Suggestions by @hookey_walker

Paul Shaffer

as Head Flying Monkey in The Wizard of Oz

Garrett Morris

as Mayor of Munchkin City in The Wizard of Oz

Tom Davis

as Auntie Em in The Wizard of Oz

Al Franken

as Uncle Henry in The Wizard of Oz

Laraine Newman

as Glinda in The Wizard of Oz

Jane Curtin

as Miss Gulch in The Wizard of Oz

Jane Curtin

as Glinda in The Wizard of Oz

John Belushi

as The Cowardly Lion in The Wizard of Oz

Bill Murray

as The Tin Man in The Wizard of Oz

Dan Aykroyd

as The Scarecrow in The Wizard of Oz

Chevy Chase

as The Wizard in The Wizard of Oz

Gilda Radner

as Dorothy in The Wizard of Oz