I'll ignore the multitude of shmups and fighting games that I innevitably return to in the hopes of completing 1cc runs or otherwise "getting gud" at - and I'll also ignore the many games I've had to revisit over the years for work - and instead focus on a couple comfort games that I tend to replay at least once a year!
Gitaroo Man is so short and sweet - it only takes about an hour to see it through from start to finish, and always cheers me up; such a silly little romp all about true love, the power of music, and working to achieve your dreams. Who could resist?
Whenever I'm sick and restricted to days recovering in bed (which happens more often that I'd like) I usually re-read The Hobbit, The Princess Bride, or Treasure Island because they're pretty cozy, swash-buckling adventures - and in that same vein I find myself returning to Chrono Trigger in those same periods of recovery. I'm not really swept up in the usual 16-bit console RPG swooning (sorry Lufia-heads; Rise of the Sinistrals kinda sucks), but the pacing and structure of CT are so TIGHT!?? it's a real breeze to run through, and with enough variety in terms of party and equipment loadouts to make a playthrough different enough from the last (at least to MY hazy, virus soaked brain).
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I think SotN is the sort of game that cries out to be replayed semi-regularly, and especially with it approaching the spooky season, it's as good a time as any to backdash through Dracula's castle yet again!