I think we are going to see Kier on-screen in the next season; and I believe it will be played by Sean Penn.
I realized upon a rewatch of "The Secret Life of Walter Mitty" that Ben Stiller has re-used the pilot as Mr. Drummond. Obviously, Adam Scott is also featured in this movie (albeit, as an antagonist).
His reverence towards the actor in giving him such a role leads me to believe that not only would the casting be appropriate, it could also could be meaningful.
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Even better would be if first we see Crispin Glover "as Kier" being paid to portray Kier, only to reveal a holographic image of Chris Penn talking about Crispin being payed to play Kier while having a wax figure carved of himself; to then finally reveal Sean Penn apologizing for the inaccurate portrayals of himself, the real Kier Eagan.