Yep @Orielensis Bhartrdāman as mahakshatrapa, silver drachm Head of king right, date behind head: (off flan) Chaitya (3-arched hill), river below, crescent moon and sun above, Brahmi legend around ' rajno mahakshatrapasa rudrasenaputrasa rajno mahakshatrapasa bhartrdamnah'
This one is a bit tricky, so I'll give a hint. The three dots in the left field represent stones and are significant.
I was just about to give another hint, but @Severus Alexander is absolutely correct. It is St. Stephen: Bishopric of Halberstadt, under Gerno von Schembke, AR bracteate, 1169–1177 AD. Obv: + S–STEPHANVSPROTOMARTI; bust of St. Stephen facing between three stones and star. Rev: negative design. 25mm, 0.83g. Ref: Berger 1324; Slg. Bonhoff 483.
Actually, there is no difference. It's simply still debated whether Gero came from the noble family von Schochwitz, the family von Schermke/Schermbke/Schembke, or whether those two families were identical. The sources seem to be ambivalent here, and therefore you'll find different names in the respective scholarship and numismatic catalogues.
Bingo! A quick search of "lowly worm" in the CT search box would have found it. Here's the coin. Surely this is a competitor for the Worst Portrait Ever: Phocas, AE pentanummium, Constantinople. (Note the reverse is upside down in this image.) Your turn, @Orielensis!
We had a couple of tricky ones now, and to speed the game up again, let's continue with something less peripheral. Who knows this guy?
I do not know the origin or year of the coin, but the countermark looks similar on a coin I seen before, the countermark was a bust of Cleopatra, very similar to the bust on yours?