Suggestions by @ben_quigels

Barbara Stanwyck

as Queen Cersei Lannister in A Game of Thrones in Old Hollywood

Score: +1

Orson Welles

as King Robert Baratheon in A Game of Thrones in Old Hollywood

Score: +1

James Dean

as Jack Dawson in Titanic 1997 (In Old Hollywood)

Score: +1

Sal Mineo

as Renly Baratheon in Game of Thrones If It Was Made During the Golden Age of Hollywood (Pre-1960s)

Score: +1

James Dean

as Jon Snow in Game of Thrones If It Was Made During the Golden Age of Hollywood (Pre-1960s)

Score: +1

Henry Fonda

as Ned Stark in Game of Thrones If It Was Made During the Golden Age of Hollywood (Pre-1960s)

Score: +2

Katharine Hepburn

as Catelyn Stark in Game of Thrones If It Was Made During the Golden Age of Hollywood (Pre-1960s)

Score: +2

Clark Gable

as Petyr Baelish in Game of Thrones If It Was Made During the Golden Age of Hollywood (Pre-1960s)

Score: +2

Judy Holliday

as Lizzy Calvert in Titanic 1997 (In Old Hollywood)

Score: +1

John Mills

as William McMaster Murdoch in Titanic 1997 (In Old Hollywood)

Score: +1

Leslie Howard

as J. Bruce Ismay in Titanic 1997 (In Old Hollywood)

Score: +1

Sybil Thorndike

as Rose Calvert in Titanic 1997 (In Old Hollywood)

Score: +1

Kirk Douglas

as Brock Lovett in Titanic 1997 (In Old Hollywood)

Score: +1

Charlie Chaplin

as Thomas Andrews in Titanic 1997 (In Old Hollywood)

Score: +1

Laurence Naismith

as Edward J. Smith in Titanic 1997 (In Old Hollywood)

Score: +1

Joan Crawford

as Ruth DeWitt Bukater in Titanic 1997 (In Old Hollywood)

Score: +1

Cary Grant

as Caledon Hockley in Titanic 1997 (In Old Hollywood)

Score: +3

Thelma Ritter

as Margaret Brown in Titanic 1997 (In Old Hollywood)

Score: +1

Thelma Ritter

as Septa Mordane in Game of Thrones as Classic Hollywood

Score: +1

Montgomery Clift

as Jon Snow in Game of Thrones as Classic Hollywood

Score: +1