movies before the 21st century
by moviefanaticgirlsayshi | created - 29 Oct 2019 | updated - 11 Apr 2021 | Public- Instant Watch Options
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1. Picture Perfect (1997)
PG-13 | 101 min | Comedy, Drama, Romance
A young advertising executive's life becomes increasingly complicated when, in order to impress her boss, she pretends to be engaged to a man she has just met.
Director: Glenn Gordon Caron | Stars: Jennifer Aniston, Jay Mohr, Kevin Bacon, Olympia Dukakis
Votes: 21,468 | Gross: $31.06M
2. When Harry Met Sally... (1989)
R | 95 min | Comedy, Drama, Romance
Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.
Director: Rob Reiner | Stars: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby
Votes: 242,894 | Gross: $92.82M
3. Message in a Bottle (1999)
PG-13 | 126 min | Drama, Romance
A woman discovers a tragic love letter in a bottle on a beach, and is determined to track down its author.
Director: Luis Mandoki | Stars: Kevin Costner, Robin Wright, Paul Newman, John Savage
Votes: 40,381 | Gross: $52.88M
4. Cruel Intentions (1999)
R | 97 min | Drama, Romance
Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.
Director: Roger Kumble | Stars: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair
Votes: 205,273 | Gross: $38.77M
5. 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: 31,395 | Gross: $70.10M
6. The Breakfast Club (1985)
R | 97 min | Comedy, Drama
Five high school students meet in Saturday detention and discover how they have a great deal more in common than they thought.
Director: John Hughes | Stars: Emilio Estevez, Judd Nelson, Molly Ringwald, Ally Sheedy
Votes: 436,841 | Gross: $45.88M
7. Wish Upon a Star (1996 TV Movie)
PG | 90 min | Comedy, Family, Fantasy
A younger sister wishes to switch places with her popular older sister and the two bickering siblings awaken to find the wish has come true.
Director: Blair Treu | Stars: Katherine Heigl, Danielle Harris, Donnie Jeffcoat, Scott Wilkinson
Votes: 8,423
8. The Parent Trap (1998)
PG | 128 min | Adventure, Comedy, Drama
Identical twins Annie and Hallie, separated at birth and each raised by one of their biological parents, discover each other for the first time at summer camp and make a plan to bring their wayward parents back together.
Director: Nancy Meyers | Stars: Lindsay Lohan, Dennis Quaid, Natasha Richardson, Elaine Hendrix
Votes: 154,955 | Gross: $66.31M
9. 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: 385,698 | Gross: $38.18M
10. Drive Me Crazy (1999)
PG-13 | 91 min | Comedy, Drama, Romance
Nicole and Chase used to be BFFs, then junior high happened. The high school centennial dance is coming but Nicole gets dumped. So does Chase. They stage a relationship to get at their exes. They visit each other's worlds. Love in the air?
Director: John Schultz | Stars: Melissa Joan Hart, Adrian Grenier, Stephen Collins, Mark Metcalf
Votes: 21,304 | Gross: $17.85M
11. Sixteen Candles (1984)
PG | 93 min | Comedy, Romance
A girl's "sweet" sixteenth birthday is anything but special: her family forgets about it, and she suffers from every embarrassment possible.
Director: John Hughes | Stars: Molly Ringwald, Anthony Michael Hall, Justin Henry, Michael Schoeffling
Votes: 126,452 | Gross: $23.69M
12. The Addams Family (1991)
PG-13 | 99 min | Comedy, Fantasy
Con artists plan to fleece an eccentric family using an accomplice who claims to be their long-lost uncle.
Director: Barry Sonnenfeld | Stars: Anjelica Huston, Raul Julia, Christopher Lloyd, Dan Hedaya
Votes: 180,066 | Gross: $113.50M
13. 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: 95,993 | Gross: $20.78M
14. The Pick-up Artist (1987)
PG-13 | 81 min | Comedy, Crime, Drama
A womanizer meets his match when he falls for a woman in debt to the mafia.
Director: James Toback | Stars: Molly Ringwald, Robert Downey Jr., Dennis Hopper, Danny Aiello
Votes: 7,851 | Gross: $13.29M
15. An Officer and a Gentleman (1982)
R | 124 min | Drama, Romance
A young man must complete his work at a Navy Officer Candidate School to become an aviator, with the help of a tough Gunnery Sergeant and his new girlfriend.
Director: Taylor Hackford | Stars: Richard Gere, Debra Winger, David Keith, Robert Loggia
Votes: 62,649 | Gross: $129.80M
16. Jumanji (1995)
PG | 104 min | Adventure, Comedy, Family
When two kids find and play a magical board game, they release a man trapped in it for decades - and a host of dangers that can only be stopped by finishing the game.
Director: Joe Johnston | Stars: Robin Williams, Kirsten Dunst, Bonnie Hunt, Jonathan Hyde
Votes: 377,155 | Gross: $100.48M
17. 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: 229,790 | Gross: $115.82M
18. Before Sunrise (1995)
R | 101 min | Drama, Romance
A young man and woman meet on a train in Europe, and wind up spending one evening together in Vienna. Unfortunately, both know that this will probably be their only night together.
Director: Richard Linklater | Stars: Ethan Hawke, Julie Delpy, Andrea Eckert, Hanno Pöschl
Votes: 339,602 | Gross: $5.54M
19. 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: 190,972 | Gross: $126.53M
20. 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: 342,511 | Gross: $116.09M
21. The Godfather (1972)
R | 175 min | Crime, Drama
The aging patriarch of an organized crime dynasty transfers control of his clandestine empire to his reluctant son.
Director: Francis Ford Coppola | Stars: Marlon Brando, Al Pacino, James Caan, Diane Keaton
Votes: 2,014,055 | Gross: $134.97M
22. 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: 246,123 | Gross: $56.63M
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