Suggestions by @maxthecat67

Edward Van Sloan

as Doc Hudson in Universal's Cars (1936)

Bela Lugosi

as Lightning McQueen in Universal's Cars (1936)

Conrad Veidt

as Michael Keaton in Classic Celebrity that are similar to Modern Celebrity

Fredric March

as Michael Keaton in Classic Celebrity that are similar to Modern Celebrity

Max Schreck

as Pennywise in It (1937)

James Whale

as Director in Five Nights at Freddy's (1943)

Paul Robeson

as Golden Freddy in Five Nights at Freddy's (1943)

Conrad Veidt

as Foxy the Pirate Fox in Five Nights at Freddy's (1943)

Charlie Chaplin and Marion Davies

as Bonnie and Chica in Five Nights at Freddy's (1943)

Marion Davies

as Chica the Chicken in Five Nights at Freddy's (1943)

Roscoe Arbuckle and Charlie Chaplin

as Freddy and Bonnie in Five Nights at Freddy's (1943)

Charlie Chaplin

as Bonnie the Bunny in Five Nights at Freddy's (1943)

Roscoe Arbuckle

as Freddy Fazbear in Five Nights at Freddy's (1943)

Mae Clarke

as Social Worker in Five Nights at Freddy's (1943)

Cab Calloway

as Cabbie in Five Nights at Freddy's (1943)

Rex Ingram

as Pharmacist in Five Nights at Freddy's (1943)

Gloria Stuart

as Kim in Five Nights at Freddy's (1943)

Clark Gable

as Sparky's Diner Waiter in Five Nights at Freddy's (1943)

Jean Arthur

as Ice Cream Lady in Five Nights at Freddy's (1943)

Fay Wray

as Cindy in Five Nights at Freddy's (1943)