Cast
- Kevin Kline as Howard Brackett, an English teacher
- Joan Cusack as Emily Montgomery, Howard's fiancee
- Tom Selleck as Peter Malloy, a TV journalist covering Howard's story
- Matt Dillon as Cameron Drake, an ex-student of Howard's and Oscar-winning actor
- Debbie Reynolds as Berniece Brackett, Howard's mother
- Wilford Brimley as Frank Brackett, Howard's father
- Bob Newhart as Tom Halliwell, Howard's school's principal
- Shawn Hatosy as Jack, one of Howard's students
- Zak Orth as Mike, one of Howard's students
- Alexandra Holden as Meredith, one of Howard's students
- Lauren Ambrose as Vicky, one of Howard's students
- Shalom Harlow as Sonya, Cameron's supermodel girlfriend
- Gregory Jbara as Walter Brackett, Howard's brother
- Lewis J. Stadlen as Edward Kenrow, one of Howard's colleagues
- Deborah Rush as Ava Blazer, one of Howard's colleagues
- Kevin Chamberlin as Carl Mickley, one of Howard's colleagues
- Kate McGregor-Stewart as Aunt Becky, one of Howard's relatives
- Debra Monk as Mrs. Lester, the town dressmaker
- Ernie Sabella as Aldo Hooper, Howard's hair stylist
- Joseph Maher as Father Tim, one of the town's priests from whom Howard seeks help.
- William Duell as Emmett Wilson, the town mailman
- Alice Drummond as Aunt Susan, one of Howard's relatives
- Selma Blair as Cousin Linda, one of Howard's relatives
- Whoopi Goldberg, Glenn Close, and Jay Leno appear as themselves.
- Dan Hedaya appears as the Military Attorney in "To Serve and Protect"
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