At my present company the upper management is constantly trying to make jokes that the 20-somethings will get. That includes movie references and things which you know some of them don't really get (especially when they say "I'm told you all will find this hilarious"). It shows a willingness of those older, experienced people to adjust their presentation to the "culture" of the current employees. The overall culture of the company is still to have a lot of fun, just the jokes change a little as time goes on.