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This is an original question.

Russ and Kess are chatting. Russ says he saw Kess cracking away on his computer and wondered "what is the significance of 23986?".
Kess said "it might make your analogy true, but will it cause my syndrome?"
Russ said "it might meet Mr Munroe's 1866".
Kess replied, "it's true, but could he answer what if it is big enough?"

Can you tell me:
Russ's surname,
Mr Munroe's website and his qualification to answer Kess's question
the fastest time Kess's near name sakes "run" - and the pilot. (optional)
Finally, what is 23986

Hint (cryptic)

I could have used a famous short Danish title

Hint - location

Both of their theories can only occur in orbit

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This appears to be a bunch of references to semi-related concepts, clued by partial names and loosely interlinked.

Russ and Kess are chatting. Russ says he saw Kess cracking away on his computer and wondered "what is the significance of 23986?".

23986 is the ID number of Lego's white teapot piece.

Kess said "it might make your analogy true, but will it cause my syndrome?"

"Russ" is philosopher Bertrand Russell, and the analogy here is Russell's teapot, a hypothetical teapot orbiting in space (used to talk about unfalsifiable claims and burden of proof).
"Kess" is NASA scientist Donald J. Kessler, and the 'syndrome' here is the Kessler syndrome, a theoretical scenario where space pollution leads to increasing collisions, generating more and more debris.

Russ said "it might meet Mr Munroe's 1866".
Kess replied, "it's true, but could he answer what if it is big enough?"

"Mr Munroe" is Randall Munroe, author of well-known webcomic XKCD. His comic number 1866 is on Russell's teapot, and he also used to work at NASA.

The "near-namesake" mentioned in the questions near the end is

the Kessel run from Star Wars, which Han Solo apparently ran in just over 12 parsecs. (This is implied by context to be meant as a unit of time, even though in reality it is a unit of distance.)

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  • $\begingroup$ How did you find some of these facts out? $\endgroup$
    – PDT
    Commented Nov 8, 2020 at 15:38
  • $\begingroup$ @PrinceDeepthinker Research? I'm familiar with XKCD and Russell's teapot, and had heard of the Kessel run -- the others were just things I looked up. $\endgroup$
    – Deusovi ♦
    Commented Nov 8, 2020 at 15:41
  • $\begingroup$ Oh right it is just that other than Rusell's teapot the other facts seem very obscure to me and 'ungooglable'. $\endgroup$
    – PDT
    Commented Nov 8, 2020 at 15:44
  • $\begingroup$ Well done. Randall's previous employment and a possible explanation of the tag are the only things left. These are relatively trivial to find with the excellent answer above. $\endgroup$
    – Crighton
    Commented Nov 8, 2020 at 15:53
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a few small comments to finish

Title

A small mistake I am afraid it is meant to be the the translation of Danish "Leg godt" which is "play well" not "let's play" - of course "Leg godt" was turned into a brand - LEGO - which then informs the part number for the teapot. It should probably have been "Play Well - A Cosmic Scandi Drama" which might have avoided the clues.!<

Website

As correctly suggested it is XKCD by Randall Monroe. If you visit you will find a link to his other work top left. He has a "What If" section where he provides proper answers to bizarre questions like how big a hole would you need for the whole atmosphere to be contained, or how would you use a firepole from the moon to the earth, and one of my current favourites how a small plane would perform on all the planets of the solar system (and some moons).!<

Occupation

Mr Munroe is an ex-NASA scientist/engineer, hence the hint as to how he could help!<

Many thanks for giving this a go.

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