Is 'play had to have' a complete sentence? Do you mean 'They' or is 'Play' someone's name?
Either way, you never say 'would of'. It should be 'would have'. "I would've gone home" actually means "I would have gone home", not "I would of."
So a) it's "Would have", "should have", "must have", "had to have", etc.
And "He would have had to have had to smoke weed to be like he was" is too long. It should be "He would have had to smoke weed to be like he was."
<i>He (would have) (had to) smoke weed [...].</i>
That's what the sentence breaks down to. (Would have) indicates the action he took ('smoke') and (had to) indicates the tense (past tense). When you break down the phrase it the parts become (would have) and (had to), not (would have had to). If you think of them as two different parts then you'll see that you don't need to add another 'had to' at the end.
So b) "He would have had to smoke weed to be like he was."
Hope that helps
