Suggestions by @jakewilson1

Tim Roth

as Charles Davis in Dirty Harry (1991)

Score: 0

Arnold Schwarzenegger

as The Governator in Cars Live Action

Score: +1

Billy Bob Thornton

as Mater in Cars Live Action

Score: +1

Matt Damon

as Lt Tom "Iceman" Kazansky in Top Gun (1996)

Score: +1

Ben Affleck

as Lt Pete "Maverick" Mitchell in Top Gun (1996)

Score: +1

Clint Eastwood

as LT Tom "Iceman" Kazansky in Top Gun (1956)

Score: +2

Cole Hauser

as Lerner in Platoon (1996)

Score: +1

Harvey Keitel

as Staff Sgt. Barnes in Platoon (1976)

Score: +1

Joe Pesci

as Marsellus Wallace in Martin Scorsese Presents Pulp Fiction

Score: +2

James Woods

as Zed in Pulp Fiction (1984)

Score: +1

Chuck Connors

as Captain Koons in Pulp Fiction (1984)

Score: +1

Paul Newman

as Winston Wolfe in Pulp Fiction (1984)

Score: +1

Dennis Quaid

as Private/Sergeant J. T. "Joker" Davis in Full Metal Jacket (1997)

Score: 0

Clark Gable

as Jackie Treehorn in The Big Lebowski in the Golden Age of Hollywood

Score: +3

Humphrey Bogart

as Jeffrey "The Dude" Lebowski in The Big Lebowski in the Golden Age of Hollywood

Score: +5

John Wayne

as The Stranger in The Big Lebowski in the Golden Age of Hollywood

Score: +3

James Stewart

as Winston Wolfe in Pulp Fiction (1974)

Score: +1

Harrison Ford

as Butch Coolidge in Pulp Fiction (1974)

Score: 0

Clint Eastwood

as Vincent Vega in Pulp Fiction (1974)

Score: 0

Steve McQueen

as Mr. White in Reservoir Dogs (1982)

Score: -2