Un-Identified Beer steins

I recently aquired two of what are obviously beer steins and would like to know their approximate age and era. I would also like to know who the man is on the top of one stein, and what the wording on the other is about...maybe a beer name? Though they are different, their bottoms have the same pattern and I found them in the same shop together. The handle is broken off on one the steins, but it's still an interesting piece.

More pictures are available if needed.

Any help is appreciated as I could find nothing on these items on the internet.

Thank you,

Alfred