Suggestions by @conordawson99

Little John

as Bing Crosby in Characters golden age stars could have played

FAKE

as Bing Crosby in Characters golden age stars could have played

Thomas O'Malley

as Bing Crosby in Characters golden age stars could have played

Dandy "Jim" Crow

as Bing Crosby in Characters golden age stars could have played

Donald (Thomas and friends)

as Bing Crosby in Characters golden age stars could have played

Ray (The Princess and the Frog)

as Bing Crosby in Characters golden age stars could have played

Prince Eric

as Bing Crosby in Characters golden age stars could have played

Uncle Sam

as Jerry Colonna in Characters golden age stars could have played

Zazu (The Lion King)

as Jerry Colonna in Characters golden age stars could have played

Mayor of Halloween Town

as Ed Wynn in Characters golden age stars could have played

Genie (Disney)

as Ed Wynn in Characters golden age stars could have played

Bing Bong

as Ed Wynn in Characters golden age stars could have played

Santa Claus

as Ed Wynn in Characters golden age stars could have played

King Candy (Turbo)

as Ed Wynn in Characters golden age stars could have played

Jedi Master Yoda

as Ed Wynn in Characters golden age stars could have played

Jafar (Disney)

as Richard Haydn in Characters golden age stars could have played

Zazu (The Lion King)

as Richard Haydn in Characters golden age stars could have played

Sir Hiss

as Richard Haydn in Characters golden age stars could have played

Mufasa (The Lion King)

as Christopher Plummer in Characters golden age stars could have played

Guy-Am-I

as Christopher Plummer in Characters golden age stars could have played