A London coin dealer told me that the rare Proof Churchill crowns were nicer. I have seen a couple of them offered for sale at many times the price you will pay for the usual pieces. From the photos, they don't look that much better to me.
If you are looking for ugly examples of the human face, just about any medieval hammered British coin will qualify. This is Henry VI. They all pretty much looked the same in those days. This might be worse. This is Henry II, although it was actually issued on behalf of Richard I (a.k.a. Richard the Lion Heart). Richard cared a lot more for his French holdings than "boring old England." He spent less time in England, about 9 months, than any other British monarch. This is a modern political token. The portraits are supposed to be Kennedy and Johnson. The artwork on 19th century political tokens was quite good sometimes, but the modern stuff is usually pretty bad.
Would the 1984 Los Angeles Olympics commens be considered hideous if they don't actually have heads to look at? I always believed they'd look much better as counter stamped satire tokens: "Good For One #0 Haircut At The Tower Of London Barber shop."
It is such a different looking coin, but I could never put my finger on why. You may have answered this for me.
It was really a matter of poor medieval artistry. No one made fun of the king in those days unless they were prepared to defend themselves, go to prison, leave the country or perhaps face beheading. The changeover occurred during the reign of Henry VII. (ruled 1485 to 1509) The first Henry VII coins looked like this. in the opening years of the 16th century, the coin portraits looked like this. The coins were still hammer struck, but the artwork greatly improved.
I don’t think the cartoonish Kennedy - Johnson portraits were intentional, although they may have been. The same company put out a Nixon - Lodge token as well, and it is similar.