As the movie association game continues, we decided against watching The Royal Tenenbaums: Criterion Collection and instead followed Owen Wilson to Armageddon: Criterion Collection. The next movie hasn't been picked yet, but there's tons of people to branch out onto now. Might go to Bruce Willis next and watch the full Die Hard trilogy or maybe follow Liv Tyler or Ben Affleck to a comedy. Who knows...the movies watched thus far are:

Armageddon (Owen Wilson and TBD)
Permanent Midnight (Ben Stiller and Owen Wilson)
Keeping the Faith (Edward Norton and Ben Stiller)
Rounders (Edward Norton - Starting Film)

URL: Armageddon (1998)