It depends on his interests.
If he likes comedies there are some real gems like A Boy and His Dog, The Absent-Minded Professor, Monty Python, and A Funny Thing Happened on the Way to the Forum, and my personal favorite The Court Jester.
For super heroes, there's the originals of Batman and Superman.
There are a bunch of classic musicals like Grease, Paint your Wagon, Willy Wonka, Singing in the Rain, Fiddler on the Roof, West Side Story, and all of the Rodgers and Hammerstein classics.
Horror is not my genre so I wouldn't be good at recommendations, but there are classics like Jaws, Psycho, Rosemary's Baby and the extensive collection of campy Universal Monster flicks (Dracula, The Mummy, Frankenstein, The Wolf Man, ect.).
Will the little voice in the back of my mind screaming "This is a bad idea" please yield the floor. --Mikey
Chivalry be hanged, and so will you.