OK, I'm stumped as to the ID of #1.

As for #2, another hint... I suppose he was able to overlook quite a few potential lassies from his crow's nest like perch while singing with the cranes, even though he's a night owl himself.

If you can't guess #2 from that, Naemanson will have to come up with some more clues, because, other than giving out the first five letters of his name, I would be hard pressed to come up with anything else.