Kevin Kline as Howard Brackett

Joan Cusack as Emily Montgomery

Tom Selleck as Peter Malloy

Matt Dillon as Cameron Drake

Debbie Reynolds as Berniece Brackett

Wilford Brimley as Frank Brackett

Bob Newhart as Tom Halliwell

Gregory Jbara as Walter Brackett

Shalom Harlow as Sonya

Shawn Hatosy as Jack

Zak Orth as Mike

Lauren Ambrose as Vicky

Deborah Rush as Ava Blazer

June Squibb as Cousin Gretchen

Alice Drummond as Aunt Susan

Alexandra Holden as Meredith

Selma Blair as Cousin Linda

Bill Camp as Bachelor Party Guest

Lauren Ward as Student

J. Smith-Cameron as Trina Paxton

Ernie Sabella as Aldo Hooper

Dan Hedaya as Military Attorney

Becky Ann Baker as Darlene

Lewis J. Stadlen as Ed Kenrow

Kate McGregor-Stewart as Aunt Becky

Debra Monk as Mrs. Lester

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

Gus Rogerson as Danny

Joseph Maher as Father Tim

William Parry as Fred Mooney

William Duell as Emmett Wilson

Richard Woods as Reverend Morgan

Kevin Chamberlin as Carl Mickley

Wally Dunn as Cousin Lenny

Larry Clarke as Cousin Ernie

Mary Diveny as Cousin Ellen

Anne Russell as Aunt Marge

Patrick Garner as Stan Forrest

Adam LeFevre as Bachelor Party Guest

Scott Robertson as Bachelor Party Guest

John Christopher Jones as Bachelor Party Guest

MacIntyre Dixon as Bachelor Party Guest

Joanna Wolff as Jennifer the Flower Girl

Chris L. McKenna as Locker Room Guy

Mark Ballou as Locker Room Guy

Charlie Newmark as Locker Room Guy

Andrew Levitas as Locker Room Guy

Jon Hershfield as Locker Room Guy

D.J. Dierker as Locker Room Guy

Seth Ullian as Locker Room Guy

Gregory Siff as Locker Room Guy

Ryan Janis as Locker Room Guy

Jane Hoffman as Mrs. Baxter

Bill Hoag as Bartender

Daniel B. Canton as Cameraman

Patricia Guinan as Billy's Mom

Nesbitt Blaisdell as Billy's Dad

Samantha Buck as Classroom Student

Lauren Fox as Classroom Student

Lizzy Mahon as Classroom Student

Simone Marean as Classroom Student

Michael McGruther as Classroom Student

Niki Roma as Classroom Student

Jacqueline Manning as Classroom Student

Patrick Mylod as Classroom Student

Virginia Williams as Classroom Student

Jill Horner as Student

Julie Entwisle as Student

Clare Kramer as Student

Miranda Kent as Student

Tara Carnes as Student

Arden Myrin as Student

Ian Sherwood as Student

Kevin Keating as Student

Kathy Lyn Cavanaugh as Student

Jo-Jo Lowe as Awards Event Model

Lisa Emery as Classroom Reporter

Gary DeWitt Marshall as Classroom Reporter

Marla Sucharetza as School Reporter

Ronald Rand as School Reporter

Ross de Marco as School Reporter

Joanne DiMauro as School Reporter

Tony Jones as School Reporter

Grace DeSena as School Reporter

Bruce Bennetts as School Reporter

Tracy Appleton as School Reporter

Jim Taylor McNickle as School Reporter

Laura Caulfield as School Reporter

Mimi Stuart as School Reporter

Dinah Gravel as School Reporter

Peter Barmonde as Wedding Photographer

Glenn Close as Glenn Close

Whoopi Goldberg as Whoopi Goldberg

Jay Leno as Jay Leno

Jovanna Vitiello as Reporter (uncredited)