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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