
Plot
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.
Trailer
Cast

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

Wallace Wolodarsky
Referee

Kim Terry
Mrs. Blume

Ella Pryor
Woman Back Stage

Paul Schiff
Waiter

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)

Brandon Trost
Vietnamese Soldier with Rocket Launcher (uncredited)

Jason Trost
Party Kid (uncredited)

David Moritz
Dynamite Salesman