Culture Give-Ins?

I spoke recently with a friend of mine. He's a brilliant fellow, studying the deep areas of philosophy and religion and focusing in on how the two intersect. It has become more and more apparent to me lately that much theory is taught and learned, yet most people graduate with little to no true understanding of what the message of Christ-in-culture truly is.

As I spoke with my friend, he brought an interesting point up: Christian sub-culture, as it has been deemed, has decided that it, for the most part, is most satisfied with partitioning itself off with its own music, book, and self-help section that all reflect a Christianized version of a secular concept. In my mind, I feel that the Christian sub-culture, itself, has proved to engage very few people, satisfying many with warm feelings of sentiment, Thomas Kinkade-branded theology, and a reactionary stance on nearly everything. In fact, the largest and strongest graduate program at my current university is apologetics.

Why do we react instead of act? Where have the culture makers gone? Where is the Lewis, Chestertons, and Augustines of our time? Why have so many influential Christian authors seen fit to merely preach to the choir and stand in the background? Why have so many students, like myself, seen fit to listen to the cultural backlash against beliefs and not met them head-on?

I am convinced that God works through culture. In my major, that is called contextualization. It is a ministry happening all over the earth, showing with definitive evidence that the gospel is for all and redeems culture. But my question comes down to this: why have we not contextualized a message for the "Christian" nation of America; for the politicians; for those who need to hear it? Why have I not made this effort?