Suggestions by @jamesthethinker

Toucan Sam

as Cereal Mascots in Mount Rushmores

Score: +5

Count Chocula

as Cereal Mascots in Mount Rushmores

Score: +3

Alfred Molina

as Supervillain Actors in Mount Rushmores

Score: +4

Kevin McNally

as Joshamee Gibbs in Untitled Pirates of Caribbean Sequel

Score: +1

Zoe Saldaña

as Anamaria in Untitled Pirates of Caribbean Sequel

Score: +1

Johnny Depp

as Captain Jack Sparrow in Untitled Pirates of Caribbean Sequel

Score: +1

Smokey Bear

as Bears in Mount Rushmores

Score: +2

Po

as Bears in Mount Rushmores

Score: +3

Little Bear (character)

as Bears in Mount Rushmores

Score: +2

Jason Lee

as Supervillain Actors in Mount Rushmores

Score: +4

Michelle Pfeiffer

as Supervillain Actors in Mount Rushmores

Score: +3

Josh Brolin

as Supervillain Actors in Mount Rushmores

Score: +6

Cruella De Vil

as Disney Villains in Mount Rushmores

Score: +7

Captain Hook

as Disney Villains in Mount Rushmores

Score: +2

Pacman

as Video Game Characters in Mount Rushmores

Score: +5

Master Chief

as Video Game Characters in Mount Rushmores

Score: +4

Gil Kenan

as Director in Where in the World is Carmen Sandiego

Score: +1

Alan Ritchson

as Agent Rock Solid in Where in the World is Carmen Sandiego

Score: +1

Big Show

as Agent Rock Solid in Where in the World is Carmen Sandiego

Score: +1

Melissa Fumero

as Carmen Sandiego in Where in the World is Carmen Sandiego

Score: +1