This is gonna sound pretty stupid but...how do I tighten a newschool headset? I got my first newschool bike and I've taken the headset off and on, tightening every bolt I can find but there is still noticeable play in the headset/fork assembly. Sorry for the stupid question.

Threadless headsets are simple. The top bolt that threads into the starnut, inside the steertube of the fork, is what "tightens" the headset. The bolts that run crossways through the stem tighten the stem to the steer tube.

1) Make sure the side bolts are all the way loose. If you don't, you'll pull the starnut outta the fork.

2) Begin tightening down the top bolt until there is no side-to-side or back-and-forth play in your headset.

3) Once it is adjusted, tighten down your crossbolts and you're good to go.

I still cant seem to tighten it. Something must be wrong with it. I've tightened the top bolt as tight as it will get (to tight) and cant get the play out of it. Could it be stripped or something?

Your starnut may have slipped upward or was never mounted deep enough initially. This would allow the top bolt to bottom out and effectively put an end to any pulling power it needs to load the bearings. Check that measurement.

There is a fancy starnut seating tool that measures this distance, your LBS will no doubt have one, but since I don't own one I just eyeball it and seat the star nut with a spark plug socket for a driver.

You can also get spacers if the steer tube is too long, I needed 1 spacer under the stem for my WTP forks with FSA headset. Worked a treat.

Thanks it was the spacer. There was one there but it was not big enough.