

11/12/1998
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
as Max Fischer

Bill Murray
as Herman Blume

Olivia Williams
as Rosemary Cross

Seymour Cassel
as Bert Fischer

Brian Cox
as Dr. Nelson Guggenheim

Mason Gamble
as Dirk Calloway

Sara Tanaka
as Margaret Yang

Stephen McCole
as Magnus Buchan

Luke Wilson
as Dr. Peter Flynn

Dipak Pallana
as Mr. Adams

Andrew Wilson
as Coach Beck

Marietta Marich
as Mrs. Guggenheim

Ronnie McCawley
as Ronny Blume

Keith McCawley
as Donny Blume

Hae Joon Lee
as Alex

Adebayo Asabi
as Mr. Obiamiwe

Connie Nielsen
as Mrs. Calloway

Al Fielder
as Ernie

Colin Platt
as Boy Portraying Frank Serpico

George Farish
as O'Reilly

Francis Fernandez
as Burnum

McCauley Penderdast
as Fields

Eric Weems
as Willie

Dalton Tomlin
as Wrestler

Wallace Wolodarsky
as Referee

Kim Terry
as Mrs. Blume

Ella Pryor
as Woman Back Stage

Paul Schiff
as Waiter

Antoni Scarano
as Small Boy Artist

Brian Tenenbaum
as Contractor

Thayer McClanahan
as School Reporter

Patricia Winkler
as Mrs. Whitney

Manning Mott
as Mr. Holstead

J.J. Stonebraker
as Woody

Donny Caicedo
as 40 Ounce

Ali Ktiri
as Benjamin

Michael Maggart
as Concierge

Robbie Lee
as Isaac

Morgan Redmond
as Bellman

Ed Geldart
as Security Guard

J.J. Killalea
as Tommy Stalling

William Lau
as Mr. Yang

Lucille Sadikin
as Mrs. Yang

Steve Eckelman
as Tennis Pro

Eric Chase Anderson
as Architect

Danny Fine
as Coach Fritz

Kyle Ryan Urquhart
as Regis

Kumar Pallana
as Mr. LittleJeans

Stephen Dignan
as Reuben

Alexis Bledel
as Student (uncredited)

Brandon Trost
as Vietnamese Soldier with Rocket Launcher (uncredited)

Jason Trost
as Party Kid (uncredited)

David Moritz
as Dynamite Salesman
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