90s

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1. The Cutting Edge (1992)

PG | 101 min | Comedy, Drama, Romance

A temperamental figure skater and a former hockey player try to win Olympic gold as a figure skating pairs team.

Director: Paul Michael Glaser | Stars: D.B. Sweeney, Moira Kelly, Roy Dotrice, Terry O'Quinn

Votes: 17,554 | Gross: $25.11M

2. Reality Bites (1994)

PG-13 | 99 min | Comedy, Drama, Romance

67 Metascore

A documentary filmmaker and her fellow Gen 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: 42,214 | Gross: $20.98M

3. Mermaids (1990)

PG-13 | 110 min | Comedy, Drama, Romance

56 Metascore

An unconventional single mother relocates with her two daughters to a small Massachusetts town in 1963, where a number of events and relationships both challenge and strengthen their familial bonds.

Director: Richard Benjamin | Stars: Cher, Bob Hoskins, Winona Ryder, Michael Schoeffling

Votes: 26,255 | Gross: $35.42M

4. Four Weddings and a Funeral (1994)

R | 117 min | Comedy, Drama, Romance

81 Metascore

Over the course of five social occasions, a committed bachelor must consider the notion that he may have discovered love.

Director: Mike Newell | Stars: Hugh Grant, Andie MacDowell, James Fleet, Simon Callow

Votes: 126,797 | Gross: $52.70M

5. Drive Me Crazy (1999)

PG-13 | 91 min | Comedy, Drama, Romance

42 Metascore

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: 17,005 | Gross: $17.85M

6. She's All That (1999)

PG-13 | 95 min | Comedy, Romance

51 Metascore

A high school jock makes a bet that he can turn an unattractive girl into the school's prom queen.

Director: Robert Iscove | Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker

Votes: 78,430 | Gross: $63.37M

7. Before Sunrise (1995)

R | 101 min | Drama, Romance

77 Metascore

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: 238,753 | Gross: $5.54M

8. Jersey Girl (1992)

PG-13 | 95 min | Comedy, Drama, Romance

Sal is a wealthy and triumphant yuppie who normaly would not do everything in order to get a woman. But this time it is something special and he is about to give up his position for his ... See full summary »

Director: David Burton Morris | Stars: Jami Gertz, Dylan McDermott, Sheryl Lee, Aida Turturro

Votes: 1,348

9. While You Were Sleeping (1995)

PG | 103 min | Comedy, Drama, Romance

67 Metascore

A hopeless romantic Chicago Transit Authority token collector is mistaken for the fiancée of a coma patient.

Director: Jon Turteltaub | Stars: Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle

Votes: 84,386 | Gross: $81.06M

10. Groundhog Day (1993)

PG | 101 min | Comedy, Fantasy, Romance

72 Metascore

A weatherman finds himself inexplicably living the same day over and over again.

Director: Harold Ramis | Stars: Bill Murray, Andie MacDowell, Chris Elliott, Stephen Tobolowsky

Votes: 542,358 | Gross: $70.91M

11. Clueless (1995)

PG-13 | 97 min | Comedy, Romance

68 Metascore

A rich high school student tries to boost a new pupil's popularity, but reckons without affairs of the heart getting in the way.

Director: Amy Heckerling | Stars: Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd

Votes: 157,251 | Gross: $56.63M

12. Never Been Kissed (1999)

PG-13 | 107 min | Comedy, Drama, Romance

60 Metascore

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: 77,731 | Gross: $55.47M

13. Picture Perfect (1997)

PG-13 | 105 min | Comedy, Drama, Romance

44 Metascore

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: 17,882 | Gross: $31.06M

14. Kuch Kuch Hota Hai (1998)

Not Rated | 177 min | Comedy, Drama, Musical

During their college years, Anjali was in love with her best-friend Rahul, but he had eyes only for Tina. Years later, Rahul and the now-deceased Tina's eight-year-old daughter attempts to reunite her father and Anjali.

Director: Karan Johar | Stars: Shah Rukh Khan, Kajol, Rani Mukerji, Sana Saeed

Votes: 43,362 | Gross: $2.10M

15. Strictly Ballroom (1992)

PG | 94 min | Comedy, Drama, Music

72 Metascore

A maverick dancer risks his career by performing an unusual routine and sets out to succeed with a new partner.

Director: Baz Luhrmann | Stars: Paul Mercurio, Tara Morice, Bill Hunter, Pat Thomson

Votes: 23,313 | Gross: $11.74M

16. 10 Things I Hate About You (1999)

PG-13 | 97 min | Comedy, Drama, Romance

70 Metascore

A pretty, popular teenager can't go out on a date until her ill-tempered older sister does.

Director: Gil Junger | Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik

Votes: 270,336 | Gross: $38.18M

17. What's Eating Gilbert Grape (1993)

PG-13 | 118 min | Drama

73 Metascore

After his father's death, Gilbert has to care for his mentally-disabled brother, Arnie, and his morbidly obese mother. This situation is suddenly challenged though, when love unexpectedly walks into his life.

Director: Lasse Hallström | Stars: Johnny Depp, Leonardo DiCaprio, Juliette Lewis, Mary Steenburgen

Votes: 197,606 | Gross: $9.17M

18. Election (1999)

R | 103 min | Comedy, Drama, Romance

83 Metascore

A high school teacher's personal life becomes complicated as he works with students during the school elections, particularly with an obsessive overachiever determined to become student body president.

Director: Alexander Payne | Stars: Matthew Broderick, Reese Witherspoon, Chris Klein, Jessica Campbell

Votes: 83,230 | Gross: $14.88M

19. Girl, Interrupted (1999)

R | 127 min | Biography, Drama

51 Metascore

Based on writer Susanna Kaysen's account of her 18-month stay at a mental hospital in the late 1960s.

Director: James Mangold | Stars: Winona Ryder, Angelina Jolie, Clea DuVall, Brittany Murphy

Votes: 147,780 | Gross: $28.87M

20. Good Will Hunting (1997)

R | 126 min | Drama, Romance

70 Metascore

Will Hunting, a janitor at M.I.T., has a gift for mathematics, but needs help from a psychologist to find direction in his life.

Director: Gus Van Sant | Stars: Robin Williams, Matt Damon, Ben Affleck, Stellan Skarsgård

Votes: 769,696 | Gross: $138.43M

21. Jerry Maguire (1996)

R | 139 min | Comedy, Drama, Romance

77 Metascore

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 secretary.

Director: Cameron Crowe | Stars: Tom Cruise, Cuba Gooding Jr., Renée Zellweger, Kelly Preston

Votes: 222,615 | Gross: $153.95M

22. Pretty Woman (1990)

R | 119 min | Comedy, Romance

51 Metascore

A man in a legal but hurtful business needs an escort for some social events, and hires a beautiful prostitute he meets... only to fall in love.

Director: Garry Marshall | Stars: Richard Gere, Julia Roberts, Jason Alexander, Laura San Giacomo

Votes: 261,160 | Gross: $178.41M

23. Pleasantville (1998)

PG-13 | 124 min | Comedy, Drama, Fantasy

71 Metascore

Two 1990s teenage siblings find themselves in a 1950s sitcom, where their influence begins to profoundly change that complacent world.

Director: Gary Ross | Stars: Tobey Maguire, Jeff Daniels, Joan Allen, Reese Witherspoon

Votes: 114,702 | Gross: $40.57M



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