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The optimistic interpretation of this happening is that it's a sign of some kind of personal growth inbetween time.
Gatsby: I read at 20, and thought it varied from dull to mildly interesting. I reread about 15 years later and it was just astonishingly good. Pretty sure it's not the book that changed 
On Arrival: well, um, as several of my friends have learned (at great length), I'm a little irrational on this subject. I thought it was superb the first time I read it. The second time I decided it was a work of absolute, utter genius.
My notes immediately after a second reread of Arrival (spoilers, of course, and these are very sketchy and needs to be much more fleshed out):pic.twitter.com/9kPpU45h9I
Excuse me, of course I mean "Story of Your Life", which was turned into the movie "Arrival" (good, but not in the same class, AFAICT).
_Gatsby_ is a caution against *recklessness*. This is utterly opaque to the tropical young man, who is evolutionarily predisposed to irrational risk taking. Young men don't stan Gatsby because they are literally recklessness engines. (Typically.)
Please understand that by tropical I meant (to type) typical.
Recklessness is not tropic, but isotropic. 
I read that in high school and it was amazing, I haven't gone back to it
Man, I read Gatsby when I was 20ish too and found it dull and uninteresting.. maybe his time for a re-read -- you've given me hope!
Gatsby was one of those for me too. Another, amazingly, was The Scarlet Letter. I consider it very underrated and still pertinent today.
I've never read that one. What's good about it, now? Maybe it explores some issues that the 20-year-old you wasn't keyed in to yet?
I had to read it in high school. I thought it was terrible then. Now, I just think it's inappropriate for that age =P
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