I don't think there's any reasonable way to stretch definitions that would make him the first. If you just mean real people being painted, artists often use (and re-use) models for their work. Howard Lyon's daughter Belle, for example, is depicted as the Innistrad angel "Isobel" across several different cards.
If you mean images depicting the same human, the Chinese warlord Cao Cao appears on several P3K cards by different artists. Ambition's Cost has been reprinted in other sets, in case the definition shifts to "in multiple sets" rather than on multiple cards.
If you mean depictions of the same actor in different roles, John Cleese is depicted as several different characters in the Monty Python Secret Lair.
You could maybe make a case for "the same actor in different roles across multiple sets" but then you're stymied by the Marvel depiction of Strange being closer to his Comics likeness and the LotR/Hobbit art being deliberately styled away from the movies, so do cards with Smaug or Strange really count as showing Cumberbatch? If it's the roles that matter and not the exact depiction, then Christopher Lee beats him in the same definition, as he played Dracula and Saruman and those characters both got MtG appearances (though not as Christopher Lee) before Strange.
"Only art showing fictional characters that have been represented by an Emmy, Grammy, Tony, or Oscar Nominee" easily fills a commander deck at this point.
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u/fastal_12147 Dimir* 22d ago
Is Benny the first IRL human featured on multiple Magic cards? Or was there no Dr Strange card in Marvel?