Mail to the Chief (television) Two-hour television movie aired on The Wonderful World of Disney on April 2, 2000. A struggling president begins an anonymous e-mail correspondence with a middle-schooler, Kenny, who is having trouble in his civics class, but provides savvy political advice to the chief executive. Directed by Eric Champnella. Stars Randy Quaid (President Osgood), Bill Switzer (Kenny Witowski), Holland Taylor (Katherine Horner), Dave Nichols (Senator Harris), Ashley Gorrell (Heather). Filmed on location in Toronto.