I know this looks like a very specific scenario, but there are many ways in which damage counters can be spread (Munkidori), so I think there is definitely potential to pull off a multiple-prize turn
Before we begin, I am making an executive decision: Humans don't count
Otherwise, the values here, and the new offerings are sufficiently powerful
Another variable: Artists aren't immortal, at least not physically, and so it will eventually be impossible to track them down for a signing
(If you cast Flameskull this way, you can't play the other card, and vice versa.) This creature can't block
Base Set 1st Edition Charizard Holo (1999, US) Why its special: The original grailshadowless, foil, and stamped with a bold 1, symbolizing early print quality and scarcity, widely considered the most iconic Charizard Pokmon card ever printed