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[[quoteright:297:https://static.tvtropes.org/pmwiki/pub/images/raccoon_deceased.png]]
[[caption-width-right:297: Wish he did, though.]]
* One Sunday strip features Calvin getting ready for a day at school one rainy morning. That's it. No dialogue, no ImagineSpot, no wacky hijinks...and the last two strips feature Calvin staring at the clock, bored and miserable, while Hobbes stares out the window in the rain, waiting for Calvin to come home. Of the three characters (Calvin, Hobbes, and Mom) nobody smiles once.
* One of the earliest story arcs of the strips deals with Hobbes having been stolen from Calvin by a dog. Calvin's sadness over Hobbes' loss really hits home, especially to those readers who had beloved toys lost and stolen as kids. It's also one of the first times in the strip Watterson received fan mail from readers genuinely concerned about Hobbes' wellbeing.
-->'''Calvin:''' ''(wiping a tear)'' What did I ever do to deserve this? ''({{beat}}, then sticks his head out the window)'' '''[[MoodWhiplash WHATEVER IT WAS, I'M]] ''[[MoodWhiplash SORRY]]'' [[MoodWhiplash ALREADY]]!'''
* Rosalyn and Calvin never get along, due to Rosalyn starting her babysitter stint by locking up Calvin in the garage and then in his room. Calvin then retaliates, and they never really find common ground... [[SugarWiki/HeartwarmingMoments until he teaches her how to play Calvinball]].
* The infamous storyline where Calvin and Hobbes find an injured baby raccoon and rally the family together to try to save its life. Unfortunately, they don't succeed.
** As shown above, Calvin's dad reluctantly has to break the news to him. He's not happy about it, especially when Calvin starts to sob in genuine grief.
--->'''Dad:''' At least he died safe and warm. We did everything we could, but now he's gone.
--->'''Calvin:''' ''(sniff)'' I know. I'm crying because out there he's gone, but he's not gone inside me.
** This sorrowful dialogue from Calvin as he and Hobbes witness the raccoon's grave.
--->'''Calvin:''' This [tree] is where Dad buried the little raccoon. I didn't even know he existed a few days ago, and now he's gone forever. It's like I met him for no reason. I had to say goodbye as soon as I said hello. Still... In a sad, awful, terrible way, I'm happy I met him. ''(sniffs)'' What a stupid world.
** Calvin laments how painful and unfair it all is, and ends up being scared by the concept of death.
--->'''Calvin''': He was just little! What's the point of putting him here and then taking him back so soon?! It's either mean or arbitrary, and either way I've got the heebie-jeebies.
** Crossed with a Heartwarming Moment, the arc ends with Hobbes and Calvin ultimately accepting that death is just simply a part of life and then make a promise that they're not going to leave each other.
---> '''Calvin:''' Mom said death is as natural as birth, and it's all part of the life cycle. She says that we don't understand it, but there are many things we don't understand, and we just have to do the best we can with the knowledge we have. I guess that makes sense. ''(hugs Hobbes)'' But don't '''you''' go anywhere.
---> '''Hobbes:''' Don't worry.
** This story has a bit of RealitySubtext to it, as Watterson said it "just wrote itself" when his wife found a dead stray kitten one day.
** What makes this one especially heartbreaking is that it's one of the few times we see Calvin genuinely concerned about someone other than himself, and genuinely upset about something real and very sad, not just a variation on "he didn't get his way".
* The ''Yukon Ho!'' arc starts off as humorous, but then it quickly gets depressing. Hobbes and Calvin get into a scuffle, leading to Calvin storming off and leaving Hobbes to go to the Yukon himself.
-->'''Calvin:''' You can go to the Yukon ''yourself.''
-->'''Hobbes:''' Ha! As captain, I fire you anyway!
-->'''Calvin:''' ''(walking off)'' Good! I'm going home!
-->'''Hobbes:''' [[ArmorPiercingResponse You don't have a home. You seceded, remember?]]
-->''({{beat panel}} as Calvin realizes his mistake)''
-->'''Calvin:''' ''({{facepalm}}ing)'' [[DidntThinkThisThrough My life needs a rewind/erase button.]]
** The next strip shows Calvin walking back home, wondering what'll happen if his parents don't take him back.
-->'''Calvin:''' What if they tell me I can't rejoin the family? They ''have'' to take me back! I'm their [[SelfDeprecation stupid]] ''[[SelfDeprecation kid]]'', right?
** And then the cherry on top: Calvin realizes that Hobbes is lost and frantically goes out to find him. Seeing him so desperate is heartwrenching, especially when he tearfully blames himself for what happened.
--->'''Calvin:''' ''(sniff)'' I hope he's ok. If he hadn't been acting so stupid, I never would've left him. I sure wish he'd come back.
** [[SugarWiki/HeartwarmingMoments Thankfully, his mom and dad go out in the woods to try and find Hobbes]].
* The Christmas strip where Calvin confesses to Hobbes that he didn't get him a Christmas present or a card. [[SugarWiki/HeartwarmingMoments Hobbes wishes him a merry Christmas anyway, and they hug each other]].
* "[[http://i.imgur.com/Pbap0sm.jpg I suppose it will all make sense when we grow up]]."
** For reference; most boys Calvin's age would [[PokingDeadThingsWithAStick poke a dead bird with a stick]]. Calvin ''[[WiseBeyondTheirYears waxes philosophical]]'' about it instead.
** Another bit of RealitySubtext. The dead bird sketched in the first panel was one that Bill Watterson found outside his home.
* The one where Calvin and Hobbes figure out that they can play together all night by dreaming about each other, then go to bed saying they'll see each other soon. Seems more like a SugarWiki/{{Heartwarming Moment|s}}, until the 10th Anniversary compilation where Bill Watterson revealed that he wrote that strip after the death of his cat Sprite, who was the major inspiration for Hobbes' look and personality.
-->''"We can always meet again in dreams."''
* The last strip, especially with the final line being, "[[AndTheAdventureContinues It's a magical world, Hobbes, ol' buddy. Let's go exploring]]!" Pass the tissues, please...
* The family returning home from a trip (on which Hobbes had been left behind at home by mistake) and discovering their house had been broken into. Dad even muses how ''he doesn't feel safe in his own home anymore'':
-->'''Dad:''' A man's home is his castle, but it shouldn't have to be a fortress.
** Later, he talks to his wife about how, during his own childhood, he always trusted his parents to fix everything, and it never crossed his mind that they might not have any idea ''how''...which is the same situation he's in now.
** Meanwhile, Calvin is practically in hysterics trying to find Hobbes because he thinks his best friend has been tigernapped (he even tells his mother that "Hobbes is so trusting," especially since Hobbes is established as a misanthrope). Thankfully, he was not.
-->'''Calvin:''' Mom says Hobbes wouldn't have been stolen because he's not valuable. ''(sits miserably, sniffling)'' Well, ''I'' think he's valuable.
** Calvin's mom's take on the break-in.
-->'''Dad:''' This is something that you always figure will happen to someone else.
-->'''Mom:''' Unfortunately, we're ''all'' "someone else" to someone else.
* The baseball story arc. Calvin signs up for a baseball team due to being bullied by Moe for being the only boy who didn't sign up. However, close to the end, Calvin accidentally catches the ball for the wrong team and makes his team lose. All of the other players cruelly and mean-spiritedly insult Calvin for an understandable mistake, in a way that ''really'' hits close to home if you've been bullied yourself. (One of them even asks the coach if he can ''hit Calvin with the bat''.) The kicker? Due to this name-calling, Calvin asks the coach if he can sign off. The coach's response? "[[KickTheDog Okay, quitter! Goodbye.]]" Thankfully, Hobbes has [[{{Calvinball}} a better idea]] when Calvin gets home.
* There's also the story arc when Calvin has to tell his father that he broke his binoculars, and Dad flies into a tirade lasting for almost an entire strip. [[http://3.bp.blogspot.com/-2OJzukcyodA/T_-xb0A0ehI/AAAAAAAAAD4/JJRBaakLKAs/s640/You+Broke+the+Binoculars.gif At the end of it,]] a tearful Calvin looks up at the man and says, "I have an idea, Dad. Let's pretend I already feel horrible about all this and that you don't need to rub it in anymore." [[MyGodWhatHaveIDone Even Dad looks heartbroken by that one.]]
** What's worse is that throughout the story up to that point, Calvin is genuinely worried about how angry his father will be, and it almost makes the reader wonder if his fear is just making things seem worse in his head. ''It's not.''
* "'''[[https://pianosapress.files.wordpress.com/2014/04/kazam.jpg Ka]]''''''''[[https://pianosapress.files.wordpress.com/2014/04/kazam.jpg ZAM!]]'''''"
** Watterson comments in the tenth anniversary book that "imagination is not always appreciated."
* In one strip, Calvin gets sick and as his mom prepares to call the doctor tells him that he won't have to miss school because it's Saturday. Calvin responds [[OOCIsSeriousBusiness with a weak "I know"]]. Understandably, his mom races to the phone immediately.
** The night before, Calvin has a stomachache and calls for his mom. She mutters that he'd better ''[[PlayingSick really]]'' be sick to be getting her up at 2 AM, [[TemptingFate and then she hears him throwing up in bed]], causing her to shout, "[[BeCarefulWhatYouWishFor I didn't mean it]]!"
** Also, Hobbes shows NoSympathy as Calvin, still sick, lays awake in bed fretting about if he'll go to the hospital or if he's dying. To be fair, Hobbes himself doesn't want to catch Calvin's bug too, but still...
* Susie wants to be friends with Calvin, or at least play with the only kid on their neighborhood block. Calvin refuses, due to Susie being a girl. He has made her cry, tossed apples and pinecones at her, and refused to play house her way. While he is sincere at times, like when he thanks her multiple times for finding Hobbes and keeping him safe, Calvin is too mean the rest of the time.
** The arc where Calvin, as said before, makes Susie cry is sad in its own right, but this moment counts:
-->'''Susie:''' Sticks and stones may break my bones, but words will never hurt me. ''[[BeatPanel (she starts walking away proudly, but then her face falls)]]'' Yeah, right.
** Add the implication from several story arcs that she's a staunch perfectionist who often panics that a failure in ''first grade'' could ruin her chances of getting into a good college, and Susie really is prime [[TheWoobie woobie]] material.
* One that takes a moment to sink in is the Sunday strip that walks Calvin through the various hardships and frustrations of a typical school day. When his mom kisses him goodnight and promises that "tomorrow's another big day!", Calvin's only response is a defeated sigh. Watterson's comment on the strip in the 10th Anniversary book sums it up:
-->''I've never understood people who insist that childhood is an idyllic time.''
** An earlier strip had the same theme, where Moe punches Calvin and knocks him into the mud for no reason, then leaves laughing, leaving a miserable Calvin to remark, "People who are nostalgic for childhood were obviously never children."
** Yet another strip begins with Calvin angrily complaining about having to go to school even though he hates it, only for Dad to tiredly tell him that in that case, ''he'' can go to work all day to provide for the family, with the only reward being the griping of a whiny kid. Cut to Calvin standing at the bus stop with a sour look on his face.
---> '''Calvin''': It's nice to know there's so much to look forward to in life.
* In one strip, Calvin asks Dad why grown-ups never play outside, and Dad answers that grownups have to justify "playing outside" by calling it "exercise", rating and scoring it, and doing it whenever they'd rather not.
--> '''Calvin''': That sounds like a job.
--> '''Dad''': Except you don't get paid.
--> '''Calvin''': So play is worse than work?
--> '''Dad''': [[{{Understatement}} Being a grown-up is tough]].
* Calvin's life in general, probably even more so than [[ComicStrip/{{Peanuts}} Charlie Brown]]. At least Charlie Brown had friends like Linus who were generally nice to him. Calvin is just a complete misfit. In [[https://chutzpah.typepad.com/.a/6a00e55180ed5c883400e55400be968834-800wi one strip in particular]], he outright says that [[IJustWantToHaveFriends he wishes he had more friends]].
* Read the comments of the [[https://www.facebook.com/photo?fbid=376110037209855&set=a.261773351976858 final strip]] of the ''ComicStrip/BloomCounty'' crossover. More than a few people were reduced to TearsOfJoy or had SandInMyEyes.
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