Andie (Molly Ringwald) is an outcast at her Chicago high school, hanging out either with her older boss (Annie Potts), who owns the record store where she works, or her quirky classmate Duckie (Jon Cryer), who has a crush on her. When one of the rich and popular kids at school, Blane (Andrew McCarthy), asks Andie out, it seems too good to be true. As Andie starts falling for Blane, she begins to realizes that dating someone from a different social sphere is not easy.
Three strong women — Roberta Martin (Rosie O’Donnell), Samantha Albertson (Demi Moore) and Tina “Teeny” Tercell (Melanie Griffith) — return home to reunite with their childhood friend Chrissy DeWitt Williams (Rita Wilson) and see her through the end of her first pregnancy. The four lifelong friends share their memories of the unforgettable summer of 1970, the summer their innocent younger selves (Christina Ricci, Gaby Hoffmann, Thora Birch, Ashleigh Aston Moore) grew up.
In this adaptation of Jane Austen’s classic novel, pretty socialite Emma Woodhouse (Gwyneth Paltrow) entertains herself by playing matchmaker for those around her. Her latest “project” is Harriet Smith, an unpretentious debutant, while Emma herself receives the attentions of the dashing Frank Churchill (Ewan McGregor). However, Emma’s attempts at matchmaking cause more problems than solutions and may ultimately jeopardize her own chance at love and happiness.
Teenage Cady Heron (Lindsay Lohan) was educated in Africa by her scientist parents. When her family moves to the suburbs of Illinois, Cady finally gets to experience public school and gets a quick primer on the cruel, tacit laws of popularity that divide her fellow students into tightly knit cliques. She unwittingly finds herself in the good graces of an elite group of cool students dubbed “the Plastics,” but Cady soon realizes how her shallow group of new friends earned this nickname.
Nicole (Melissa Joan Hart) and Chase (Adrian Grenier) live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought.
Veronica (Winona Ryder) is part of the most popular clique at her high school, but she disapproves of the other girls’ cruel behavior. When Veronica and her new boyfriend, J.D. (Christian Slater), confront clique leader Heather Chandler (Kim Walker) and accidentally poison her, they make it appear a suicide. Soon Veronica realizes that J.D. is intentionally killing students he does not like. She races to stop J.D. while also clashing with the clique’s new leader, Heather Duke (Shannen Doherty).
Like many New York City gals, Rebecca Bloomwood (Isla Fisher) loves to shop. The trouble is, she shops so much that she is drowning in debt. Rebecca would love to work at the city’s top fashion magazine but, so far, has not been able to get her foot in the door. Then she lands a job as an advice columnist for a financial magazine owned by the same company. Her column becomes an overnight success, but her secret threatens to ruin her love life and career.