Suggestions by @redgth

Jimmy Stewart

as Dr Curt Connors in Sam Raimi's Spiderman Trilogy 1950s

Score: +1

Thomas Mitchell

as Ben Parker in Sam Raimi's Spiderman Trilogy 1950s

Score: +1

Debbie Reynolds

as Mary Jane Watson in Sam Raimi's Spiderman Trilogy 1950s

Score: +1

Jimmy Stewart

as Ben Parker in Sam Raimi's Spiderman Trilogy 1950s

Score: -1

Marlon Brando

as Harry Osbourne in Sam Raimi's Spiderman Trilogy 1950s

Score: +1

Jimmy Stewart

as Dr. Curt Connors in Sam Raimi's Spiderman Trilogy 1950s

Score: +1

Claude Rains

as Norman Osbourne/ Green Goblin in Sam Raimi's Spiderman Trilogy 1950s

Score: +1

Orson Welles

as Dr Otto Octavius in Sam Raimi's Spiderman Trilogy 1950s

Score: +1

Lee J. Cobb

as J. Jonah Jameson in Sam Raimi's Spiderman Trilogy 1950s

Score: +1

Tony Curtis

as Peter Parker/Spiderman in Sam Raimi's Spiderman Trilogy 1950s

Score: +1

Van Heflin

as Cobb in Silverado

Score: +2

Barbara Stanwyck

as Stella in Silverado

Score: +2

Randolph Scott

as Emmett in Silverado

Score: +2

James Coburn

as Slick in Silverado

Score: +2

Glenn Ford

as Paden in Silverado

Score: +2

Richard Jaeckel

as Tyree in Silverado

Score: +2

Audie Murphy

as Jake in Silverado

Score: +2

Woody Strode

as Mal in Silverado

Score: +2

Natalie Wood

as River Tam in Firefly

Score: +1

Louis Armstrong

as Shepherd Booker in Firefly

Score: +1