I decided to do nine old-timey characters from different old-timey themed cartoons and games as ponies from MLP.
 
From left to right:  
Bendy (Bendy And The Ink Machine)  
Mickey Mouse (Disney’s Mickey Mouse shorts)  
Minnie Mouse (Disney’s Mickey Mouse shorts)  
Boris (Bendy And The Ink Machine)  
Oswald The Lucky Rabbit (Epic Mickey, Oswald shorts)  
Alice Angel (Bendy And The Ink Machine)  
Ortensia (Epic Mickey, Oswald shorts)  
Felix The Cat (Felix The Cat)
 
Betty Boop (Betty Boop)
 
Bases link:
 
Starlight Glimmer Base 02 (Bendy)  
Minuette Base 02 (Mickey Mouse)  
Lady Justice Base (Minnie Mouse)  
Starlight Base (not to be confused with Starlight Glimmer) (Boris)  
Manehattanite 01 Base (Oswald the Lucky Rabbit)  
Happy Flutters Base (Alice Angel)  
Silver Spanner Base (Ortensia)  
Fluttershy Base (Felix The Cat)  
Rarity Base (Betty Boop)
 
My Little Pony: Friendship is Magic (c) , Discovery Family and fyre-flye.
 
Bendy And The Ink Machine (c) TheMeatly.
 
Mickey, Oswald, Ortensia, Minnie and Epic Mickey (c) .
 
Felix The Cat (c) Otto Messmer and Pat Sullivan.
 
Betty Boop (c) Max Fliescher.
 
Bases (c) SelenaEde.