Romance late 90s
by patyn | created - 23 Jul 2021 | updated - 6 months ago | Public- Instant Watch Options
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1. Breakfast at Tiffany's (1961)
Approved | 115 min | Comedy, Drama, Romance
A young New York socialite becomes interested in a young man who has moved into her apartment building, but her past threatens to get in the way.
Director: Blake Edwards | Stars: Audrey Hepburn, George Peppard, Patricia Neal, Buddy Ebsen
Votes: 192,143
2. Sleepless in Seattle (1993)
PG | 105 min | Comedy, Drama, Romance
A recently widowed man's son calls a radio talk-show in an attempt to find his father a partner.
Director: Nora Ephron | Stars: Tom Hanks, Meg Ryan, Ross Malinger, Rita Wilson
Votes: 190,843 | Gross: $126.53M
3. Lost in Translation (2003)
R | 102 min | Comedy, Drama
A faded movie star and a neglected young woman form an unlikely bond after crossing paths in Tokyo.
Director: Sofia Coppola | Stars: Bill Murray, Scarlett Johansson, Giovanni Ribisi, Anna Faris
Votes: 488,951 | Gross: $44.59M
4. 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: 385,197 | Gross: $38.18M
5. You've Got Mail (1998)
PG | 119 min | Comedy, Drama, Romance
Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet, both blissfully unaware that he's trying to put her out of business.
Director: Nora Ephron | Stars: Tom Hanks, Meg Ryan, Greg Kinnear, Parker Posey
Votes: 229,634 | Gross: $115.82M
6. 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: 531,496 | Gross: $59.70M
7. Moonstruck (1987)
PG | 102 min | Comedy, Drama, Romance
Loretta Castorini, a bookkeeper from Brooklyn, New York, finds herself in a difficult situation when she falls for the brother of the man she has agreed to marry.
Director: Norman Jewison | Stars: Cher, Nicolas Cage, Olympia Dukakis, Danny Aiello
Votes: 68,459 | Gross: $80.64M
8. Sweet Home Alabama (2002)
PG-13 | 108 min | Comedy, Romance
A young woman who has reinvented herself as a New York City socialite must return home to Alabama to obtain a divorce from her husband after seven years of separation.
Director: Andy Tennant | Stars: Reese Witherspoon, Patrick Dempsey, Josh Lucas, Candice Bergen
Votes: 123,575 | Gross: $127.22M
9. 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: 269,963 | Gross: $105.81M
10. 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.
Director: Adam Brooks | Stars: Ryan Reynolds, Rachel Weisz, Abigail Breslin, An Nguyen
Votes: 173,246 | Gross: $31.97M
11. 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: 342,236 | Gross: $116.09M
12. Chasing Liberty (2004)
PG-13 | 111 min | Comedy, Romance
Anna wants to be like other girls her age (18): date a guy etc. but she's the US president's daughter and always guarded. In Prague he breaks his promise of only 2 agents following her to a concert and she runs away with Ben to see Europe.
Director: Andy Cadiff | Stars: Mandy Moore, Matthew Goode, Mark Harmon, Stark Sands
Votes: 41,062 | Gross: $12.19M
13. Christmas Mail (2010)
TV-PG | 89 min | Comedy, Drama, Family
In this holiday romantic comedy, a mysterious woman who works at the post office answering Santa's mail captures the heart of a disillusioned postal carrier
Director: John Murlowski | Stars: Ashley Scott, A.J. Buckley, Lochlyn Munro, Rolonda Watts
Votes: 1,952
14. 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: 13,078 | Gross: $18.14M
15. What Happens in Vegas (2008)
PG-13 | 99 min | Comedy, Romance
A man and a woman are compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.
Director: Tom Vaughan | Stars: Cameron Diaz, Ashton Kutcher, Rob Corddry, Lake Bell
Votes: 187,866 | Gross: $80.28M
16. 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: 322,940 | Gross: $63.22M
17. New Year's Eve (2011)
PG-13 | 118 min | Comedy, Romance
The lives of several couples and singles in New York City intertwine over the course of New Year's Eve.
Director: Garry Marshall | Stars: Sarah Jessica Parker, Jessica Biel, Ashton Kutcher, Michelle Pfeiffer
Votes: 89,858 | Gross: $54.54M
18. Heartbreakers (2001)
PG-13 | 123 min | Comedy, Crime, Romance
A mother and daughter con team seduce and scam wealthy men.
Director: David Mirkin | Stars: Sigourney Weaver, Jennifer Love Hewitt, Gene Hackman, Ray Liotta
Votes: 57,985 | Gross: $40.34M
19. Life or Something Like It (2002)
PG-13 | 103 min | Comedy, Romance
A reporter interviews a psychic, who tells her that she's going to die and her life is meaningless.
Director: Stephen Herek | Stars: Angelina Jolie, Edward Burns, Tony Shalhoub, Christian Kane
Votes: 28,099 | Gross: $14.45M
20. Reality Bites (1994)
PG-13 | 99 min | Comedy, Drama, Romance
A documentary filmmaker and her fellow Generation X graduates face life after college, looking for work and love in Houston.
Director: Ben Stiller | Stars: Winona Ryder, Ethan Hawke, Janeane Garofalo, Steve Zahn
Votes: 53,637 | Gross: $20.98M
21. Free Rein (2017–2019)
TV-G | 26 min | Action, Adventure, Comedy
After befriending a mysterious horse during a summer in the English countryside, 15-year-old Zoe finds the strength to deal with issues she faces.
Stars: Freddy Carter, Jaylen Barron, Manpreet Bambra, Celine Buckens
Votes: 2,513
22. Groundhog Day (1993)
PG | 101 min | Comedy, Drama, Fantasy
A narcissistic, self-centered weatherman finds himself in a time loop on Groundhog Day.
Director: Harold Ramis | Stars: Bill Murray, Andie MacDowell, Chris Elliott, Stephen Tobolowsky
Votes: 685,037 | Gross: $70.91M
23. Legally Blonde (2001)
PG-13 | 96 min | Comedy, Romance
Elle Woods, a fashionable sorority queen, is dumped by her boyfriend. She decides to follow him to law school. While she is there, she figures out that there is more to her than just looks.
Director: Robert Luketic | Stars: Reese Witherspoon, Luke Wilson, Selma Blair, Matthew Davis
Votes: 248,102 | Gross: $96.52M
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