Here is my contribution. King Henry II of Jerusalem, in his other incarnation as the ... Mantis Lord! Crusader States (Lusignan Kingdom of Cyprus): silver gros petit of Henry II, ca. 1285-1324 Ex-Classical Numismatic Group, USA, eAuction 435, Lot 447. PCGS certification pending, submission #186815, received 5/11/2019. @Oldhoopster aptly made that comparison, and I've not been able to unsee it ever since.
I think the Kingdom of the Bosporus has a claim to bad portraits. Here's one from Thothorses (285-308)/ The coin is dated explicitly below the bust on the other side, 296/7. That means the man on the other side is a Roman ruler at the time--but who? The coin is MacDonald 644/2. Because coins from the Kingdom of the Bosporus are dated we can identify the Roman emperor if there was only one emperor at that date. But in 296/7 the first tetrarchy was in power and, absent an identifying legend, we can not be sure which Roman it is. I don't think the portrait is good enough to help!
Agreed! This is Pharsanzes on the left, but is that Trebonianus Gallus, Valerian, or Gallienus blowing bubbles on the right?