Suggestions by @mrtenebris

Steve Purcell

as Executive Producers in Sam & Max: The Movie

Score: +1

Steve Purcell

as Producer in Sam & Max: The Movie

Score: +1

Jared Emerson-Johnson

as Composer in Sam & Max: The Movie

Score: +1

Sophia Lillis

as The Geek in Sam & Max: The Movie

Score: +2

Kevin Hart

as Max in Sam & Max: The Movie

Score: +2

Charlie Sheen

as Sam in Sam & Max: The Movie

Score: +2

Steve Purcell

as Writer in Sam & Max: The Movie

Score: +1

Edgar Wright

as Director in Sam & Max: The Movie

Score: +1

Nolan North

as Jimmy Two-Teeth in Sam & Max: Freelance Police

Score: +1

Jim Carrey

as Shemp in The Three Stooges

Score: +4

Roger Craig Smith

as Leonard Steakcharmer in Sam & Max: Freelance Police

Score: +1

Jeff Bennett

as Leonard Steakcharmer in Sam & Max: Freelance Police

Score: +1

Nolan North

as Leonard Steakcharmer in Sam & Max: Freelance Police

Score: +1

Tom Kenny

as Leonard Steakcharmer in Sam & Max: Freelance Police

Score: +1

Bolo Yeung

as Piston Hondo in Punch-Out! (Movie Adaptation)

Score: +2

Mike Tyson

as Mike Tyson in Punch-Out! (Movie Adaptation)

Score: +2

Keith David

as Sandman in Punch-Out! (Movie Adaptation)

Score: +3

Dwayne Johnson

as Super Macho Man in Punch-Out! (Movie Adaptation)

Score: +1

Jason Momoa

as Bald Bull in Punch-Out! (Movie Adaptation)

Score: +1

Anthony Carrigan

as Soda Popinski in Punch-Out! (Movie Adaptation)

Score: +1