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The Episode is written by Diana Fresco and directed by Tim Burton. It guest stars Alan Arkin as Mr. Giggle, Eric Idle as a Cop, Tom Hanks as the Opera Manager, Tim Allen, Tim Conway and Don Knotts as the Prop men, John Candy as a Pedestrian paying for the Cello Player, John Selya as a Cello Player, Brian Stokes Mitchell as an Angry Pedestrian, Kathy Bates as an Opera Singer and recurring Stars Robin Williams as Mr. Roing, Jim Henson as Mr. Sclomper and Frank Oz as Mr. Zoingpler.
The Audience Members at the Puppet Theater are caricatures of D.B. Sweeney, Josh Weinstein, Bill Oakley, George Meyer, Richard Sakai, James L. Brooks, Matt Groening, Sam Simon, Jon Vitti, John Swartzwelder, Conan O'Brien, Mike Reiss, Dan Greaney, Judy Rothman Rofe, David Mirkin, David X. Cohen, Jeff Martin, Al Jean, Ian Maxtone-Graham, Rich Moore, Michael Jeter, Stephen Sondheim, Alf Clausen, Wes Archer, David Silverman, Tim Conway, Don Knotts, Jim Reardon, Mark Kirkland, Richard Raynis, Greg Daniels, Wallace Wolodarsky, Andrew Lloyd Webber, Alan Menken, Howard Ashman, John Hughes, John Lasseter, Dan Castellaneta, Don Sahlin, Tim Rice, Brad Bird, Ken Keeler, Donick Cary, Jonathan Collier, Richard Appel, Jay Kogen, Betty G. Birney, Mike Scully, Joe Ranft, Robert Lopez, Jeff Marx, Marc Wilmore, Tony Geiss, Judy Freudberg, Jim Henson, Frank Oz, Jerry Juhl, Pete Doctor, Richard Hunt and Jerry Nelson.
The Idea was pitched and written by Diana Fresco. Tim Burton was involved in directing the Episode. He recalls it as a "Metaphor of Animation, Heart and Comedy all combined into one". Matt Warburton suggested the twisted endings for Sleeping Beauty and Three Little Pigs and assigned Jon Vitti to write the Sleeping Beauty ending and George Meyer to write the ending for Three Little Pigs. The Hilarious Medicore Marionette Puppet Show version of Jack and the Beanstalk was written by John Swartzwelder. In a DVD Commentary, he proclaims it as the "Funniest Contribution he ever wrote for Madeline". According to Frank Oz, D.B. Sweeney told everybody to draw their favorite Characters from any Episode of Madeline whenever they want, Matt Groening drew Ellie from Madeline and the Science Project, James L. Brooks drew Lord Cucuface from Madeline and the New House, David Silverman drew Pepito from Madeline and the Pirates, George Meyer drew Lulu from Madeline and the Show Off, Judy Rothman Rofe drew Nicole from Madeline and the Talking Parrot, Jim Henson drew Chloe from Madeline and the Old Violin, Frank Oz drew Danielle from Madeline and the Soccor Star, Jon Vitti drew Anne from Madeline and the Can Can Cliques, Bill Oakley and Josh Weinstein drew Mr. Sclomper and Mr. Zoingpler in Madeline and the Case of the Haunted Train Station, John Swartzwelder drew Janine in Madeline in New York, Jeff Martin drew Sylvie in Madeline and the Wright Brothers, Matt Warburton drew Monique from Madeline and the Greeks, Robin Williams drew Mr. Roing from Madeline and the Treasure Hunt, Al Jean and Mike Reiss drew the Mean, Nasty, Horrible Hats, Jay Kogen and Wallace Wolodarsky drew Janine and Lulu from Madeline in New York and Marc Wilmore drew Nona in Madeline and the Magic Carpet.