Suggestions by @ cartmansohana

Steve Martin

as Trent in Total Drama

Bill Murray

as Trent in Total Drama

Philip G. Epstein

as Writer in Stripes (1941)

Humphrey Bogart

as Cody Martin in The suite life of Zack & Cody

+1-2Score: -1

George Lazenby

as G in Best Actor starting with every letter

+5-3Score: +2

Humphrey Bogart

as H in Best Actor starting with every letter

+10-1Score: +9

Humphrey Bogart

as Rick Blaine in Never reboot these characters

+2-0Score: +2

Humphrey Bogart

as General madine in Star Wars Original trilogy in the 50s

+3-0Score: +3

Humphrey Bogart

as Owen Lars in Golden Age Star Wars

Humphrey Bogart

as Luke Skywalker in Golden Age Star Wars

+1-5Score: -4

Humphrey Bogart

as Obi Wan Kenobi in Golden Age Star Wars

+1-4Score: -3

Humphrey Bogart

as C3P0 in Golden Age Star Wars

Margot Robbie

as Carlotta in The Little Mermaid (2021)

+1-2Score: -1

Tom Bosley

as Flotsam, Jetsam in The Little Mermaid (2021)

Humphrey Bogart

as Mr. Darling in Peter Pan

Natalie Portman

as Tiger Lily in Peter Pan

Tom Bosley

as Indian Chief in Peter Pan

Humphrey Bogart

as James Bond in Classic Actors As Modern Movie characters

Humphrey Bogart

as John Wick in Classic Actors As Modern Movie characters