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)
I'm not sure if this is fair game because it's a webcomic, but I've re-read Kill Six Billion Demons multiple times. The art, the little fables underneath, it's all done so well. The drawings regularly burst with detail, and you can spend several moments just noticing different things in a panel. I think the author is in the process of finishing up the last chapter now, but it's a great ride.
I need to revisit long bow hunters again, it has been already around 3 years since the last time, i have been waiting for a good chance of picking up the rest of his run for a decent price.
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.
NextWave! It's kind of my comfort read, because it's very light hearted in a lot of ways that traditional comics aren't. It's very violent and swear-y though.