Kevin Kline

Character: Howard Brackett

Joan Cusack

Character: Emily Montgomery

Tom Selleck

Character: Peter Malloy

Matt Dillon

Character: Cameron Drake

Debbie Reynolds

Character: Berniece Brackett

Wilford Brimley

Character: Frank Brackett

Bob Newhart

Character: Tom Halliwell

Gregory Jbara

Character: Walter Brackett

Shalom Harlow

Character: Sonya

Shawn Hatosy

Character: Jack

Zak Orth

Character: Mike

Lauren Ambrose

Character: Vicky

Deborah Rush

Character: Ava Blazer

June Squibb

Character: Cousin Gretchen

Alice Drummond

Character: Aunt Susan

Alexandra Holden

Character: Meredith

Selma Blair

Character: Cousin Linda

Bill Camp

Character: Bachelor Party Guest

Lauren Ward

Character: Student

J. Smith-Cameron

Character: Trina Paxton

Ernie Sabella

Character: Aldo Hooper

Dan Hedaya

Character: Military Attorney

Becky Ann Baker

Character: Darlene

Lewis J. Stadlen

Character: Ed Kenrow

Kate McGregor-Stewart

Character: Aunt Becky

Debra Monk

Character: Mrs. Lester

John Cunningham

Character: 'Be a Man' Tape Instructor (voice)

Gus Rogerson

Character: Danny

Joseph Maher

Character: Father Tim

William Parry

Character: Fred Mooney

William Duell

Character: Emmett Wilson

Richard Woods

Character: Reverend Morgan

Kevin Chamberlin

Character: Carl Mickley

Wally Dunn

Character: Cousin Lenny

Larry Clarke

Character: Cousin Ernie

Mary Diveny

Character: Cousin Ellen

Anne Russell

Character: Aunt Marge

Patrick Garner

Character: Stan Forrest

Adam LeFevre

Character: Bachelor Party Guest

Scott Robertson

Character: Bachelor Party Guest

John Christopher Jones

Character: Bachelor Party Guest

MacIntyre Dixon

Character: Bachelor Party Guest

Joanna Wolff

Character: Jennifer the Flower Girl

Chris L. McKenna

Character: Locker Room Guy

Mark Ballou

Character: Locker Room Guy

Charlie Newmark

Character: Locker Room Guy

Andrew Levitas

Character: Locker Room Guy

Jon Hershfield

Character: Locker Room Guy

D.J. Dierker

Character: Locker Room Guy

Seth Ullian

Character: Locker Room Guy

Gregory Siff

Character: Locker Room Guy

Ryan Janis

Character: Locker Room Guy

Jane Hoffman

Character: Mrs. Baxter

Bill Hoag

Character: Bartender

Daniel B. Canton

Character: Cameraman

Patricia Guinan

Character: Billy's Mom

Nesbitt Blaisdell

Character: Billy's Dad

Samantha Buck

Character: Classroom Student

Lauren Fox

Character: Classroom Student

Lizzy Mahon

Character: Classroom Student

Simone Marean

Character: Classroom Student

Michael McGruther

Character: Classroom Student

Niki Roma

Character: Classroom Student

Jacqueline Manning

Character: Classroom Student

Patrick Mylod

Character: Classroom Student

Virginia Williams

Character: Classroom Student

Jill Horner

Character: Student

Julie Entwisle

Character: Student

Clare Kramer

Character: Student

Miranda Kent

Character: Student

Tara Carnes

Character: Student

Arden Myrin

Character: Student

Ian Sherwood

Character: Student

Kevin Keating

Character: Student

Kathy Lyn Cavanaugh

Character: Student

Jo-Jo Lowe

Character: Awards Event Model

Lisa Emery

Character: Classroom Reporter

Gary DeWitt Marshall

Character: Classroom Reporter

Marla Sucharetza

Character: School Reporter

Ronald Rand

Character: School Reporter

Ross de Marco

Character: School Reporter

Joanne DiMauro

Character: School Reporter

Tony Jones

Character: School Reporter

Grace DeSena

Character: School Reporter

Bruce Bennetts

Character: School Reporter

Tracy Appleton

Character: School Reporter

Jim Taylor McNickle

Character: School Reporter

Laura Caulfield

Character: School Reporter

Mimi Stuart

Character: School Reporter

Dinah Gravel

Character: School Reporter

Peter Barmonde

Character: Wedding Photographer

Glenn Close

Character: Glenn Close

Whoopi Goldberg

Character: Whoopi Goldberg

Jay Leno

Character: Jay Leno

Jovanna Vitiello

Character: Reporter (uncredited)