Suggestions by @aloloco

The Wizard of Oz (Character)

as Frank Morgan in Characters actors have played or will play

The Scarecrow (The Wizard Of Oz)

as Ray Bolger in Characters actors have played or will play

The Wicked Witch of the West

as Margaret Hamilton in Characters actors have played or will play

The Cowardly Lion (The Wizard Of Oz)

as Bert Lahr in Characters actors have played or will play

Satan

as Harvey Keitel in Characters actors have played or will play

Samuel L. Jackson

as Samuel L. Jackson in Characters actors have played or will play

John Shaft

as Samuel L. Jackson in Characters actors have played or will play

Uncle Sam

as Samuel L. Jackson in Characters actors have played or will play

Batman Triumphant

as Jack Nicholson in Roles That Actors / Actresses Were ALMOST Casted

Annie Oakley

as Judy Garland in Roles That Actors / Actresses Were ALMOST Casted

Dorothy Gale (The Wizard of Oz)

as Judy Garland in Characters actors have played or will play

Kiara (The Lion King II)

as Blue Ivy Carter in Characters actors have played or will play

Brennan Huff

as Will Ferrell in Characters actors have played or will play

The Ghost of Christmas Present

as Will Ferrell in Characters actors have played or will play

Darrin Stephens

as Will Ferrell in Characters actors have played or will play

Lou Adler

as Will Ferrell in Characters actors have played or will play

DeAngelo Vickers

as Will Ferrell in Characters actors have played or will play

Geryon

as Will Ferrell in Characters actors have played or will play

Jesus Christ

as Will Ferrell in Characters actors have played or will play

Fidel Castro

as Will Ferrell in Characters actors have played or will play