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: 569,811 | Gross: $17.44M
4. 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: 771,884 | Gross: $32.35M
5. 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: 344,924 | Gross: $102.52M
6. 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: 71,673 | Gross: $35.54M
7. 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: 707,929 | Gross: $34.13M
9. 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: 380,566 | Gross: $2.18M
11. 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: 163,787 | Gross: $53.85M
12. 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: 681,757 | Gross: $74.10M
13. 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: 226,744 | Gross: $198.66M
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: 480,514 | Gross: $127.49M
15. 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: 200,957 | Gross: $50.92M
18. 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: 146,942 | Gross: $39.00M
19. Swimming Pool (2003)
R | 102 min | Crime, Drama, Mystery
A British mystery author visits her publisher's home in the South of France, where her interaction with his unusual daughter sets off some touchy dynamics.
Votes: 36,055 | Gross: $10.11M
21. 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: 70,483 | Gross: $4.05M
22. 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: 232,117 | Gross: $147.64M
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: 142,142 | Gross: $3.90M
25. 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: 176,605 | Gross: $70.63M
26. 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: 214,660 | Gross: $32.52M
27. 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: 207,649 | Gross: $79.71M
28. 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: 180,751 | Gross: $10.10M
29. 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: 64,590 | Gross: $0.33M
30. 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: 76,354 | Gross: $0.09M
31. 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: 180,300 | Gross: $103.03M
32. The Last Sunset (1961)
Approved | 112 min | Drama, Romance, Western
Brendan O'Malley arrives at the Mexican home of old flame Belle Breckenridge to find her married to a drunkard getting ready for a cattle drive to Texas. Hot on O'Malley's heels is lawman ... See full summary »
33. The 'Burbs (1989)
PG | 101 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 cult.
Votes: 53,857 | Gross: $36.60M
34. 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: 99,276 | Gross: $6.20M
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: 278,106 | Gross: $83.81M
37. 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: 265,151 | Gross: $3.20M
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: 250,071 | Gross: $39.65M
39. The Other Woman (2014)
PG-13 | 109 min | Comedy, Romance
After discovering her boyfriend is married, Carly soon meets the wife he's been betraying. And when yet another love affair is discovered, all three women team up to plot revenge on the three-timing S.O.B.
Votes: 109,617 | Gross: $83.91M
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: 227,501 | Gross: $67.26M
44. 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: 25,030 | Gross: $3.59M
46. I Saw the Light (2015)
R | 123 min | Biography, Drama, Music
The story of the country-western singer Hank Williams, who in his brief life created one of the greatest bodies of work in American music. The film chronicles his rise to fame and its tragic effect on his health and personal life.
Votes: 3,856 | Gross: $1.65M
47. 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: 81,562 | Gross: $42.70M
48. 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.