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.
All-Star Superman - whenever I’m having a tough time this comic will always cheer me up.
Also anything Neil Gaiman wrote. Marvel 1602, Mr. Punch, and of course Sandman and its many offshoots. There is so much detail in those stories that I catch something new every time I read them.