They both begin a trip at the post!
Not Z.
Popcorn, of course!
Three. One to post it, the second to post a better punchline in the comments, and the third to complain that it's a repost.
There were no jokes in the Post.
T. Modern pirates are most likely based in Somalia, and T is the most common consonant in the Somali Latin alphabet.
Smiles. There is a mile between the first and the last letter.
Planet
Because they were Russian!
A racehorse because it can take hundreds of people for a ride at once!