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First of all, I think we all understand that it should have been "have" and not "of."
Secondly, no one but a pot-head would think that "Play had to have," was a sentence, even in colloquial English. Had to have what?!
Thirdly, I don't think the sentences "Play would have had to have smoked weed," and "Play would have had to smoke weed," mean the same thing, exactly.
"Play would have had to have smoked weed," means that, in the hypothetical past, there was reason to believe that Play had smoked weed but... I will say more about this, later.
"Play would have had to smoke weed," simply means that, in the hypothetical past, Play smoked weed but... I will say more about this, later.
Fourthly, I still don't think the sentence makes any sense. The word "would," in this case, is used to determine a hypothetical past. "I would have done this," makes no more sense, as a sentence, than "If I were in town." If I were in town... then what?! I would have done this... but what?! Play would have had to smoke weed... but what?!
Lastly, you're probably better off asking your hot English major although I have a sneaking suspicion she will not have any insight into this. Furthermore, I suspect that she might not even be interested in the problem... Not all English students are fascinated by the subtleties of English grammar...
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