Suggestions by @edmarx88
738 suggestions
Martin Short
as Professor Marvel in The Wizard of Oz (1999)

Tony Shalhoub
as Tin Woodman in The Wizard of Oz (1999)

Whitney Houston
as Glinda in The Wizard of Oz (1999)
Catherine O'Hara
as Wicked Witch of the West in The Wizard of Oz (1999)
Jean Smart
as Marion Wormer in Animal House 1978 Remake
Patti LuPone
as Wicked Witch of the West in The Wizard of Oz (1999)

John Lithgow
as Wicked Witch of the West in The Wizard of Oz (1999)

John Lithgow
as Professor Marvel in The Wizard of Oz (1999)
Bill Murray
as Professor Marvel in The Wizard of Oz (1999)

Kristen Dunst
as Dorothy Gale in The Wizard of Oz (1999)
Brian Doyle-Murray
as Uncle Henry in The Wizard of Oz (1999)

Darren McGavin
as Uncle Henry in The Wizard of Oz (1999)

French Stewart
as Scarecrow in The Wizard of Oz (1999)
Blake Clark
as Uncle Henry in The Wizard of Oz (1999)
David Hyde Pierce
as Tin Woodman in The Wizard of Oz (1999)

Richard Kind
as Cowardly Lion in The Wizard of Oz (1999)
Mimi Rogers
as Glinda in The Wizard of Oz (1999)

Paul Dooley
as Uncle Henry in The Wizard of Oz (1999)

Colin Mochrie
as Tin Woodman in The Wizard of Oz (1999)
Diedrich Bader
as Scarecrow in The Wizard of Oz (1999)