movies before the 21st century
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- DirectorGlenn Gordon CaronStarsJennifer AnistonJay MohrKevin BaconA 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.
- DirectorRob ReinerStarsBilly CrystalMeg RyanCarrie FisherHarry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.
- DirectorLuis MandokiStarsKevin CostnerRobin WrightPaul NewmanA woman discovers a tragic love letter in a bottle on a beach, and is determined to track down its author.
- DirectorRoger KumbleStarsSarah Michelle GellarRyan PhillippeReese WitherspoonTwo vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.
- DirectorReginald HudlinStarsEddie MurphyRobin GivensHalle BerryA 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.
- DirectorJohn HughesStarsEmilio EstevezJudd NelsonMolly RingwaldFive high school students meet in Saturday detention and discover how they have a great deal more in common than they thought.
- DirectorBlair TreuStarsKatherine HeiglDanielle HarrisDonnie JeffcoatA younger sister wishes to switch places with her popular older sister and the two bickering siblings awaken to find the wish has come true.
- DirectorNancy MeyersStarsLindsay LohanDennis QuaidNatasha RichardsonIdentical 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.
- DirectorGil JungerStarsHeath LedgerJulia StilesJoseph Gordon-LevittA 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.
- DirectorJohn SchultzStarsMelissa Joan HartAdrian GrenierStephen CollinsNicole 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?
- DirectorJohn HughesStarsMolly RingwaldAnthony Michael HallJustin HenryA girl's "sweet" sixteenth birthday is anything but special: her family forgets about it, and she suffers from every embarrassment possible.
- DirectorBarry SonnenfeldStarsAnjelica HustonRaul JuliaChristopher LloydCon artists plan to fleece an eccentric family using an accomplice who claims to be their long-lost uncle.
- DirectorCameron CroweStarsJohn CusackIone SkyeJohn MahoneyA noble underachiever and a beautiful valedictorian fall in love the summer before she goes off to college.
- DirectorJames TobackStarsMolly RingwaldRobert Downey Jr.Dennis HopperA womanizer meets his match when he falls for a woman in debt to the mafia.
- DirectorTaylor HackfordStarsRichard GereDebra WingerDavid KeithA 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.
- DirectorJoe JohnstonStarsRobin WilliamsKirsten DunstBonnie HuntWhen 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.
- DirectorNora EphronStarsTom HanksMeg RyanGreg KinnearBook 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.
- DirectorRichard LinklaterStarsEthan HawkeJulie DelpyAndrea EckertA 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.
- DirectorNora EphronStarsTom HanksMeg RyanRoss MalingerA recently widowed man's son calls a radio talk-show in an attempt to find his father a partner.
- DirectorRoger MichellStarsHugh GrantJulia RobertsRichard McCabeA 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.
- DirectorFrancis Ford CoppolaStarsMarlon BrandoAl PacinoJames CaanThe aging patriarch of an organized crime dynasty transfers control of his clandestine empire to his reluctant son.
- DirectorAmy HeckerlingStarsAlicia SilverstoneStacey DashBrittany MurphyShallow, 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.