Note: only David Simon could answer questions 1 and 2 for you. That being said, here's my humble opinion:
1) What happens to Marlo? He wasn't in the montage.
I think there's a couple of ways you could look at this. One being, at the end of season 5 he was out of the game. So it would make sense that he wasn't in the montage. The problem with that theory is that Marlo showed flashes of not wanting to be out of the game at the end of the last episode. There's a great quote from Laura Miller @ Salon.com about The Wire (see below) not being a traditional story because normal stories end, but The Wire always gave you the sense that the story would keep going long after individual characters left. To me, this is how I reconcil Marlo not being featured - he's out of the game. Like the very old saying goes - the King is dead, long live the King. Marlo's out, there's plenty more to take his place.
2) When Sydnor was talking to the Judge, what was that all about?
Ok, the quote I was talking about:
Laura Miller at Salon dot com wrote:
"The Wire" is also not like the crime novels produced by some of its most celebrated contributing writers (George Pellecanos, Dennis Lehane, Richard Price) because, as is only proper, those books deal in questions answered and narratives resolved. Novels end, but the vast, fascinating, unspooling mess that is the Baltimore of "The Wire" can have no conclusion. The storytellers may stop telling it, but the story itself will go on. If every last character we've loved and hated in the series over the past five years were to roll over and die, it would still go on, with us or without us.
I always viewed that part of the montage as demonstrating that the game continues long after individual players leave. When the show started, McNulty was the salty vet while Sydnor was the younger cop learning the ropes. Season 1 starts with McNulty having that same conversation with the Judge. Season 5 ends with Sydnor having the conversation with the judge. If it went 5 more seasons, some young cop they introduced in the make-believe season 6 would be having the conversation with the judge after Sydnor left.
3) The song at the 'pretend' wake of McNulty, (yes I know it was in an earlier season too), was it definately The Pogues? I know it was a Pogues record but was it them who sang that version?
The easiest of your questions to answer. Check out:
Marlo is in the Montage is he not, he is walking about in his new life in construction. At the party he leaves and walks down to the street where he sees the kids on the corner and they have no idea who he is.
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