Suggestions by @mikeypascual

Jeff Bridges

as 1980's in Actors who could be or could have been Kang the Conqueror

Christopher Walken

as 1980's in Actors who could be or could have been Kang the Conqueror

Steven Berkoff

as 1990's in Actors who could be or could have been Red Skull

Adolfo Celi

as 1970's in Actors who could be or could have been Red Skull

Christopher Lee

as 1970's in Actors who could be or could have been Red Skull

Donald Pleasence

as 1970's in Actors who could be or could have been Red Skull

Julian Glover

as 1980's in Actors who could be or could have been Red Skull

Max von Sydow

as 1980's in Actors who could be or could have been Red Skull

Adolf Hitler (Wolfenstein)

as Jürgen Prochnow in Which characters should actors have played in the 90's?

Anthony Hopkins

as 1990's in Actors who could be or could have been Red Skull

Paul Freeman

as 1990's in Actors who could be or could have been Red Skull

Jürgen Prochnow

as 1990's in Actors who could be or could have been Red Skull

Christopher Walken

as 1990's in Actors who could be or could have been Red Skull

Bill Nighy

as 2000's in Actors who could be or could have been Red Skull

Alan Rickman

as 2000's in Actors who could be or could have been Red Skull

Michael Nyqvist

as 2010's in Actors who could be or could have been Red Skull

Til Schweiger

as 2010's in Actors who could be or could have been Red Skull

Christoph Waltz

as 2010's in Actors who could be or could have been Red Skull

Thomas Kretschmann

as 2010's in Actors who could be or could have been Red Skull

Ralph Fiennes

as 2010's in Actors who could be or could have been Red Skull