Never Been Kissed

(1999)

107 minutes

Comedy

Directed by Raja Gosnell

Cast:

Drew Barrymore as Josie Geller
Michael Vartan as Sam Coulson
David Arquette as Rob Geller
John C. Reilly as Augustus 'Gus' Strauss
Leelee Sobieski as Aldys
Jeremy Jordan as Guy Perkins
Jordan Ladd as Gibby
Jessica Alba as Kirsten
Marley Shelton as Kristen 
Molly Shannon as Anita
Denny Kirkwood as Billy Prince
Marissa Jaret Winokur as Sheila
Maya McLaughlin as Lara
Giuseppe Andrews as Denominator
Branden Williams as Tommy
James Edward Franco as Jason
Octavia Spencer as Cynthia
Garry Marshall as Wigfort
Sean Whalen as Merkin 
 
Josie Gellar is a 25-year old Chicago Sun Times editor who is determined to become a reporter and gets an opportunity to show her work by going undercover as a high school student. Josie was a big-time nerd in high school and was always getting made fun of, but her funny and popular brother helps her to shine bright. Her teacher, Sam Coulson, finds Josie intelligent and enjoys her company. She is afraid to blow her cover, yet does not want to ruin her career. 

Never Been Kissed trailer