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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) Gus Rogerson Danny Joseph Maher Father Tim William Parry Fred Mooney William Duell Emmett Wilson Richard Woods Reverend Morgan Kevin Chamberlin Carl Mickley Wally Dunn Cousin Lenny Larry Clarke Cousin Ernie Mary Diveny Cousin Ellen Anne Russell Aunt Marge 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 Joanna Wolff Jennifer the Flower Girl Chris L. McKenna Locker Room Guy Mark Ballou Locker Room Guy Charlie Newmark Locker Room Guy Andrew Levitas Locker Room Guy Jon Hershfield Locker Room Guy D.J. Dierker Locker Room Guy Seth Ullian Locker Room Guy Gregory Siff Locker Room Guy Ryan Janis Locker Room Guy Jane Hoffman Mrs. Baxter Bill Hoag Bartender Daniel B. Canton Cameraman Patricia Guinan Billy's Mom Nesbitt Blaisdell Billy's Dad Samantha Buck Classroom Student Lauren Fox Classroom Student Lizzy Mahon Classroom Student Simone Marean Classroom Student Michael McGruther Classroom Student Niki Roma Classroom Student Jacqueline Manning Classroom Student Patrick Mylod Classroom Student Virginia Williams Classroom Student Jill Horner Student Julie Entwisle Student Clare Kramer Student Miranda Kent Student Tara Carnes Student Arden Myrin Student Ian Sherwood Student Kevin Keating Student Kathy Lyn Cavanaugh Student Jo-Jo Lowe Awards Event Model Lisa Emery Classroom Reporter Gary DeWitt Marshall Classroom Reporter Marla Sucharetza School Reporter Ronald Rand School Reporter Ross de Marco School Reporter Joanne DiMauro School Reporter Tony Jones School Reporter Grace DeSena School Reporter Bruce Bennetts School Reporter Tracy Appleton School Reporter Jim Taylor McNickle School Reporter Laura Caulfield School Reporter Mimi Stuart School Reporter Dinah Gravel School Reporter Peter Barmonde Wedding Photographer Glenn Close Glenn Close Whoopi Goldberg Whoopi Goldberg Jay Leno Jay Leno Jovanna Vitiello Reporter (uncredited)