Westworld’s MIB is in Host form with full abilities. Lost’s MIB can change into Smoke Monster only when on the island but otherwise remains with his powers.
Round 1: In the Delos parks.
Round 2: On the island.
Round 3. At Stonehenge. (UK)
Round 4: In Times Square while a gigantic squid is also attacking.
Round 5: Fighting on top of Mount Roraima.
Bonus round: Boy in White from ‘From’, vs both Man in Blacks, setting is Fromland/Fromville and he has all his abilities.
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I never got around to watching Lost, so IDK about that, but at first I misread the prompt as Westworld’s Man in Black vs the Men in Black. It was actually a decent question in my head since K and J’s tech advantage is probably offset by their general goofiness. I think it comes down to numbers. J probably gets taken out right away about 70% of the time if he’s in character, as the Man in Black will just shoot him while he’s investigating, trying to talk or asking questions, but I think K has no compunction about just shooting the Man in Black the second he figures out how dangerous he is and it comes down to just ruthlessness and who gets the drop on who.
Round 4, I’m going with the squid 9/10, though I assume in this round they end up teaming up to confront Ozymandias.
