obviously peter sellers in dr. strangelove
in kill bill 2 the same guy plays the sheriff at the beginning and esteban at the end. he was pretty amazing as the latter.
Tom Hardy plays twins in a film called Legend
Nicolas Cage and John Travolta play both themselves and each other in face/off
There’s an actor in the LOTR trilogy who plays several different prominent orc characters
Also John Rhys-davies plays both Gimli and Treebeard
also Brett McKenzie played Figwit and Lindir (I had to look these names up; he’s just an extra but also one of the guys from Flight of the Conchords).
favorite
Does Face/Off count. I mean it could get in on a technicality. Nothing better than Travolta pretending to be Nicholas Cage, and Nicholas Cage being well the same.
And then I knew: that this boy, would be a fool, for blondes.
not a movie but garret dillahunt in deadwood
deadwood was the best
Paul Dano in There Will Be Blood would likely qualify.
I Know Who Killed Me is the best movie featuring Art Bell and Awesome Color.
nicholas cage as john travolta was nicholas cage but with even more awkward face touching
Alec Guinness plays 8 members of the D’Ascoyne family in Kind Hearts and Coronets
How could I forget Kind Hearts and Coronets. It’s a British black comedy about British ponces hating each other for money, as played by a knighted aristocrat actor. It’s just about the most British thing imaginable.
I was struggling to describe this so I just uploaded it
such a wonderfully weird film