Never Been Kissed is a 1999 comedy film

Comedy film

Comedy film is a genre of film in which the main emphasis is on humour. They are designed to elicit laughter from the audience. Comedies are mostly light-hearted dramas and are made to amuse and entertain the audiences...

 directed by Raja Gosnell

Raja Gosnell

Raja Raymond Gosnell is an American film director and editor best known for directing films like Never Been Kissed, Big Momma's House, Scooby-Doo, Scooby-Doo 2: Monsters Unleashed, Beverly Hills Chihuahua, and most recently, The Smurfs...

 and starring Drew Barrymore

Drew Barrymore

Drew Blyth Barrymore is an American actress, film director, screenwriter, producer and model. She is a member of the Barrymore family of American actors and granddaughter of John Barrymore. She first appeared in an advertisement when she was 11 months old. Barrymore made her film debut in Altered...

, David Arquette

David Arquette

David Arquette is an American actor, film director, producer, screenwriter, fashion designer, and occasional professional wrestler. A member of the Arquette acting family, he first became known during the mid 1990s after starring in several Hollywood films, such as the Scream series, Wild Bill and...

, Michael Vartan

Michael Vartan

Michael S. Vartan is a French-American film and television actor. He is probably best known for the role of Michael Vaughn on the American television action drama Alias...

, Molly Shannon

Molly Shannon

Molly Helen Shannon is an American comic actress best known for her work as a cast member on Saturday Night Live from 1995–2001 and for starring in the films Superstar and Year of the Dog. More recently, she starred in NBC's Kath & Kim from 2008–2009 and on the TBS animated series Neighbors from...

, Leelee Sobieski

Leelee Sobieski

Liliane Rudabet Gloria Elsveta Sobieski , known professionally as Leelee Sobieski, is an American actress. Sobieski achieved recognition in her mid-teens for her performance in the 1998 film Deep Impact...

, John C. Reilly

John C. Reilly

John Christopher Reilly, Jr. is an American film and theater actor, singer, and comedian. Debuting in Casualties of War in 1989, he is one of several actors whose careers were launched by Brian De Palma. To date, he has appeared in more than fifty films, including three separate films in 2002...

, Jessica Alba

Jessica Alba

Jessica Marie Alba is an American television and film actress. She began her television and movie appearances at age 13 in Camp Nowhere and The Secret World of Alex Mack . Alba rose to prominence as the lead actress in the television series Dark Angel...

, Marley Shelton

Marley Shelton

Marley Eve Shelton is an American film and television actress.Shelton began her acting career in her late teens, and appeared in several 1990s' television movies and shows. She made her film debut in the critically acclaimed drama Grand Canyon , and was cast in the films The Sandlot , Nixon , and...

, James Franco

James Franco

James Edward Franco is an American actor, film director, producer, screenwriter, author, painter, performance artist and instructor at New York University. He left college in order to pursue acting and started off his career by making guest appearances on television series in the 1990s...

 (in his film debut), Giuseppe Andrews

Giuseppe Andrews

Giuseppe Andrews is an American film actor, writer, and director known for his roles as Lex in the 1999 film Detroit Rock City, a bizarre sheriff's deputy in Cabin Fever , a small role in Never Been Kissed , as well as appearances in The Smashing Pumpkins videos "1979" and "Perfect".Andrews has...

, Jeremy Jordan and Garry Marshall

Garry Marshall

Garry Kent Marshall is an American actor, director, writer and producer. His notable credits include creating Happy Days and The Odd Couple and directing Nothing In Common, Pretty Woman, Runaway Bride, Valentine's Day, and The Princess Diaries.-Early life:Marshall was born in the New York City...

. Never Been Kissed was produced by 20th Century Fox

20th Century Fox

Twentieth Century Fox Film Corporation — also known as 20th Century Fox, or simply 20th or Fox — is one of the six major American film studios...

 and Drew Barrymore's production company, Flower Films

Flower Films

Flower Films is a commercial film production company founded by Drew Barrymore in 1995 with Nancy Juvonen. Flower Films has produced ten movies and several television shows to date...

.
Josie Geller (Drew Barrymore

Drew Barrymore

Drew Blyth Barrymore is an American actress, film director, screenwriter, producer and model. She is a member of the Barrymore family of American actors and granddaughter of John Barrymore. She first appeared in an advertisement when she was 11 months old. Barrymore made her film debut in Altered...

) is a highly intelligent, but socially inept, copy editor for the Chicago Sun-Times

Chicago Sun-Times

The Chicago Sun-Times is an American daily newspaper published in Chicago, Illinois. It is the flagship paper of the Sun-Times Media Group.-History:The Chicago Sun-Times is the oldest continuously published daily newspaper in the city...

who has never had a real relationship. One day during a staff meeting, the tyrannical editor-in-chief, Rigfort (Garry Marshall

Garry Marshall

Garry Kent Marshall is an American actor, director, writer and producer. His notable credits include creating Happy Days and The Odd Couple and directing Nothing In Common, Pretty Woman, Runaway Bride, Valentine's Day, and The Princess Diaries.-Early life:Marshall was born in the New York City...

) assigns her to report undercover at a high school to help parents become more aware of their children's lives.

Josie tells her brother Rob (David Arquette

David Arquette

David Arquette is an American actor, film director, producer, screenwriter, fashion designer, and occasional professional wrestler. A member of the Arquette acting family, he first became known during the mid 1990s after starring in several Hollywood films, such as the Scream series, Wild Bill and...

) about the assignment, and he reminds her that during high school she was a misfit labelled "Josie Grossie", a nickname

Nickname

A nickname is "a usually familiar or humorous but sometimes pointed or cruel name given to a person or place, as a supposedly appropriate replacement for or addition to the proper name.", or a name similar in origin and pronunciation from the original name....

 which continues to haunt her.

Her first day at South Glen South High School is miserable.