Old school teen movies (90s/early 00s)
by knwinans22 | created - 16 Dec 2011 | updated - 12 Jan 2012 | Public- Instant Watch Options
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1. 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: 246,052 | Gross: $56.63M
2. Strike! (1998)
PG-13 | 97 min | Comedy
In the 1960s, a group of friends at an all girls school learn that their school is going to be combined with a nearby all boys school. They concoct a plan to save their school while dealing with everyday problems along the way.
Director: Sarah Kernochan | Stars: Kirsten Dunst, Lynn Redgrave, Gaby Hoffmann, Rachael Leigh Cook
Votes: 7,603 | Gross: $0.97M
3. Bring It On (2000)
PG-13 | 98 min | Comedy, Romance, Sport
A champion high school cheerleading squad discovers its previous captain stole all their best routines from an inner-city school and must scramble to compete at this year's championships.
Director: Peyton Reed | Stars: Kirsten Dunst, Eliza Dushku, Jesse Bradford, Gabrielle Union
Votes: 105,815 | Gross: $68.38M
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: 385,602 | Gross: $38.18M
5. She's All That (1999)
PG-13 | 95 min | Comedy, Romance
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: 103,862 | Gross: $63.37M
6. Whatever It Takes (2000)
PG-13 | 94 min | Comedy, Drama, Romance
A modern-day remake of the Cyrano DeBergerac tale.
Director: David Raynr | Stars: Shane West, Marla Sokoloff, Jodi Lyn O'Keefe, Manu Intiraymi
Votes: 12,004 | Gross: $8.74M
7. Teaching Mrs. Tingle (1999)
PG-13 | 96 min | Comedy, Thriller
The story of a girl who is willing to do anything to become Valedictorian, even if it means murdering the teacher that stands in her way.
Director: Kevin Williamson | Stars: Helen Mirren, Marisa Coughlan, Katie Holmes, Jeffrey Tambor
Votes: 21,720 | Gross: $8.95M
8. 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: 21,300 | Gross: $17.85M
9. 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: 97,591 | Gross: $55.47M
10. American Pie (1999)
R | 95 min | Comedy
Four teenage boys enter a pact to lose their virginity by prom night.
Directors: Paul Weitz, Chris Weitz | Stars: Jason Biggs, Chris Klein, Thomas Ian Nicholas, Jennifer Coolidge
Votes: 433,965 | Gross: $102.56M
11. Jawbreaker (1999)
R | 86 min | Comedy, Crime, Thriller
Three of the most popular girls at Reagan High accidentally kill the prom queen with a jawbreaker when a kidnapping goes horribly wrong.
Director: Darren Stein | Stars: Rose McGowan, Rebecca Gayheart, Julie Benz, Alexandra Adi
Votes: 28,957 | Gross: $3.07M
12. Dude, Where's My Car? (2000)
PG-13 | 83 min | Comedy, Mystery, Sci-Fi
Two potheads wake up after a night of partying and cannot remember where they parked their car.
Director: Danny Leiner | Stars: Ashton Kutcher, Seann William Scott, Jennifer Garner, Marla Sokoloff
Votes: 145,855 | Gross: $46.73M
13.
The Wonderful World of Disney (1997–2023)
Episode:
Life-Size
(2000)
TV-G | 101 min | Adventure, Comedy, Drama
A widower's daughter accidentally brings her doll to life while trying to cast a spell to resurrect her mother.
Director: Mark Rosman | Stars: Lindsay Lohan, Jere Burns, Anne Marie DeLuise, Garwin Sanford
Votes: 8,657
14. Get Over It (2001)
PG-13 | 87 min | Comedy, Romance
A high school senior's girlfriend breaks up with him. His friends try to make him think of something else. His friend's sister Kelly helps him with the school musical. Spending time with Kelly has an effect.
Director: Tommy O'Haver | Stars: Kirsten Dunst, Ben Foster, Melissa Sagemiller, Sisqó
Votes: 20,030 | Gross: $11.58M
15. Romy and Michele's High School Reunion (1997)
R | 92 min | Comedy
Two dim-witted, inseparable friends hit the road for their ten-year high school reunion and concoct an elaborate lie about their lives in order to impress their classmates.
Director: David Mirkin | Stars: Mira Sorvino, Lisa Kudrow, Janeane Garofalo, Alan Cumming
Votes: 53,095 | Gross: $29.21M
16. Au Pair (1999 TV Movie)
96 min | Comedy, Family, Romance
A young MBA mistakenly takes the job of looking after a rich executive's spoiled children.
Director: Mark Griffiths | Stars: Gregory Harrison, Heidi Lenhart, Jane Sibbett, Katie Volding
Votes: 2,162
17. The Rage: Carrie 2 (1999)
R | 104 min | Drama, Horror, Sci-Fi
A horrible massacre strikes up after an outcast teenage girl is taunted by a group of high school jocks, all of them unaware of her cutthroat telekinetic powers.
Directors: Katt Shea, Robert Mandel | Stars: Emily Bergl, Jason London, Dylan Bruno, J. Smith-Cameron
Votes: 17,893 | Gross: $17.76M
18. Sugar & Spice (2001)
PG-13 | 81 min | Comedy, Crime
A popular high-school cheerleader becomes pregnant by the star quarterback and turns to crime to support her desired lifestyle.
Director: Francine McDougall | Stars: Marla Sokoloff, Marley Shelton, Melissa George, Mena Suvari
Votes: 15,334 | Gross: $13.28M
19. Bio-Dome (1996)
PG-13 | 88 min | Comedy
Moronic best friends get themselves locked inside the Bio-Dome, a science experiment, along with a group of environmental scientists for one year.
Director: Jason Bloom | Stars: Pauly Shore, Stephen Baldwin, William Atherton, Denise Dowse
Votes: 29,752 | Gross: $26.76M
20. Drop Dead Fred (1991)
PG-13 | 103 min | Comedy, Drama, Fantasy
A young woman finds her already unstable life rocked by the presence of a rambunctious imaginary friend from childhood.
Director: Ate de Jong | Stars: Phoebe Cates, Rik Mayall, Marsha Mason, Tim Matheson
Votes: 31,441 | Gross: $43.88M
21. Drop Dead Gorgeous (1999)
PG-13 | 97 min | Comedy, Romance, Thriller
A small-town beauty pageant turns deadly as it becomes clear that someone will go to any lengths to win.
Director: Michael Patrick Jann | Stars: Kirsten Dunst, Denise Richards, Ellen Barkin, Allison Janney
Votes: 40,832 | Gross: $10.56M
22. Dick (1999)
PG-13 | 94 min | Comedy
After wandering off during a White House tour, two high school girls inadvertently become Richard Nixon's top secret advisers at the height of the Watergate scandal.
Director: Andrew Fleming | Stars: Kirsten Dunst, Michelle Williams, Dan Hedaya, Will Ferrell
Votes: 21,372 | Gross: $6.24M
23. A Walk to Remember (2002)
PG | 101 min | Drama, Romance
Two North Carolina teens, Landon Carter and Jamie Sullivan, are thrown together after Landon gets into trouble and is sentenced to perform community service.
Director: Adam Shankman | Stars: Mandy Moore, Shane West, Peter Coyote, Daryl Hannah
Votes: 221,422 | Gross: $41.28M
24. Loser (2000)
PG-13 | 98 min | Comedy, Romance
A college student, branded a loser by his roommates and booted from the dorm, falls in love with a coed who has eyes for their condescending professor.
Director: Amy Heckerling | Stars: Jason Biggs, Mena Suvari, Zak Orth, Thomas Sadoski
Votes: 30,361 | Gross: $15.62M
25. 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: 53,992 | Gross: $25.34M
26. Josie and the Pussycats (2001)
PG-13 | 98 min | Comedy, Music
A girl group find themselves in the middle of a conspiracy to deliver subliminal messages through popular music.
Directors: Harry Elfont, Deborah Kaplan | Stars: Rachael Leigh Cook, Tara Reid, Rosario Dawson, Alan Cumming
Votes: 24,937 | Gross: $14.25M
27. The Princess Diaries (2001)
G | 115 min | Comedy, Family, Romance
Mia Thermopolis has just found out that she is the heir apparent to the throne of Genovia. With her friends Lilly and Michael Moscovitz in tow, she tries to navigate through the rest of her sixteenth year.
Director: Garry Marshall | Stars: Julie Andrews, Anne Hathaway, Hector Elizondo, Heather Matarazzo
Votes: 163,693 | Gross: $108.25M
28. Coyote Ugly (2000)
PG-13 | 100 min | Comedy, Drama, Music
Aspiring songwriter Violet Sanford, after getting a job at a women-run NYC bar that teases its male patrons, comes out of her shell.
Director: David McNally | Stars: Piper Perabo, Adam Garcia, John Goodman, Maria Bello
Votes: 120,960 | Gross: $60.79M
29. 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: 248,353 | Gross: $96.52M
30. The Baby-Sitters Club (1995)
PG | 94 min | Comedy, Drama, Family
Seven junior-high-school girls organize a daycare camp for children while at the same time experiencing classic adolescent growing pains.
Director: Melanie Mayron | Stars: Schuyler Fisk, Bre Blair, Rachael Leigh Cook, Larisa Oleynik
Votes: 6,211 | Gross: $9.69M
31. Now and Then (1995)
PG-13 | 102 min | Comedy, Drama, Romance
Four 12-year-old girls grow up together during an eventful small-town summer in 1970.
Director: Lesli Linka Glatter | Stars: Christina Ricci, Demi Moore, Rosie O'Donnell, Thora Birch
Votes: 32,441 | Gross: $27.40M
32. Miss Congeniality (2000)
PG-13 | 109 min | Action, Comedy, Crime
An F.B.I. Agent must go undercover in the Miss United States beauty pageant to prevent a group from bombing the event.
Director: Donald Petrie | Stars: Sandra Bullock, Michael Caine, Benjamin Bratt, Candice Bergen
Votes: 230,421 | Gross: $106.81M
33. Save the Last Dance (2001)
PG-13 | 112 min | Drama, Music, Romance
A white midwestern girl moves to Chicago, where her new boyfriend is a black teen from the South Side with a rough, semi-criminal past.
Director: Thomas Carter | Stars: Julia Stiles, Sean Patrick Thomas, Kerry Washington, Fredro Starr
Votes: 65,996 | Gross: $91.06M
34. Pleasantville (1998)
PG-13 | 124 min | Comedy, Drama, Fantasy
Two 1990s teenage siblings find themselves transported to a 1950s sitcom where their influence begins to profoundly change that colorless, complacent world.
Director: Gary Ross | Stars: Tobey Maguire, Jeff Daniels, Joan Allen, William H. Macy
Votes: 136,353 | Gross: $40.57M
35. Zoolander (2001)
PG-13 | 90 min | Comedy
At the end of his career, a clueless fashion model is brainwashed to kill the Prime Minister of Malaysia.
Director: Ben Stiller | Stars: Ben Stiller, Owen Wilson, Christine Taylor, Will Ferrell
Votes: 292,007 | Gross: $45.17M
36. Spice World (1997)
PG | 93 min | Comedy, Family, Music
World-famous pop group the Spice Girls zip around London in their luxurious double-decker tour bus having various adventures and performing for their fans.
Director: Bob Spiers | Stars: Mel B, Emma Bunton, Melanie C, Geri Horner
Votes: 37,852 | Gross: $29.34M
37. Good Burger (1997)
PG | 95 min | Comedy, Family
A dim-witted teenager and his new coworker try to save the old burger joint they work for from failing after the opening of a brand new burger restaurant across the street, which's planning to put them out of business.
Director: Brian Robbins | Stars: Kel Mitchell, Kenan Thompson, Sinbad, Abe Vigoda
Votes: 33,679 | Gross: $23.69M
38. House Arrest (1996)
PG | 108 min | Comedy, Family
Desperate to keep their various parents from getting divorced, a group of teenagers kidnaps them and holds them prisoner in a basement to force them to reconcile.
Director: Harry Winer | Stars: Jamie Lee Curtis, Kevin Pollak, Kyle Howard, Herbert Russell
Votes: 9,257 | Gross: $6.97M
39.
The Wonderful World of Disney (1997–2023)
Episode:
Model Behavior
(2000)
TV-G | 85 min | Adventure, Comedy, Drama
Two teenage girls, one an ordinary high school girl and the other a top teen model, who meet and switch places.
Director: Mark Rosman | Stars: Maggie Lawson, Jim Abele, Daniel Clark, Karen Hines
Votes: 2,815
40. Ever After: A Cinderella Story (1998)
PG-13 | 121 min | Drama, Romance
The Brothers Grimm arrive at the home of a wealthy Grande Dame who speaks of the many legends surrounding the fable of the cinder girl before telling the "true" story of her ancestor.
Director: Andy Tennant | Stars: Drew Barrymore, Anjelica Huston, Dougray Scott, Patrick Godfrey
Votes: 81,760 | Gross: $65.71M
41. Harriet the Spy (1996)
PG | 100 min | Comedy, Drama, Family
Harriet M. Welsch is a spy. But when her friends find her secret notebook, the tables are turned on her. Can she win them back and still keep on going with the spy business?
Director: Bronwen Hughes | Stars: Michelle Trachtenberg, Rosie O'Donnell, Gregory Smith, Vanessa Chester
Votes: 11,065 | Gross: $26.54M
42. The Flintstones (1994)
PG | 91 min | Comedy, Family, Fantasy
In a parallel modern-day Stone Age world, a working-class family, the Flintstones, are set up for an executive job. But they learn that money can't buy happiness.
Director: Brian Levant | Stars: John Goodman, Rick Moranis, Rosie O'Donnell, Halle Berry
Votes: 86,568 | Gross: $130.51M
43. The Sandlot (1993)
PG | 101 min | Comedy, Drama, Family
In the summer of 1962, a new kid in town is taken under the wing of a young baseball prodigy and his rowdy team, resulting in many adventures.
Director: David Mickey Evans | Stars: Tom Guiry, Mike Vitar, Art LaFleur, Patrick Renna
Votes: 102,442 | Gross: $32.42M
44. Coneheads (1993)
PG | 88 min | Comedy, Sci-Fi
Aliens with conical crania crash-land on Earth.
Director: Steve Barron | Stars: Dan Aykroyd, Jane Curtin, Robert Knott, Jonathan Penner
Votes: 58,012 | Gross: $21.27M
45. George of the Jungle (1997)
PG | 92 min | Action, Adventure, Comedy
A man raised in the jungle by apes falls in love with a wealthy American heiress.
Director: Sam Weisman | Stars: Brendan Fraser, Leslie Mann, Thomas Haden Church, Richard Roundtree
Votes: 84,410 | Gross: $105.26M
46. Jungle 2 Jungle (1997)
PG | 105 min | Comedy, Family
A man learns he has a thirteen-year-old son who was raised in the jungle and brings the boy to New York City, turning his life upside down in the process.
Director: John Pasquin | Stars: Tim Allen, Martin Short, JoBeth Williams, Lolita Davidovich
Votes: 25,865 | Gross: $59.93M
47. Mrs. Doubtfire (1993)
PG-13 | 125 min | Comedy, Drama
After a bitter divorce, an actor disguises himself as a female housekeeper to spend time with his children held in custody by his former wife.
Director: Chris Columbus | Stars: Robin Williams, Sally Field, Pierce Brosnan, Harvey Fierstein
Votes: 291,124 | Gross: $219.20M
48. Matilda (1996)
PG | 102 min | Comedy, Family, Fantasy
A girl gifted with a keen intellect and psychic powers uses both to get even with her callous family and free her kindly schoolteacher from the tyrannical grip of a sadistic headmistress.
Director: Danny DeVito | Stars: Danny DeVito, Rhea Perlman, Mara Wilson, Embeth Davidtz
Votes: 174,703 | Gross: $33.08M
49.
The Wonderful World of Disney (1997–2023)
Episode:
My Date with the President's Daughter
(1998)
TV-G | 90 min | Adventure, Comedy, Drama
A teenager unwittingly falls for the American President's daughter, and the pair soon find themselves off on a wild adventure.
Director: Alex Zamm | Stars: Dabney Coleman, Will Friedle, Elisabeth Harnois, Mimi Kuzyk
Votes: 4,472
50. Blast from the Past (1999)
PG-13 | 112 min | Comedy, Drama, Romance
A naive man comes out into the world after spending 35 years in a nuclear fallout shelter.
Director: Hugh Wilson | Stars: Brendan Fraser, Alicia Silverstone, Christopher Walken, Sissy Spacek
Votes: 71,759 | Gross: $26.49M
51. 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: 8,422
52. Zenon: Girl of the 21st Century (1999 TV Movie)
TV-G | 97 min | Adventure, Comedy, Family
An inquisitive teenager pries into suspected dodgy dealings on her space station home - and ends up being sent down to Earth.
Director: Kenneth Johnson | Stars: Kirsten Storms, Raven-Symoné, Bob Bancroft, Stuart Pankin
Votes: 8,382
53. Smart House (1999 TV Movie)
TV-G | 82 min | Comedy, Drama, Family
A teenager wins a fully-automated dream house in a competition, but soon the computer controlling it begins to take over and everything gets out of control. Then teenage Ben must calm the computer named PAT.
Director: LeVar Burton | Stars: Katey Sagal, Ryan Merriman, Katie Volding, Kevin Kilner
Votes: 8,287
54. Get a Clue (2002 TV Movie)
TV-G | 83 min | Comedy, Crime, Family
A wealthy student with too much fashion sense, her equally rich friends, and her rival/superior from the school paper work together to solve the case when their teacher goes missing.
Director: Maggie Greenwald | Stars: Lindsay Lohan, Bug Hall, Ian Gomez, Brenda Song
Votes: 7,282
55. Double Teamed (2002 TV Movie)
TV-G | 93 min | Biography, Drama, Family
Two sisters become world-famous basketball players.
Director: Duwayne Dunham | Stars: Poppi Monroe, Annie McElwain, Teal Redmann, Nick Searcy
Votes: 3,998
56. Quints (2000 TV Movie)
TV-G | 83 min | Comedy, Drama, Family
14-year-old Jamie goes to desperate lengths to get attention when her mother gives birth to quintuplets.
Director: Bill Corcoran | Stars: Kimberly J. Brown, Daniel Roebuck, Elizabeth Morehead, Shadia Simmons
Votes: 2,705
57. The Color of Friendship (2000 TV Movie)
TV-G | 87 min | Biography, Drama, Family
A white South African girl finds herself in a difficult situation when she is sent to spend a term with a Black family in America.
Director: Kevin Hooks | Stars: Lindsey Haun, Shadia Simmons, Carl Lumbly, Penny Johnson Jerald
Votes: 4,312
58. Tru Confessions (2002 TV Movie)
TV-G | 112 min | Comedy, Drama, Family
Trudy Walker hated her life. She thought it was totally messed up until she found out about a contest that could change everything..
Director: Paul Hoen | Stars: Clara Bryant, Shia LaBeouf, Mare Winningham, William Francis McGuire
Votes: 3,391
59. 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: 377,074 | Gross: $100.48M
60. Crossroads (I) (2002)
PG-13 | 93 min | Comedy, Drama, Romance
Three childhood friends embark on a cross-country adventure to pursue dreams they once put aside, taking risks that are sure to change their lives forever.
Director: Tamra Davis | Stars: Britney Spears, Anson Mount, Zoe Saldana, Taryn Manning
Votes: 44,142 | Gross: $37.19M
61. Cadet Kelly (2002 TV Movie)
TV-G | 101 min | Comedy, Drama, Family
A fashion-conscious youngster is horrified when she is forced to move to military school.
Director: Larry Shaw | Stars: Hilary Duff, Christy Carlson Romano, Gary Cole, Shawn Ashmore
Votes: 15,460
62. Blue Crush (2002)
PG-13 | 104 min | Drama, Romance, Sport
As a hard-core surfer girl prepares for a big competition, she finds herself falling for a football player.
Director: John Stockwell | Stars: Kate Bosworth, Michelle Rodriguez, Matthew Davis, Sanoe Lake
Votes: 32,918 | Gross: $40.39M
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