Most of the time, Bill Watterson's Calvin and Hobbes was a straightforward comedy, set in equal parts a nondescript American suburb and its protagonist's imagination. While it's got more than its share of memorable lines and genuine wisdom, C&H was rarely out to tug on anyone's heartstrings. There are two exceptions to that rule.
One is a full story arc from March 1987, in which Calvin tries to rescue a baby raccoon. The other is a one-shot from late in the comic's run, as one of Watterson's more experimental Sunday strips. Both are quiet meditations on death, as Calvin confronts mortality through encounters with animals.
This isn't going to be a particularly funny article, but here are the best Calvin and Hobbes comics about grief. Watterson mentioned in passing in The Calvin and Hobbes Tenth Anniversary Book (1995) that, in his imagination, Calvin's home is built right up against the edge of a nature preserve or national forest. As such, Calvin has a nearly infinite amount of woodland to explore in his free time, with or without Hobbes.
That's part of what inspires any number of C&H's occasional deviations into environmentalism. It's also what led to the storyline that began on March 9, 1987. Calvin and Hobbes find a baby raccoon out in the woods, injured and with no sign of his parents.
Without any better ideas, Calvin runs to get his mother, and they spend the next couple of days trying to nurse the baby raccoon back to health. Unfortunately, the baby raccoon doesn't make it. "At least he died warm and safe, Calvin," his dad tells him.
"We did all we could but now he's gone." "I know," Calvin says. "I'm crying because out there he's gone, but he's not gone inside me." It's an unusually sentimental piece from Calvin and Hobbes, particularly for a story that involves Calvin's mom and dad. It's rare to see them as unequivocally supportive as they are in the baby raccoon arc, as both of them are often deliberately depicted as ambivalent about parenthood, but this is a rare glimpse of some genuine sentimentality in C&H.
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