Great Romances of the 21st Century (and 20th)
by badscene | created - 09 Dec 2017 | updated - 5 months ago | Public- Instant Watch Options
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1. 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 forever.
Director: Michel Gondry | Stars: Jim Carrey, Kate Winslet, Tom Wilkinson, Gerry Robert Byrne
Votes: 1,077,522 | Gross: $34.40M
2. The Wedding Singer (1998)
PG-13 | 97 min | Comedy, Music, Romance
Robbie, a singer, and Julia, a waitress, are both engaged, but to the wrong people. Fortune intervenes to help them discover each other.
Director: Frank Coraci | Stars: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert
Votes: 162,227 | Gross: $80.25M
3. Punch-Drunk Love (2002)
R | 95 min | Comedy, Drama, Romance
Socially frustrated Barry Egan calls a phone-sex line to curb his loneliness. Little does he know it will land him in deep trouble and will jeopardize his burgeoning romance with the mysterious Lena.
Director: Paul Thomas Anderson | Stars: Adam Sandler, Emily Watson, Philip Seymour Hoffman, Jason Andrews
Votes: 177,354 | Gross: $17.84M
4. Monster (2003)
R | 109 min | Biography, Crime, Drama
Based on the life of Aileen Wuornos, a Daytona Beach prostitute who became a serial killer.
Director: Patty Jenkins | Stars: Charlize Theron, Christina Ricci, Bruce Dern, Lee Tergesen
Votes: 161,735 | Gross: $34.47M
5. Love Actually (2003)
R | 135 min | Comedy, Drama, Romance
Follows the lives of eight very different couples in dealing with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London, England.
Director: Richard Curtis | Stars: Hugh Grant, Martine McCutcheon, Liam Neeson, Laura Linney
Votes: 531,379 | Gross: $59.70M
6. 500 Days of Summer (2009)
PG-13 | 95 min | Comedy, Drama, Romance
After being dumped by the girl he believes to be his soulmate, hopeless romantic Tom Hansen reflects on their relationship to try and figure out where things went wrong and how he can win her back.
Director: Marc Webb | Stars: Zooey Deschanel, Joseph Gordon-Levitt, Geoffrey Arend, Chloë Grace Moretz
Votes: 557,460 | Gross: $32.39M
7. But I'm a Cheerleader (1999)
R | 85 min | Comedy, Drama, Romance
A naive teenager is sent to rehab camp when her straitlaced parents and friends suspect her of being a lesbian.
Director: Jamie Babbit | Stars: Natasha Lyonne, Clea DuVall, Michelle Williams, Brandt Wille
Votes: 41,188 | Gross: $2.21M
8. The Family Stone (2005)
PG-13 | 103 min | Comedy, Drama, Romance
An uptight, liberal businesswoman accompanies her boyfriend to his eccentric and outgoing family's annual Christmas celebration and finds that she's a fish out of water in their free-spirited way of life.
Director: Thomas Bezucha | Stars: Dermot Mulroney, Sarah Jessica Parker, Claire Danes, Diane Keaton
Votes: 75,204 | Gross: $60.06M
9. The Big Sick (2017)
R | 120 min | Comedy, Drama, Romance
Pakistan-born comedian Kumail Nanjiani and grad student Emily Gardner fall in love but struggle as their cultures clash. When Emily contracts a mysterious illness, Kumail finds himself forced to face her feisty parents, his family's expectations, and his true feelings.
Director: Michael Showalter | Stars: Kumail Nanjiani, Zoe Kazan, Holly Hunter, Ray Romano
Votes: 143,542 | Gross: $42.87M
10. Some Kind of Wonderful (1987)
PG-13 | 95 min | Drama, Romance
When Keith goes out with Amanda, the girl of his dreams, Amanda's ex-boyfriend plans to get back at Keith. Meanwhile, Keith's best friend, tomboy Watts, realizes she has feelings for Keith.
Director: Howard Deutch | Stars: Eric Stoltz, Mary Stuart Masterson, Lea Thompson, Craig Sheffer
Votes: 34,637 | Gross: $18.55M
11. Harold and Maude (1971)
PG | 91 min | Comedy, Drama, Romance
Young, rich, and obsessed with death, Harold finds himself changed forever when he meets lively septuagenarian Maude at a funeral.
Director: Hal Ashby | Stars: Ruth Gordon, Bud Cort, Vivian Pickles, Cyril Cusack
Votes: 81,824
12. Jerry Maguire (1996)
R | 139 min | Comedy, Drama, Romance
When a sports agent has a moral epiphany and is fired for expressing it, he decides to put his new philosophy to the test as an independent agent with the only athlete who stays with him and his former colleague.
Director: Cameron Crowe | Stars: Tom Cruise, Cuba Gooding Jr., Renée Zellweger, Kelly Preston
Votes: 286,920 | Gross: $153.95M
13. 10 Things I Hate About You (1999)
PG-13 | 97 min | Comedy, Drama, Romance
A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.
Director: Gil Junger | Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik
Votes: 384,904 | Gross: $38.18M
14. Garden State (2004)
R | 102 min | Comedy, Drama, Romance
A quietly troubled young man returns home for his mother's funeral after being estranged from his family for a decade.
Director: Zach Braff | Stars: Zach Braff, Peter Sarsgaard, Natalie Portman, Ian Holm
Votes: 223,169 | Gross: $26.78M
15. Titanic (1997)
PG-13 | 194 min | Drama, Romance
A seventeen-year-old aristocrat falls in love with a kind but poor artist aboard the luxurious, ill-fated R.M.S. Titanic.
Director: James Cameron | Stars: Leonardo DiCaprio, Kate Winslet, Billy Zane, Kathy Bates
Votes: 1,279,580 | Gross: $659.33M
16. Friends with Benefits (2011)
R | 109 min | Comedy, Romance
A young man and woman decide to take their friendship to the next level without becoming a couple, but soon discover that adding sex only leads to complications.
Director: Will Gluck | Stars: Mila Kunis, Justin Timberlake, Patricia Clarkson, Jenna Elfman
Votes: 394,406 | Gross: $55.80M
17. Notting Hill (1999)
PG-13 | 124 min | Comedy, Drama, Romance
A set of circumstances makes Anna Scott, a famous actress, fall in love with William Thacker, owner of a bookstore in Notting Hill. But the paparazzi's fascination with her complicates their bond.
Director: Roger Michell | Stars: Hugh Grant, Julia Roberts, Richard McCabe, Rhys Ifans
Votes: 342,089 | Gross: $116.09M
18. Bridget Jones's Diary (2001)
R | 97 min | Comedy, Drama, Romance
Bridget Jones is determined to improve herself while she looks for love in a year in which she keeps a personal diary.
Director: Sharon Maguire | Stars: Renée Zellweger, Colin Firth, Hugh Grant, Gemma Jones
Votes: 263,359 | Gross: $71.54M
19. How to Lose a Guy in 10 Days (2003)
PG-13 | 116 min | Comedy, Romance
Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days.
Director: Donald Petrie | Stars: Kate Hudson, Matthew McConaughey, Adam Goldberg, Kathryn Hahn
Votes: 269,810 | Gross: $105.81M
20. My Big Fat Greek Wedding (2002)
PG | 95 min | Comedy, Drama, Romance
A young Greek woman falls in love with a non-Greek and struggles to get her family to accept him while she comes to terms with her heritage and cultural identity.
Director: Joel Zwick | Stars: Nia Vardalos, John Corbett, Michael Constantine, Christina Eleusiniotis
Votes: 144,572 | Gross: $241.44M
21. Never Been Kissed (1999)
PG-13 | 107 min | Comedy, Drama, Romance
A newspaper reporter enrolls in high school as part of research for a story.
Director: Raja Gosnell | Stars: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon
Votes: 97,527 | Gross: $55.47M
22. Forgetting Sarah Marshall (2008)
R | 111 min | Comedy, Drama, Romance
Devastated Peter takes a Hawaiian vacation in order to deal with the recent break-up with his TV star girlfriend, Sarah. Little does he know, Sarah's traveling to the same resort as her ex - and she's bringing along her new boyfriend.
Director: Nicholas Stoller | Stars: Kristen Bell, Jason Segel, Paul Rudd, Mila Kunis
Votes: 302,373 | Gross: $63.17M
23. The 40-Year-Old Virgin (2005)
R | 116 min | Comedy, Romance
Goaded by his buddies, a nerdy guy who's never "done the deed" only finds the pressure mounting when he meets a single mother.
Director: Judd Apatow | Stars: Steve Carell, Catherine Keener, Paul Rudd, Romany Malco
Votes: 466,768 | Gross: $109.45M
24. Crazy, Stupid, Love. (2011)
PG-13 | 118 min | Comedy, Drama, Romance
A middle-aged husband's life changes dramatically when his wife asks him for a divorce. He seeks to rediscover his manhood with the help of a newfound friend, Jacob, learning to pick up girls at bars.
Directors: Glenn Ficarra, John Requa | Stars: Steve Carell, Ryan Gosling, Julianne Moore, Emma Stone
Votes: 564,097 | Gross: $84.35M
25. Moonrise Kingdom (2012)
PG-13 | 94 min | Adventure, Comedy, Drama
Two 12-year-olds, who live on an island, fall in love with each other and elope into the wilderness. While people set out on a search mission, a violent storm approaching them catches their attention.
Director: Wes Anderson | Stars: Jared Gilman, Kara Hayward, Bruce Willis, Bill Murray
Votes: 366,680 | Gross: $45.51M
26. Clueless (1995)
PG-13 | 97 min | Comedy, Romance
Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other.
Director: Amy Heckerling | Stars: Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd
Votes: 245,680 | Gross: $56.63M
27. The Fault in Our Stars (2014)
PG-13 | 126 min | Drama, Romance
Hazel and Gus are teenagers who meet at a cancer support group and fall in love. They both share the same acerbic wit and a love of books, especially "An Imperial Affliction", so they embark on a journey to visit an author in Amsterdam.
Director: Josh Boone | Stars: Shailene Woodley, Ansel Elgort, Nat Wolff, Laura Dern
Votes: 401,007 | Gross: $124.87M
28. Say Anything (1989)
PG-13 | 100 min | Comedy, Drama, Romance
A noble underachiever and a beautiful valedictorian fall in love the summer before she goes off to college.
Director: Cameron Crowe | Stars: John Cusack, Ione Skye, John Mahoney, Lili Taylor
Votes: 95,886 | Gross: $20.78M
29. Just Like Heaven (2005)
PG-13 | 95 min | Comedy, Drama, Fantasy
A lonely landscape architect falls for the spirit of the beautiful woman who used to live in his new apartment.
Director: Mark Waters | Stars: Reese Witherspoon, Mark Ruffalo, Donal Logue, Dina Spybey-Waters
Votes: 117,325 | Gross: $48.32M
30. Ghost (1990)
PG-13 | 127 min | Drama, Fantasy, Romance
After a young man is murdered, his spirit stays behind to warn his lover of impending danger, with the help of a reluctant psychic.
Director: Jerry Zucker | Stars: Patrick Swayze, Demi Moore, Whoopi Goldberg, Tony Goldwyn
Votes: 235,833 | Gross: $217.63M
31. Like Crazy (2011)
PG-13 | 86 min | Drama, Romance
A British college student falls for an American student, only to be separated from him when she's banned from the U.S. after overstaying her visa.
Director: Drake Doremus | Stars: Felicity Jones, Anton Yelchin, Jennifer Lawrence, Charlie Bewley
Votes: 63,292 | Gross: $3.41M
32. Forget Paris (1995)
PG-13 | 101 min | Comedy, Romance
Mickey, an NBA referee, meets Ellen, an American airline official, in Paris. It develops into a relationship of ups and downs.
Director: Billy Crystal | Stars: Billy Crystal, Debra Winger, Joe Mantegna, Cynthia Stevenson
Votes: 13,064 | Gross: $33.19M
33. Latter Days (2003)
R | 107 min | Comedy, Drama, Romance
A promiscuous gay party animal falls for a young Mormon missionary, leading to crisis, cliché, and catastrophe.
Director: C. Jay Cox | Stars: Wes Ramsey, Steve Sandvoss, Mary Kay Place, Amber Benson
Votes: 18,573 | Gross: $0.82M
34. Can't Hardly Wait (1998)
PG-13 | 100 min | Comedy, Romance
A complete graduating class, consisting of beautiful girls, geeks and promising footballers, assemble at a rich classmate's residence for a party. Interesting developments follow at the get-together.
Directors: Harry Elfont, Deborah Kaplan | Stars: Jennifer Love Hewitt, Ethan Embry, Charlie Korsmo, Lauren Ambrose
Votes: 53,955 | Gross: $25.34M
35. Minnie and Moskowitz (1971)
GP | 114 min | Comedy, Drama, Romance
A museum curator falls in love with a crazy parking attendant.
Director: John Cassavetes | Stars: Gena Rowlands, Seymour Cassel, Val Avery, Timothy Carey
Votes: 5,281
36. Ali: Fear Eats the Soul (1974)
Not Rated | 92 min | Drama, Romance
A lonely widow meets a much younger Moroccan worker in a bar during a rainstorm. They fall in love, to their own surprise and to the outright shock of their families, colleagues, and drinking buddies.
Director: Rainer Werner Fassbinder | Stars: Brigitte Mira, El Hedi ben Salem, Barbara Valentin, Irm Hermann
Votes: 23,843
37. The Girl Next Door (2004)
R | 109 min | Comedy, Drama, Romance
A teenager's dreams come true when a former porn star moves in next door and they fall in love.
Director: Luke Greenfield | Stars: Emile Hirsch, Nicholas Downs, Elisha Cuthbert, Timothy Olyphant
Votes: 239,525 | Gross: $14.59M
38. Just Friends (I) (2005)
PG-13 | 96 min | Comedy, Romance
While visiting his hometown during Christmas, a man comes face-to-face with his old high-school crush and best friend--a woman whose rejection of him turned him into a ferocious womanizer.
Director: Roger Kumble | Stars: Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein
Votes: 127,249 | Gross: $32.62M
39. Milk Money (1994)
PG-13 | 110 min | Comedy, Romance
A group of young boys befriend a prostitute named V.
Director: Richard Benjamin | Stars: Melanie Griffith, Ed Harris, Michael Patrick Carter, Malcolm McDowell
Votes: 13,075 | Gross: $18.14M
40. The Holiday (2006)
PG-13 | 136 min | Comedy, Romance
Two women troubled with guy-problems swap homes in each other's countries, where they each meet a local guy and fall in love.
Director: Nancy Meyers | Stars: Kate Winslet, Cameron Diaz, Jude Law, Jack Black
Votes: 322,845 | Gross: $63.22M
41. The Spectacular Now (2013)
R | 95 min | Drama, Romance
A hard-partying high school senior's philosophy on life changes when he meets the not-so-typical "nice girl."
Director: James Ponsoldt | Stars: Miles Teller, Shailene Woodley, Kyle Chandler, Jennifer Jason Leigh
Votes: 161,341 | Gross: $6.85M
42. Pariah (I) (2011)
R | 86 min | Drama
A Brooklyn teenager juggles conflicting identities and risks friendship, heartbreak and family in a desperate search for sexual expression.
Director: Dee Rees | Stars: Adepero Oduye, Kim Wayans, Aasha Davis, Pernell Walker
Votes: 7,551 | Gross: $0.76M
43. The One I Love (2014)
R | 91 min | Comedy, Drama, Fantasy
A troubled couple vacate to a beautiful getaway, but bizarre circumstances further complicate their situation.
Director: Charlie McDowell | Stars: Mark Duplass, Elisabeth Moss, Ted Danson, Kiana Cason
Votes: 43,505 | Gross: $0.51M
44. Boomerang (1992)
R | 117 min | Comedy, Drama, Romance
A successful executive and womanizer finds his lifestyle choices have turned back on him when his new female boss turns out to be an even bigger deviant than he is.
Director: Reginald Hudlin | Stars: Eddie Murphy, Robin Givens, Halle Berry, David Alan Grier
Votes: 31,362 | Gross: $70.10M
45. Chocolat (2000)
PG-13 | 121 min | Drama, Romance
A French woman and her young daughter open up a chocolate shop in a small remote village that shakes up the rigid morality of the community.
Director: Lasse Hallström | Stars: Juliette Binoche, Johnny Depp, Judi Dench, Alfred Molina
Votes: 201,914 | Gross: $71.51M
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