Sort by Popularity - Most Popular Movies and TV Shows tagged with keyword "older-woman-younger-man-relationship"

51. Atlantis: The Lost Empire (2001)

PG | 95 min | Animation, Action, Adventure

A young linguist named Milo Thatch joins an intrepid group of explorers to find the mysterious lost continent of Atlantis.

Directors: Gary Trousdale, Kirk Wise | Stars: Michael J. Fox, Jim Varney, Corey Burton, Claudia Christian

Votes: 134,536 | Gross: $84.05M

52. The L Word (I) (2004–2009)

TV-MA | 50 min | Drama, Romance

Follows the lives and loves of a small, close-knit group of lesbian women living in Los Angeles as well as the friends and family members that either support or loathe them.

Stars: Jennifer Beals, Leisha Hailey, Laurel Holloman, Mia Kirshner

Votes: 28,833

53. The Last American Virgin (1982)

R | 92 min | Comedy, Drama, Romance

Pizza delivery boy Gary, loudmouth David and hunky Rick are three high school students out to lose their virginity any way they can. Gary falls for transfer student Karen, who gets involved with Rick.

Director: Boaz Davidson | Stars: Lawrence Monoson, Diane Franklin, Steve Antin, Joe Rubbo

Votes: 9,818 | Gross: $5.83M

54. The White Queen (2013)

TV-MA | 60 min | Drama, History, Romance

Three different, yet equally relentless women vie for the throne in 15th-century England.

Stars: Aneurin Barnard, Rebecca Ferguson, Amanda Hale, Faye Marsay

Votes: 31,510

55. Girls Trip (2017)

R | 122 min | Adventure, Comedy, Drama

When four lifelong friends travel to New Orleans for the annual Essence Festival, sisterhoods are rekindled, wild sides are rediscovered, and there's enough dancing, drinking, brawling and romancing to make the Big Easy blush.

Director: Malcolm D. Lee | Stars: Regina Hall, Queen Latifah, Jada Pinkett Smith, Tiffany Haddish

Votes: 40,676 | Gross: $115.17M

56. 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.

Director: Paul Thomas Anderson | Stars: Vicky Krieps, Daniel Day-Lewis, Lesley Manville, Julie Vollono

Votes: 145,980 | Gross: $21.02M

57. Mrs. Harris Goes to Paris (2022)

PG | 115 min | Comedy, Drama

A widowed cleaning lady in 1950s London falls madly in love with a couture Dior dress, and decides that she must have one of her own.

Director: Anthony Fabian | Stars: Lesley Manville, Isabelle Huppert, Lambert Wilson, Alba Baptista

Votes: 26,641

58. Good Luck to You, Leo Grande (2022)

R | 97 min | Comedy, Drama

Nancy Stokes, a retired school teacher, is yearning for some adventure, and some sex. And she has a plan, which involves hiring a young sex worker named Leo Grande.

Director: Sophie Hyde | Stars: Emma Thompson, Daryl McCormack, Isabella Laughland, Les Mabaleka

Votes: 38,005

59. Detroit Rock City (1999)

R | 95 min | Adventure, Comedy, Music

In 1978, four rebellious teenagers try to scam their way into a KISS concert.

Director: Adam Rifkin | Stars: Edward Furlong, Giuseppe Andrews, James DeBello, Sam Huntington

Votes: 41,420 | Gross: $4.22M

60. You Don't Mess with the Zohan (2008)

PG-13 | 113 min | Action, Comedy

An Israeli Special Forces Soldier fakes his death so he can re-emerge in New York City as a hair stylist.

Director: Dennis Dugan | Stars: Adam Sandler, John Turturro, Emmanuelle Chriqui, Nick Swardson

Votes: 214,675 | Gross: $100.02M

61. Sunset Boulevard (1950)

Passed | 110 min | Drama, Film-Noir

A screenwriter develops a dangerous relationship with a faded film star determined to make a triumphant return.

Director: Billy Wilder | Stars: William Holden, Gloria Swanson, Erich von Stroheim, Nancy Olson

Votes: 237,031

62. The Paperboy (2012)

R | 107 min | Crime, Drama, Mystery

A reporter returns to his Florida hometown to investigate a case involving a death row inmate.

Director: Lee Daniels | Stars: Matthew McConaughey, Nicole Kidman, John Cusack, Zac Efron

Votes: 39,750 | Gross: $0.69M

63. Cocktail (1988)

R | 104 min | Comedy, Drama, Romance

A talented New York City bartender takes a job at a bar in Jamaica and falls in love.

Director: Roger Donaldson | Stars: Tom Cruise, Bryan Brown, Elisabeth Shue, Lisa Banes

Votes: 92,107 | Gross: $78.22M

64. American Pie 2 (2001)

R | 108 min | Comedy

Jim and his friends are now in college, and they decide to meet up at the beach house for some fun.

Director: J.B. Rogers | Stars: Jason Biggs, Seann William Scott, Shannon Elizabeth, Alyson Hannigan

Votes: 270,745 | Gross: $145.10M

65. Something's Gotta Give (2003)

PG-13 | 128 min | Comedy, Drama, Romance

A swinger on the cusp of being a senior citizen with a taste for young women falls in love with an accomplished woman closer to his age.

Director: Nancy Meyers | Stars: Jack Nicholson, Diane Keaton, Keanu Reeves, Amanda Peet

Votes: 129,461 | Gross: $124.73M

66. Kingpin (1996)

PG-13 | 114 min | Comedy, Sport

A star bowler whose career was prematurely "cut off" hopes to ride a new prodigy to success and riches.

Directors: Bobby Farrelly, Peter Farrelly | Stars: Woody Harrelson, Randy Quaid, Bill Murray, Vanessa Angel

Votes: 91,254 | Gross: $24.94M

67. 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 North Texas town that is slowly dying, both culturally and economically.

Director: Peter Bogdanovich | Stars: Timothy Bottoms, Jeff Bridges, Cybill Shepherd, Ben Johnson

Votes: 52,547 | Gross: $29.13M

68. A Nightmare on Elm Street 3: Dream Warriors (1987)

R | 96 min | Fantasy, Horror

A psychiatrist familiar with knife-wielding dream demon Freddy Krueger helps teens at a mental hospital battle the killer who is invading their dreams.

Director: Chuck Russell | Stars: Heather Langenkamp, Robert Englund, Craig Wasson, Patricia Arquette

Votes: 90,651 | Gross: $44.79M

69. The Little Hours (2017)

R | 89 min | Comedy, Romance

In the Middle Ages, a young servant fleeing from his master takes refuge at a convent full of emotionally unstable nuns. Introduced as a deaf mute man, he must fight to hold his cover as the nuns try to resist temptation.

Director: Jeff Baena | Stars: Alison Brie, Dave Franco, Kate Micucci, Aubrey Plaza

Votes: 25,543 | Gross: $1.65M

70. Sweet Bird of Youth (1962)

Approved | 120 min | Drama, Romance

A drifter and a faded film star, both traumatized by Hollywood, arrive to the guy's hometown, where the old bitter memories revive again.

Director: Richard Brooks | Stars: Paul Newman, Geraldine Page, Shirley Knight, Ed Begley

Votes: 8,503

71. American Wedding (2003)

R | 96 min | Comedy

It's the wedding of Jim and Michelle and the gathering of their families and friends, including Jim's old friends from high school and Michelle's little sister.

Director: Jesse Dylan | Stars: Jason Biggs, Alyson Hannigan, Seann William Scott, Eugene Levy

Votes: 217,597 | Gross: $104.57M

72. A Bigger Splash (2015)

R | 125 min | Drama, Music, Thriller

A famous rock star's vacation in Italy with her boyfriend is disrupted by the unexpected visit of an old friend and his daughter.

Director: Luca Guadagnino | Stars: Tilda Swinton, Matthias Schoenaerts, Ralph Fiennes, Dakota Johnson

Votes: 33,058 | Gross: $1.98M

73. Witness for the Prosecution (1957)

Approved | 116 min | Crime, Drama, Mystery

A veteran British barrister must defend his client in a murder trial that has surprise after surprise.

Director: Billy Wilder | Stars: Tyrone Power, Marlene Dietrich, Charles Laughton, Elsa Lanchester

Votes: 138,392 | Gross: $8.18M

74. Notes on a Scandal (2006)

R | 92 min | Crime, Drama, Romance

A veteran high school teacher befriends a younger art teacher, who is having an affair with one of her fifteen-year-old students. However, her intentions with this new "friend" also go well beyond a platonic friendship.

Director: Richard Eyre | Stars: Cate Blanchett, Judi Dench, Andrew Simpson, Tom Georgeson

Votes: 84,760 | Gross: $17.51M

75. Screwballs (1983)

R | 80 min | Comedy

Frolicking youth comedy about zany high school students set in the 1960s.

Director: Rafal Zielinski | Stars: Peter Keleghan, Kent Deuters, Linda Speciale, Alan Deveau

Votes: 3,681 | Gross: $2.08M

76. Shampoo (1975)

R | 110 min | Comedy, Drama

On Election Day, 1968, a hairdresser and ladies' man is too busy cutting hair and dealing with his various girlfriends and his mistress, whose husband he meets and finds out is having an affair with his ex-girlfriend.

Director: Hal Ashby | Stars: Warren Beatty, Julie Christie, Goldie Hawn, Lee Grant

Votes: 14,234 | Gross: $49.41M

77. Bull Durham (1988)

R | 108 min | Comedy, Romance, Sport

A fan who has an affair with one minor-league baseball player each season meets an up-and-coming pitcher and the experienced catcher assigned to him.

Director: Ron Shelton | Stars: Kevin Costner, Susan Sarandon, Tim Robbins, Trey Wilson

Votes: 59,585 | Gross: $50.89M

78. Only Lovers Left Alive (2013)

R | 123 min | Comedy, Drama, Fantasy

A depressed musician reunites with his lover. However, their romance, which has already endured several centuries, is disrupted by the arrival of her uncontrollable younger sister.

Director: Jim Jarmusch | Stars: Tilda Swinton, Tom Hiddleston, Mia Wasikowska, John Hurt

Votes: 108,400 | Gross: $1.88M

79. Ken Park (2002)

Not Rated | 93 min | Drama

Ken Park is about several Californian skateboarders' lives and relationships with and without their parents.

Directors: Larry Clark, Edward Lachman | Stars: Adam Chubbuck, James Bullard, Seth Gray, Eddie Daniels

Votes: 30,849

80. A Family Affair (II) (2024)

PG-13 | Comedy, Romance | Completed

An unexpected romance triggers comic consequences for a young woman, her mother, and her boss, grappling with the complications of love, sex, and identity.

Director: Richard LaGravenese | Stars: Joey King, Zac Efron, Nicole Kidman, Kathy Bates

81. Juice (1992)

R | 95 min | Action, Crime, Drama

Four inner-city teenagers get caught up in the pursuit of power and happiness, which they refer to as "the juice".

Director: Ernest R. Dickerson | Stars: Omar Epps, Tupac Shakur, Jermaine Hopkins, Khalil Kain

Votes: 30,480 | Gross: $20.15M

82. The Beverly Hillbillies (1993)

PG | 92 min | Comedy, Family

Nice guy redneck Jed Clampett strikes it rich when he finds black oil. He and his kin move to posh Beverly Hills.

Director: Penelope Spheeris | Stars: Diedrich Bader, Erika Eleniak, Jim Varney, Cloris Leachman

Votes: 19,870 | Gross: $44.03M

83. The Garden of Words (2013)

TV-14 | 46 min | Animation, Drama, Romance

On a rainy morning in Tokyo, 15-year-old Takao, an aspiring shoemaker, decides to skip class to sketch designs in a beautiful garden. This is where he meets Yukari, a beautiful yet mysterious woman. They strike an unlikely friendship.

Director: Makoto Shinkai | Stars: Miyu Irino, Kana Hanazawa, Fumi Hirano, Gou Maeda

Votes: 52,894

84. Three Identical Strangers (2018)

PG-13 | 96 min | Documentary, Biography, Drama

In 1980 New York, three young men who were all adopted meet each other and find out they're triplets who were separated at birth. But their quest to find out why turns into a bizarre and sinister mystery.

Director: Tim Wardle | Stars: Robert Shafran, Michael Domnitz, Howard Schneider, Ellen Cervone

Votes: 40,186 | Gross: $12.32M

85. Hall Pass (2011)

R | 105 min | Comedy, Romance

Rick and Fred, two husbands who are having difficulty in their marriages, are given a Hall Pass by their wives: for one week, they can do whatever they want.

Directors: Bobby Farrelly, Peter Farrelly | Stars: Owen Wilson, Jason Sudeikis, Christina Applegate, Jenna Fischer

Votes: 131,234 | Gross: $45.06M

86. Dangerous Liaisons (1988)

R | 119 min | Drama, Romance

A scheming widow and her manipulative ex-lover make a bet regarding the corruption of a recently married woman.

Director: Stephen Frears | Stars: Glenn Close, John Malkovich, Michelle Pfeiffer, Swoosie Kurtz

Votes: 75,309 | Gross: $34.70M

87. Bernie (2011)

PG-13 | 104 min | Biography, Comedy, Crime

In small-town Texas, an affable mortician strikes up a friendship with a wealthy widow, though when she starts to become controlling, he goes to great lengths to separate himself from her grasp.

Director: Richard Linklater | Stars: Jack Black, Shirley MacLaine, Matthew McConaughey, Brady Coleman

Votes: 63,655 | Gross: $9.20M

88. Out of the Blue (II) (2022)

R | 104 min | Crime, Drama, Mystery

Connor, a man whose dull life is transformed into a thrilling fantasy world thanks to the seductive Marilyn.

Director: Neil LaBute | Stars: Diane Kruger, Ray Nicholson, Gia Crovatin, Hank Azaria

Votes: 1,423

89. All About Eve (1950)

Passed | 138 min | Drama

A seemingly timid but secretly ruthless ingénue insinuates herself into the lives of an aging Broadway star and her circle of theater friends.

Director: Joseph L. Mankiewicz | Stars: Bette Davis, Anne Baxter, George Sanders, Celeste Holm

Votes: 139,085 | Gross: $0.01M

90. Tender Cousins (1980)

R | 90 min | Comedy, Drama, Romance

With Adolf Hitler threatening Europe, against the backdrop of the deceptively peaceful summer of 1939, 14-year-old Julien experiences the intoxicating effects of first love, smitten with his beautiful 16-year-old cousin Julia.

Director: David Hamilton | Stars: Thierry Tevini, Anja Schüte, Valérie Dumas, Évelyne Dandry

Votes: 2,176

91. Wild Orchid (1989)

R | 105 min | Drama, Romance

A female lawyer becomes mesmerized by a self-made millionaire during an encounter in Rio setting off a series of erotic encounters.

Director: Zalman King | Stars: Mickey Rourke, Jacqueline Bisset, Carré Otis, Assumpta Serna

Votes: 12,952 | Gross: $11.06M

92. American Gigolo (1980)

R | 117 min | Crime, Drama, Mystery

A Los Angeles escort is accused of a murder which he did not commit.

Director: Paul Schrader | Stars: Richard Gere, Lauren Hutton, Hector Elizondo, Nina van Pallandt

Votes: 29,564 | Gross: $23.00M

93. Spread (2009)

R | 97 min | Comedy, Drama, Romance

A drama centered on a serial womanizer and his jilted lover.

Director: David Mackenzie | Stars: Ashton Kutcher, Anne Heche, Margarita Levieva, Sebastian Stan

Votes: 41,939 | Gross: $0.25M

94. Empire of Light (2022)

R | 115 min | Drama, Romance

A drama about the power of human connection during turbulent times, set in an English coastal town in the early 1980s.

Director: Sam Mendes | Stars: Olivia Colman, Micheal Ward, Colin Firth, Toby Jones

Votes: 24,389

95. The Squid and the Whale (2005)

R | 81 min | Comedy, Drama

Follows two young boys dealing with their parents' divorce in Brooklyn in the 1980s.

Director: Noah Baumbach | Stars: Owen Kline, Jeff Daniels, Laura Linney, Jesse Eisenberg

Votes: 90,649 | Gross: $7.36M

96. Class (1983)

R | 98 min | Comedy, Drama, Romance

A young man in private school spends one crazy night out, and only later does he learn more about the woman who enlivened his night.

Director: Lewis John Carlino | Stars: Jacqueline Bisset, Rob Lowe, Andrew McCarthy, Cliff Robertson

Votes: 12,163

97. Youngblood (1986)

R | 110 min | Drama, Romance, Sport

A 17 year old farm boy is offered an ice hockey tryout. His brother drives him to Canada. He has fast legs, slow fists, but is chosen. Will he learn to use his fists and play ice hockey the Canuck way? Will he get the coach's cute daughter?

Director: Peter Markle | Stars: Rob Lowe, Cynthia Gibb, Patrick Swayze, Ed Lauter

Votes: 15,891 | Gross: $15.45M

98. Timer (2009)

R | 99 min | Comedy, Drama, Romance

If a clock could count down to the moment you meet your soul mate, would you want to know?

Director: Jac Schaeffer | Stars: Emma Caulfield Ford, Scott Holroyd, Kali Rocha, Katie Von Till

Votes: 13,514

99. The War Zone (1999)

R | 98 min | Drama, Thriller

An alienated teenager, saddened that he has moved away from London, must find a way to deal with a dark family secret.

Director: Tim Roth | Stars: Ray Winstone, Annabelle Apsion, Kate Ashfield, Lara Belmont

Votes: 11,242 | Gross: $0.25M

100. Lady Vengeance (2005)

R | 115 min | Crime, Drama, Thriller

After being wrongfully imprisoned for thirteen years and having her child taken away from her, a woman seeks revenge through increasingly brutal means.

Director: Park Chan-wook | Stars: Nam-mi Kang, Jeong-nam Choi, Hye-Sook Go, Bok-hwa Baek

Votes: 86,338 | Gross: $0.21M