I have been thinking about this, there are some videogames i usually revisit every year or so like some older Fable and AC games. I dont reread comics that much, outside some outstanding issues like The brave and the mold from Tom King’s Batman or Lemire’s Green Arrow, but those have been more occasional rereadings more than a yearly ritual.
I often go back to my Alan Moore dc collection, and Jimmy Corrigan: the smartest kid on earth (it’s depressing but very real and hits the way a great classic Hollywood film does)