I've shot a couple bears straight on. One was a charge and I was lucky enough to hit the sow right beside the eye and kill her on the spot. I was just holding on fur and praying at the time.
Second one was a large boar grizzly. It was sitting on a bank on his rear end looking at me. It was a close shot, maybe 75 yards. The body was directly inline with my plane of site and I had a good rest on a tree. I aimed just below the chin at the base of the neck where it meets the sternum. Bear did a back flip at the shot trying to bite at the exit wound and then bolted. He made it about 100 yards.
I don't think I would aim for a head shot intentionally on a black bear for the skull/trophy aspect. I would probably wait for a better shot or pass unless I was thinking I was going to get chewed on I guess. The brain is a pretty small target.
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There are some who can live without wild things, and some who cannot. Aldo Leopold
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