Who is this favorite person????

Question

1. This man's identity would wake up a weary Robert Frost.
2. The most famous TV mobster has something in common with this man.

Answer 1

Since you have asked this question four times, this better be a decent trivia puzzle and not something lame.
I decided not to report you for multiple postings, though.

I think we need more clues, as no one seems to have gotten this right on any of the questions.