I always replay Grim Fandango around November 1-2, to coincide with the actual Day of the Dead (besides, it's a great way to spend my birthday a few days later!
)
Other games I replay repeatedly are TLJ (or only certain parts sometimes, given its length), Sam & Max Hit the Road, DOTT, Myst, Riven, MI series and BS1.
I replayed GK3 last year with the complete points list to see if I could get the perfect score, only I kept running out of time at the very beginning of the Day 2 2-5 pm time block to do everything I was supposed to!
Also, I'm surprised by all the actions I missed the first time and would have
never otherwise even considered doing!
Talk about thorough investigation!