Yes but bears have such thick skulls you would have to go thru the open mouth into the throat if he was that close to you. Otherwise anywhere in the center neck area and make sure you get off as many rounds off as you can before you get knocked down by him.
That is with a handgun, if you have a good rifle just pumping rounds into him. No I have never been attacked by a bear.
I live in rural Alaska, mostly around my area its the smaller Black bear, the larger Brown bears are not very common around here.
I used to haul with me a huge stainless scoped Ruger Redhawk 44mag. when I went fishing, now I carry a 10mm Glock with a hi cap magazine of my own reloads. I believe its better to have a lot of bullets than just a couple of heavy ones that have to hit a certain place.
But arguing there is no comparison with Black bears and Alaskan Kodiak grizzlies, the ones I have seen are like something from Jurassic park. Grenades, got to make some grenades....