 | Gross: $79.71M
24. 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: 214,779 | Gross: $32.52M
25. Secretary (2002)
R | 104 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: 70,514 | Gross: $4.05M
27. 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: 176,733 | Gross: $70.63M
30. The Girl with the Dragon Tattoo (2009)
R | 152 min | Crime, Drama, Mystery
A journalist is aided in his search for a woman who has been missing -- or dead -- for forty years by a young female hacker.
Votes: 180,853 | Gross: $10.10M
31. The Best Offer (2013)
R | 131 min | Crime, Drama, Mystery
In the world of high-end art auctions and antiques, Virgil Oldman is an elderly and esteemed but eccentric genius art-expert, known and appreciated by the world. Oldman is hired by a ... See full summary »
Votes: 76,491 | Gross: $0.09M
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: 142,250 | Gross: $3.90M
33. Vertigo (1958)
PG | 128 min | Mystery, Romance, Thriller
A San Francisco detective suffering from acrophobia investigates the strange activities of an old friend's wife, all the while becoming dangerously obsessed with her.
Votes: 265,410 | Gross: $3.20M
35. 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: 81,614 | Gross: $42.70M
36. Up in the Air (I) (2009)
R | 109 min | Drama, Romance
Ryan Bingham enjoys living out of a suitcase for his job traveling around the country firing people, but finds that lifestyle threatened by the presence of a potential love interest and a new hire.
Votes: 278,220 | Gross: $83.81M
37. 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.
Votes: 132,254 | Gross: $31.97M
38. Jackie Brown (1997)
R | 154 min | Crime, 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: 250,255 | Gross: $39.65M
39. Mildred Pierce (1945)
Not Rated | 111 min | Crime, Drama, Film-Noir
A hard-working mother inches towards disaster as she divorces her husband and starts a successful restaurant business to support her spoiled daughter.
42. We Are Your Friends (2015)
R | 96 min | Drama, Music, Romance
Caught between a forbidden romance and the expectations of his friends, aspiring DJ Cole Carter attempts to find the path in life that leads to fame and fortune.
Votes: 25,077 | Gross: $3.59M
46. 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: 227,646 | Gross: $67.26M
48. 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: 251,704 | Gross: $34.30M
49. 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: 99,324 | Gross: $6.20M