Suggestions by @jesselee

Ben Solo (Kylo Ren)

as Kylo Ren in Pee-wee's Playhouse

Emperor Sheev Palpatine (Darth Sidious)

as Emperor Palpatine in Pee-wee's Playhouse

Anakin Skywalker (Darth Vader)

as Darth Vader in Pee-wee's Playhouse

The Blue Fairy

as Blue Fairy in Pee-wee's Playhouse

Stromboli

as Stromboli in Pee-wee's Playhouse

Shere Khan

as Shere Khan in Pee-wee's Playhouse

Jiminy Cricket

as Jiminy Cricket in Pee-wee's Playhouse

Kaa The Snake

as Kaa in Pee-wee's Playhouse

Madame Leota

as Madame Leota in Pee-wee's Playhouse

Kaa

as Kaa in Pee-wee's Playhouse

Blackbeard

as Blackbeard in Pee-wee's Playhouse

Davy Jones

as Davy Jones in Pee-wee's Playhouse

Hector Barbossa

as Hector Barbossa in Pee-wee's Playhouse

Cinderella (Disney Character)

as Cinderella in Pee-wee's Playhouse

Snow White (Disney character)

as Snow White in Pee-wee's Playhouse

Magic Mirror

as Magic Mirror in Pee-wee's Playhouse

Hades (Disney)

as Hades in Pee-wee's Playhouse

Batman

as Batman in Pee-wee's Playhouse

Spooky Spoon

as Spooky Spoon in Pee-wee's Playhouse

The Shape Japer

as The Shape Japer in Pee-wee's Playhouse