History Tearjerker / HowTheGrinchStoleChristmas

* Max, in the TV special, gets put through the ringer pulling that sleigh. It's especially sad considering he originally thought he was going to be riding it, and quickly had his puppy-like excitement dashed.

!!The 2000 live action movie:
* The song "Where Are You, Christmas?" is a combo of heartwarming and tearjerking. Little Cindy Lou sings about her Yuletide doubts. They don't get some grown-up to do it as a background song, either - that's Taylor Momsen. She looks at her small stocking, and a list saying "Dear Santa, I don't know what to ask for this Christmas." She looks at Mount Crumpit far away. And with the last few notes of the song, we see the Grinch entering his lair, ''all alone.'' Tell me that at some point that didn't twang your emotional strings. The lyrics can especially hit home for older viewers -- with Christmas not being the same as it was when they were kids and missing it. The extended version sung by Faith Hill also has a standout line in the second verse that was not in the movie version: "I'm not the same one. See what the time's done. Is that why you have let me go?" Sad enough sung by an adult, but imagine a 6-year-old girl singing it.
* The Grinch's DarkAndTroubledPast, anyone?
** For the first time in his life, the Grinch was excited about Christmas. He made his own gift for Martha (Sure, he made it from stuff he broke, but it's the thought that counts), and even the old ladies who looked after him told Cindy Lou how nice it was to see him truly in the Christmas spirit. All he wanted was to look nice when he gave Martha his present...
*** To make matters worse, he didn't even ''need'' to change his appearance--Martha May already thought he looked nice. It was only the {{Jerkass}} Augustus's cruel teasing that pushed the Grinch to try shaving.
** The final moments of the flashback wherein the little Grinch struggles to climb away up the enormous snowy mountain, screaming to himself about how he hates Christmas, before eventually standing alone on the mountain. None of this is helped by James Horner's weeping score.
*** Especially since, if you listen carefully as the flashback ends, you can actually hear the Grinch ''crying''.
*** Even worse? This was the last film role of the late Josh Ryan Evans, who played the young Grinch. [[RealitySubtext The last we see of him and he's all alone with a broken heart]].
** The look on young Martha's face when she picks up the Grinch's broken present. You can actually see tear stains on her face.
---> '''Martha, narrating:''' It was a horrible day, when they were so cruel to him...I could hardly bear it.
** The Grinch's true StartOfDarkness: after many failed efforts to hide his bad attempt at giving himself a good shave and his shaving cuts, everyone but Martha in the schoolroom -- '''''including the teacher!''''' -- start laughing at him. Finally, he just completely snaps. Cue MassOhCrap from the class when they realize they've pushed the Grinch too far with their teasing, especially Augustus.
---> '''Grinch:''' Stupid present! Stupid tree! [[PunctuatedForEmphasis I! HATE! CHRISTMAS!]]
** If you really think about it, the teacher probably didn't mean anything by it; she was just chuckling to herself that the Grinch tried to shave himself, and she thought it wasn't that big of a deal. She was likely going to give him a talk about it later, but Augustus's bullying only made her a part of the problem.
** It gets worse when you imagine the heartbreak the two Who biddies who raised him felt when he ran away from home. To emphasize the point, one of them says very sadly, "And that was the last time anyone saw him. The very last time."
* The Grinch has just had the best day of his life, judging eating contests, winning the nog-off, winning the award of Holiday Cheermeister, and winning the sack race. It's not perfect, but he's cheering up and joining in. Then {{Jerkass}} Mayor May-Who spoils the day - twice. [[spoiler: First he gives the Grinch an electric razor to joke about his childhood, then he proposes to Martha in front of him. Naturally, the Grinch ''loses it'' and goes to ruin the Whobilation, [[HoistByHisOwnPetard partly by using the razor to make May-Who "FABULOOOUUS!".]]]]
** It only gets worse when he returns home and screams out "BLAST YOU, WHOS!" and then starts crying, obviously in a lot of pain from all that had happened to him that night and as a child.
** Guess who's among the crowd of Whos when the Grinch goes to the Whobilation? Carnella and Rose Who, the same two Who biddies who raised him since he was a baby (they even made a ''Christmas sweater'' for him!)--so you can imagine the heartbreak they must have felt to see the Mayor humiliate him with the razor and later, the Grinch tearing off the sweater before torching the tree in the town square.
*** To make matters worse, what's the very first thing they say when the finally see the Grinch? "''We missed you.''" And they say it while they're reaching out to hug him with tears in their eyes. They've spent DECADES wishing for their adopted son to come home, and finally thought he was back for good...only to lose him again in just a few hours.
*** As noted on the Heartwarming page, consider that Cindy only nominated the Grinch for the Cheermeister position on the previous day. That means that the Grinch's mothers either spent all night making him a brand-new sweater, or--even sadder--''always had one ready for him in case he came back.''
** Before all this, the Grinch is so misanthropic and traumatized that he fears whether the invitation was just a ploy to humiliate him again by the Whos, tearing himself up on whether he should go or not.
** Cindy's reaction to the whole Whobilation disaster is just ''heartrending.'' Her plan to restore the Grinch's holiday spirit was working so well, and the Mayor ruined it all with his bullying over the Grinch's childhood humiliation and his proposing to Martha in front of him just to get one over on him again. And even worse, the Mayor has the audacity to implicitly blame and shame ''her'' for the whole mess - and in front of her family too - for inviting the Grinch to begin with, when in fact it was ''his'' callous actions that set the Grinch's rampage off in the first place.
-->'''Cindy''': ''(near tears)'' [[BreaktheCutie I just wanted everyone to be together for Christmas...]]
** From the extended version, Martha and Betty are seen competing in the lighting contest. Both sides are neck-and-neck in the contest, lighting up part after part of their Christmas light displays, until Betty lights the final part of hers which clearly puts it superior over Martha's. The judges are very impressed to the point of agreeing with this, and write her name down as the winner, which would finally make Betty's dream of having the best Christmas light display in Whoville and beating Martha (whom she had lost the contest to numerous times in the past) come true. But Mayor May-Who plays favorites and, trying to butter up Martha for the later marriage proposal, disregards the judges' votes, claims that it's a "split-decision", and declares Martha the winner once again, leaving Betty feeling crushed and disappointed, and showing just how corrupt the mayor truly is.
* Once the Grinch reaches the point where his heart grows three sizes, the very first thing he does is to start ''crying his eyes out'', the walls he built up around himself crumbling to dust as he unbottles all the pent up emotional trauma he had been subjected to throughout the years.

** Cindy's reaction to the whole Whobilation disaster is just ''heartrending.''

** From the extended version, Martha and Betty are seen competing in the lighting contest. Both sides are neck-and-neck in the contest, lighting up part after part of their Christmas light displays, until Betty lights the final part of hers which clearly puts it superior over Martha's. The judges are very impressed to the point of agreeing with this, and write her name down as the winner, which would finally make Betty's dream of having the best Christmas light display in Whoville and beating Martha come true. But Mayor May-Who plays favorites and, trying to butter up Martha for the later marriage proposal, disregards the judges' votes, claims that it's a "split-decision", and declares Martha the winner, leaving Betty feeling crushed and disappointed, and showing just how corrupt the mayor truly is.