If he'll watch B&W, try at least one version of:yeah he doesn't mind B&W and he might actually go for Steel Magnolias.
The Scarlet Pimpernel
The Three Musketeers
The Prisoner of Zenda
If he likes discussing movies, try one of the older versions and a more modern one.
Also, I should add some of the delightful Roger Corman/Vincent Price costume pieces:
The Pit and the Pendulum
The Masque of the Red Death
The Haunted Palace
And Nick Adams being outacted by Boris Karloff's little finger in Die, Monster, Die!
How can you ignore 'The Raven' (1963) Roger Corman film with Vincent Price, Peter Lorre, Boris Karloff and a really young Jack Nicholson?
Valley of Guangee (sp?) (That's 'Gwangi'. I loved that film, like a really early 'Jurassic Park'. With the cutest little Eohippi)
'Kind Hearts and Coronets' with Obi-Wan Kenobi (Alec Guinness, not that kid) as practically everybody. For that matter, how about: 'Bridge On The River Kwai'?He's watched Dracula I think (I distinctly remember the comment of OMG Dracula is Saruman!)
And, if we're doing 'classics', I'm assuming that he's seen 'Old Yeller'?
That movie has everything--Fairbanks Jr., Massey, Mary Astor from The Maltese Falcon, and Madeleine Carroll from The 39 Steps in a delightfully snarky role.