For something like this:

What would be the most effective way to do this? Best to do an image, or is there a way to achieve this with CSS without a bunch of hacks/extra markup that I dont know about?
Also the shadow only has to work in IE9, FF, and Chrome
You would do so using pseudo-elements and the
box-shadowproperty. I have done up an example for you here: http://jsfiddle.net/joshnh/NWnXw/This works in IE9 and up.