- Keira Knightley - Gwyn
- Paul Kennedy - Sgt. Schmidt
- Stacy Fair - Angels Fan
- Harland Williams - Tucker / Headmistress
- Shawna Waldron - Beryl Andrews
- Duane Martin - Jim
- Lori Hallier - Sally Jeffries
- Lawrence Dane - Rawlings
- Conrad Dunn - Farley
- Katey Sagal - Harriet Magnum
- Aimée Castle - Wendy
- Kerry Duff - Janet
- Natalie Higashi - Stacy
- Debra McGrath - Dawn
- Katherine Giaquinto - Debbie (as Katherine Shekter)
- Janet Wright - Naomi Bascombe
- Helen Beavis - Mrs. Sillas
- Catherine Black - Sharon
- Ken James - Warden
- Lindsay Leese - Waitress
- Joe Pingue - Granger
- Michelle Risi - Missy
- Richard Blackburn - Guard
- John Boylan - Beryl's Father
- Jeff Clarke - Cop #2
- Toni Ellwand - Mother in Stands
- Jamie McRoberts - Opera Singing Kid
- Jamie McRoberts - Daughter
- Tony Meyler - Guard #1
- Marianne Moroney - Mother
- Don Murray - Reporter
- Robbie Rox - Cesar
- John Vasilantonakis - Kaminsky
- Scott Wickware - Cop #1
- Philip Williams - Cab Driver
- Elijah Wood - The Artful Dodger
- Gerard Cannon - Fagin's Gang
- David Gallagher - Marty Markham
- Jeremy Foley - Spin Evans
- Charles Shaughnessy - Jordan Welsh
- Yancy Butler - Veronica Hulka
- Dan Zukovic - Gladstone
- Brian Markinson - Beckwith Evans
- Lynda Boyd - Stephanie Evans
- Judd Nelson - Jack Hulka
- Tim Considine - Mayor Considine
- Sarah Hyland - Molly
- Lindsay Lohan - Casey Stuart
- Bug Hall - Scout Bozell
- Lainie Kazan - Mrs. Day
- Curtis Armstrong - Bert Miller
- Stephanie Faracy - Mrs. Marlowe
- Alex McKenna - Hannah Zapruder
- 'Weird Al' Yankovic - Weird Al
- Joel Brooks - Principal Norris
- Joel Brooks - Ferguson
- Charlene Tilton - Mrs. Zapruder
- John Bennett Perry - Mr. Zapruder
- Phillip Van Dyke - Kent Marlowe
- John Walsh - John Walsh
- Wink Martindale - Wink Martindale
- Leslie Nielsen - Mr. Penn
- Kirstie Alley - Katherine Lewis
- Dale Midkiff - Thomas Jameson
- Ross Malinger - Bobby Jameson
- Lynn Redgrave - Rogers
- Daryl Mitchell - Raul
- Marcus Toji - Trevor
- Melanie Mayron - Mindy
- Kimberly Scott - Gwen
- Zack Duhame - Kent
- Jesse Moss - Levon Waters
- Ted Atherton - George
- Ted Atherton - Mitch
- Karen Robinson - Sally
- Karen Robinson - Dr. Ericson
- Sabrina Grdevich - Miss Vicky Polite
- Kelly Ripa - Self - Host
- David Stollery - Commissioner Stollery
- Tamsin Kelsey - Mrs. Markham
- Brian Jensen - Mr. Markham
- Richard Side - Mr. Mann
- Laurie Murdoch - Minister
- Michael Sunczyk - Precinct Captain
- Bob Dawson - Officer Petrie
- Simon Longmore - Officer Collins
- Deni DeLory - Charlotte
- Betty Linde - Mary
- Brenda McDonald - Mary's Friend
- Lauren Diewold - Little Girl
- Eileen Brennan - Joe #1
- Joel Swetow - Joe #2
- Arjay Smith - Phil
- Kaley Cuoco - Lori
- John P. Connolly - Dr. Green
- Catlin Adams - Carrie's Mom
- Patrick Kerr - Mr. Wood
- Jake Richardson - Jeff
- Jamie Renée Smith - Young Katherine
- Thomas Crawford - Cupid
- Gregory Hinton - Tiny
- Lindze Letherman - Molly
- Helen Slater - Katherine's Mom
- Yeardley Smith - Gatekeeper
- Rusty Cundieff
- Don French
- Melanie Mayron
- Tony Adler
- Eric Laneuville
- Cindy Smith
- Paul Zindel
- David Simkins
- Mark Kaufman
- Rose Lam
- Natalie Hart
- Jason La Padura
- Debra Martin Chase
- Mike Moder
- Neil Meron
- David Michael Frank
- Craig Safan
Kirstie Alley interpreta a Katherine Lewis en la serie.
Elijah Wood interpreta a The Artful Dodger en la serie.
Keira Knightley interpreta a Gwyn en la serie.
Kimberly Scott hace el papel de Gwen.
Michael Eisner interpreta a Himself - Host en la serie.
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