A "Stone-like" Puzzle

This puzzle is a homage to the early internet mystery game The Stone. Many of its riddles involved interpreting cryptic images, along with a lot of research, leading to some interesting finds. While they did often involve a lot of guesswork to get the exact answer, I dig the simple aesthetic and the knowledge of the world I gained.

All you have to do is answer the question posed by the image below:

Please excuse the semi-cruddy quality of the image. Paint will do that to you.

STARTING NUDGE:

It would be good consider this image in three "sections". One section will give you who "he" is, and the other two will give you the "what". No ciphers (well, maybe in one small case) are necessary, just picture ID with a little word association thrown in.

NUDGE 2:

The sections by the keys on the left or right lead to the "what". The three stacked pictures in the bottom center lead to "him". The gentlemen in the picture are related and held the same position, but "he" is neither of them.

NUDGE 3:

The guys next to the SQUARE and OBELISK are a pair of politicians from the Northeastern US. One of them is currently serving. The "S" on the left is not just an S, but is normally seen as part of a corporate logo. As far as I can tell, "he" doesn't have any breathing problems...

I'll be happy to confirm individual bits if anyone needs it.

• Do you think the rebus tag is appropriate? Jun 14, 2018 at 1:44
• Not in this case, no. If I did miss any tags people would think are appropriate, let me know.
– SKOG
Jun 14, 2018 at 1:46

He is:

Rivers Cuomo from Weezer (doesn't have any breathing problems ;).

What he's Got...

is his Hash Pipe? This was originally a guess based on the syntax of the song lyrics matching that of the question in the picture (i.e: "I got my hash pipe"). The key on the left has a one pound coin on it; the pound sign or hashtag (#) indicates a "key" signature with one sharp, which would be G Major (the key of Hash Pipe). I'm still working out the rest of images to put it all together. Will edit post as I decipher the rest of the clues.