This can all be done from within the DrawItem event of the control. I've never drawn an image to the control before, but I'd imagine that you could with e.Graphics.DrawImage().
In terms of showing some items in bold or plain, you can just create a conditional statement around the e.Graphics.DrawString() method to show some items in bold. I actually spent the time putting together an example for you, but it appears that the web server ate my post. If you still need an example, please let me know.