This is a topic I could write at great lengths about. Instead of a wall of text, I think I shall buck the trend and focus on directors that I enjoy revisiting their works, in reverse chronology.
The Russo brothers
If I were to attempt to single out a favorite film it would currently be Captain America: The Winter Soldier. I could analyze the Marvel franchise for hours upon hours, but IMO this is when it went from good to great.
Of course there are plenty of one hit wonders I could re-watch, such as The Princess Bride. There are also a few I can't return to after seeing their later installments, such as the second and third Matrix.