From sequels earlier we move to remakes, only remakes done by the very same director who made the original. Why direct the same film again? I have no idea. Some questions I just don't ask.
Oscar Micheaux: Birthright - 1924 and 1939
Cecil B. DeMille: The Squaw Man - 1914, 1918 AND 1931
Alfred Hitchcock: The Man Who Knew Too Much - 1934 and 1956
Leo McCarey: Love Affair - 1939 and 1957 (retitled An Affair to Remember
Woody Allen: September - 1987 and 1987. He made the movie first with Maureen O'Sullivan, Charles Durning and Sam Shepard, then made it again with Elaine Stritch, Denholm Elliott and Sam Waterston in their roles. Why? Maybe he was bored.
Michael Haneke: Funny Games - 1997 and 2007
Martin Scorsese: Goodfellas 1990 Casino 1995. Oh, wait a minute...