Kevin Kline
Howard Brackett

Joan Cusack
Emily Montgomery

Tom Selleck
Peter Malloy

Matt Dillon
Cameron Drake

Debbie Reynolds
Berniece Brackett

Wilford Brimley
Frank Brackett

Bob Newhart
Tom Halliwell

Gregory Jbara
Walter Brackett

Shalom Harlow
Sonya

Shawn Hatosy
Jack

Zak Orth
Mike

Lauren Ambrose
Vicky

Deborah Rush
Ava Blazer

June Squibb
Cousin Gretchen

Alice Drummond
Aunt Susan

Alexandra Holden
Meredith

Selma Blair
Cousin Linda

Bill Camp
Bachelor Party Guest

Lauren Ward
Student

J. Smith-Cameron
Trina Paxton

Ernie Sabella
Aldo Hooper

Dan Hedaya
Military Attorney

Becky Ann Baker
Darlene

Lewis J. Stadlen
Ed Kenrow

Kate McGregor-Stewart
Aunt Becky

Debra Monk
Mrs. Lester

John Cunningham
'Be a Man' Tape Instructor (voice)

Joseph Maher
Father Tim

William Duell
Emmett Wilson

Richard Woods
Reverend Morgan

Kevin Chamberlin
Carl Mickley

Wally Dunn
Cousin Lenny

Larry Clarke
Cousin Ernie

Patrick Garner
Stan Forrest

Adam LeFevre
Bachelor Party Guest

Scott Robertson
Bachelor Party Guest

John Christopher Jones
Bachelor Party Guest

MacIntyre Dixon
Bachelor Party Guest

Chris L. McKenna
Locker Room Guy

Mark Ballou
Locker Room Guy

Charlie Newmark
Locker Room Guy

Andrew Levitas
Locker Room Guy

D.J. Dierker
Locker Room Guy

Gregory Siff
Locker Room Guy

Jane Hoffman
Mrs. Baxter

Bill Hoag
Bartender

Nesbitt Blaisdell
Billy's Dad

Samantha Buck
Classroom Student

Lauren Fox
Classroom Student

Virginia Williams
Classroom Student

Clare Kramer
Student

Arden Myrin
Student

Kevin Keating
Student

Lisa Emery
Classroom Reporter

Marla Sucharetza
School Reporter

Glenn Close
Glenn Close

Whoopi Goldberg
Whoopi Goldberg

Jay Leno
Jay Leno