Not really good with pairing up double features, but I'll take a stab in the dark.
S.F.W. and Series 7: The Contenders
Both explore how we allow our lives to be dictated by the media.
It's A Wonderful Life and Miracle On 34th Street
By the end of both movies, they present hopeful ideals in the face of pragmatic and challenging reality.
Asura and Frankenstein
Both are about misunderstood 'monsters' whose treatment received reflects the ugliness of humanity.
Buried and Phone Booth
Watch Buried and mourn, then Phone Booth and rejoice.
Die Hard and Hot Fuzz
First look at how badass John McClane is in Die Hard - then watch how Hot Fuzz tear it all down.