I think his choices stink! To me it seems that he mostly appreciates movies that he saw in his childhood or youth. Like, almost nothing from the 1970s and after, whaaat!?
Don't get me wrong, I love many old movies (e.g. The Treasure of Sierra Madre, Mutiny on the Bounty, The Third Man, Citizen Kane, A Night at the Opera, Gaslight...), but I don't think the pre-1970s was the golden age of cinema or anything like that. And BTW, The Searchers and Vertigo are among the most overrated films ever IMO! (Love Bernard Herrmann's soundtrack on the latter, though.)