When a beautiful first-grade teacher arrives at a prep school, she soon attracts the attention of an ambitious teenager named Max, who quickly falls in love with her. Max turns to the father of two of his schoolmates for advice on how to woo the teacher. However, the situation soon gets complicated when Max's new friend becomes involved with her, setting the two pals against one another in a war for her attention.
Jason Schwartzman
Max Fischer
Bill Murray
Herman Blume
Olivia Williams
Rosemary Cross
Seymour Cassel
Bert Fischer
Brian Cox
Dr. Nelson Guggenheim
Mason Gamble
Dirk Calloway
Sara Tanaka
Margaret Yang
Stephen McCole
Magnus Buchan
Luke Wilson
Dr. Peter Flynn
Dipak Pallana
Mr. Adams
Andrew Wilson
Coach Beck
Marietta Marich
Mrs. Guggenheim
Ronnie McCawley
Ronny Blume
Keith McCawley
Donny Blume
Hae Joon Lee
Alex
Adebayo Asabi
Mr. Obiamiwe
Connie Nielsen
Mrs. Calloway
Al Fielder
Ernie
Colin Platt
Boy Portraying Frank Serpico
George Farish
O'Reilly
Francis Fernandez
Burnum
McCauley Penderdast
Fields
Eric Weems
Willie
Dalton Tomlin
Wrestler
Kim Terry
Mrs. Blume
Ella Pryor
Woman Back Stage
Antoni Scarano
Small Boy Artist
Brian Tenenbaum
Contractor
Thayer McClanahan
School Reporter
Patricia Winkler
Mrs. Whitney
Manning Mott
Mr. Holstead
J.J. Stonebraker
Woody
Donny Caicedo
40 Ounce
Ali Ktiri
Benjamin
Michael Maggart
Concierge
Robbie Lee
Isaac
Morgan Redmond
Bellman
Ed Geldart
Security Guard
J.J. Killalea
Tommy Stalling
William Lau
Mr. Yang
Lucille Sadikin
Mrs. Yang
Steve Eckelman
Tennis Pro
Eric Chase Anderson
Architect
Danny Fine
Coach Fritz
Kyle Ryan Urquhart
Regis
Kumar Pallana
Mr. LittleJeans
Stephen Dignan
Reuben
Alexis Bledel
Student (uncredited)
Jason Trost
Party Kid (uncredited)
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