Suggestions by @jesselee

Bowler Hat Guy (Michael "Goob" Yagoobian)

as Bowler Hat Guy in The Sopranos

Doc Hudson

as Doc Hudson in The Sopranos

Sally (The Nightmare Before Christmas)

as Sally Finkelstein in The Sopranos

Jack Skellington

as Jack Skellington in The Sopranos

White Queen (Emma Frost)

as Emma Frost in The Sopranos

Wario

as Wario in The Sopranos

Princess Daisy

as Princess Daisy in The Sopranos

Amy Rose

as Amy Rose in The Sopranos

King Bowser Koopa Sr.

as Bowser in The Sopranos

Donkey Kong (Character)

as Donkey Kong in The Sopranos

Sonic the Hedgehog (Character)

as Sonic the Hedgehog in The Sopranos

Princess Peach Toadstool

as Princess Peach in The Sopranos

Luigi (Nintendo Character)

as Luigi in The Sopranos

Mario (Nintendo Character)

as Super Mario in The Sopranos

Pinocchio (Shrek)

as Pinocchio ( Shrek) in The Sopranos

Cruz Ramirez

as Cruz Ramirez in The Sopranos

Lightning McQueen

as Lighting McQueen in The Sopranos

Magic Mirror (Shrek)

as Magic Mirror ( Shrek) in The Sopranos

Princess Mindy

as Princess Mindy in The Sopranos

Captain Hook (Shrek)

as Captain Hook ( Shrek ) in The Sopranos