The eightball was done the same way as the wine bottle. Take a closer look and you'll see that it renders away when shot, and the invisible func_breakable shoots rock gibs!
If you make the "material type" for the func_breakable
glass, it should look pretty good imo.
There is also a field in the func_breakable for "gib model" which you could make a nice custom gib model--see milkshape--matching the bottle. I've never used that field, so I'm not sure if it works... so if it doesn't, use an env_shooter to "fire" the custom gib.
If you don't know how to model, Lots of people here will make them for you, like
Rimrook and others.
Rim knows how to animate too, so maybe he could make an animated breaking bottle, but I'm not sure about that