Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.
Directed by Raja Gosnell
chicago, illinois
high school
newspaper
journalist
entrapment
undercover
nerd
kiss
romcom
love
prank
prom
reporter
humiliation
editor
lighthearted
Rank
#92 in 1999·#6406 overall
Trailer
IMDB
N/A
Where to Watch
Cast
Drew Barrymore
Josie Geller
David Arquette
Rob Geller
Molly Shannon
Anita
Michael Vartan
Sam Coulson
Jessica Alba
Kirsten
John C. Reilly
Gus Strauss
James Franco
Jason
Octavia Spencer
Cynthia
Jenny Bicks
Miss Haskell
Garry Marshall
Rigfort
Sean Whalen
Merkin
Cress Williams
George
Crew
Raja Gosnell
Director
Marc Silverstein
Screenplay
Abby Kohn
Screenplay
Jenny Bicks
Writer
David Newman
Original Music Composer
Nancy Juvonen
Producer
Drew Barrymore
Executive Producer
Mary Ramos
Music Supervisor
Mona May
Costume Designer
Gary Archer
Prosthetics
Lori McCoy-Bell
Hairstylist
Anette Haellmigk
Second Unit Director of Photography
Popular Reviews
1685 reviews
Louis Brown
2.7★ · 07/05/25
What in the fuck…
What in the fuck…
2
mo
1.0★ · 06/06/25
this is a fanfic
this is a fanfic
2
angie
6.0★ · 03/12/26
not like the godfather but we could offer you a certain amount of protection
also why the FUCK was bro mad when he found out she was 25😭
not like the godfather but we could offer you a certain amount of protection
also why the FUCK was bro mad when he found out she was 25😭
