5. The Good Shepherd (2006)
De Niro has only directed two films, the second of which was his long-standing passion project covering the early history of the CIA (and supposedly intended to continue into a second film, not yet realized). It's possible I'm giving his supporting role in his own movie extra credit because De Niro directed the thing, but I think that's fair; anyone bemoaning De Niro's lack of late-period taste or ambition should check this one out. Even if you find the movie from De Niro the director a little restrained, you'll see a nicely understated turn from De Niro the actor, as a general who helps form the CIA and later laments the lack of dignity in dying "from the feet up."