I reckon he's got to be a Bond afficienado, so would have been delighted at there being a new Bond (and let's face it, who didn't like the Daniel Craig in a speedo scene?). That was 2006 and 2008. I can also see him going for the comic book based films - Batman Begins and The Dark Knight would probably appeal, as would Hellboy and X-Men and The Incredible Hulk, stuff like that. The Bourne trilogy probably worked for him. All of these have been relaeased in the last two or three years, or at least the final parts of the series have.

Failing all that, he could be into arty stuff - A Scanner Darkly (2006) would fit into 'cool', or something similarly unusual.