It’s SPECULATION, but if he put the gun under his chin and shot straight up, wouldn’t that blow most of the front of his face off?
A .22, no, not likely.
The 9mm would do some damage if the bullet travelled through the facial bones at the front of the head, but would be slower to kill. A round to the roof of the mouth might do that too if it fragmented.
Short of jacketed hollow points or a frangible round, the damage would likely be mostly distortion, not destruction if the bullet or fragments did not exit the face--an 'exit' wound.
Something on the order of a shotgun is needed to 'blow the face off'.