[[caption-width-right:185:"Oh dear. I'll have to stay here for always, and no one will ever see my lovely red paint ever again."]]
* "The Sad Story of Henry/Come Out, Henry!" is this in spades. As a result of refusing to leave the tunnel, Henry is bricked up by the Fat Controller "for always and always and always" (although in the US Version, It was only "until you're ready to come out!"). By then, he becomes sad and miserable that no one would ever see his paint again and and that he is never being allowed to journey out again. The publishers of the original novel found the ending so downbeat they only sold Awdry's work so long as he created a happy ending via "Edward, Gordon and Henry/Henry to the Rescue".
** In the ''Series/ShiningTimeStation'' episode: "Does it bite?", Mr. Conductor did not blow his whistle to begin the story because he was too choked up about Henry and his punishment. As he blurts out to the kids in tears, "But I must warn you. It's a very sad story."
** The atmosphere and music is perfectly-executed. After the tunnel is sealed, it goes all quiet, birds are chirping, trains pass-by and Henry is unsure of himself. Then the background theme goes very sad as Henry realizes how stupid he's been, he's all alone, and it's too late to set things right.
** Speaking of next episode, there's the scene where Henry laments on his misbehavior and wondered if the Fat Controller could ever forgive him and let him out of the tunnel.
* In "Thomas' Train/A Big Day For Thomas", Thomas had nearly cried after realizing he wasn't coupled to his train. As soon as he returns to the big station, everyone was talking angrily about the incident just [[JerkassRealization until they noticed how sad Thomas was]].
* The beginning of "Troublesome Trucks/Foolish Freight Cars" where James (as pictured above) remorsefully cries about all of the trouble he's caused with the coaches, particularly mending a hole in one of them with a passenger's bootlace. The tears from his eyes definitely show how terribly sorry he was for his actions.
* One scene of "Thomas and the Guard/Thomas and the Conductor" has Henry moaning of his poor condition to Thomas, who was very dismissive of the issue, bluntly telling him that he's "[[NoSympathy too fat/slow and he needs exercise]]". You have to feel for Henry for his current condition.
* From "Thomas, Terence, and the Snow/Terrence the Tractor", Thomas gets himself stuck on the snow and then realizes how silly that he was for breaking his snowplough just right before he begins to cry.
* After constant failings, the Fat Controller sadly informs Henry that he'll have to replace him if his health doesn't improve in "Coal/Henry's Special Coal". Henry, and his driver and Fireman seem pretty choked up by that, and even the Fat Controller seems to take every action to avoid it happening. [[spoiler: Thankfully his Welsh Coal is brought into the situation.]]
* In "Toby and the Stout Gentleman/Toby the Tram Engine", the passengers wish Toby one last goodbye after his controller decided to close the line, leaving Toby in the shed lonely and unwanted. [[spoiler: That is until his driver wakes him up for good news: an important letter of a certain stout gentleman.]]
* In "Thomas In Trouble", there's Thomas sadly leaving the line after the new policeman brands him a "regular law breaker".
* In "Thomas and Trevor/A New Friend for Thomas", Trevor lets out a tear due to the fact the day's work at the harbor was over.
* The ending of "Dirty Work/Diesel's Devious Deed" where The Fat Controller sends Duck to Edward's station after Gordon, Henry, and James made accusations of Duck telling the trucks false stories and names. Duck lets out a tear on his eye, knowing that his friends and (seemingly) even The Fat Controller have turned against him just as Diesel, who had made those names in the first place, watches him with a sinister grin on his face.
* Henry feeling devastated when a forest was decimated by a storm in "Henry's Forest". Toby feels very bad for him, explaining to Sir Topham Hatt that the forest was a special place for Henry.
* The ending theme of "All At Sea" as the narrator said "Duck still wonders about the lands beyond the horizon, but he enjoys being with friends most of all and I think he knows that sometimes the best travels are those we can only dream about. Don't you?"
* The latter half of "Granpuff" when Duke is left behind and Falcon and Stuart head off to their new home. Think of it as someone being separated from his own children. Now that, is a real heartbreak.
* Mrs. Kyndley tearing up in "Make Someone Happy" when her daughter wasn't able to visit her.
* Salty's pining for the sea in "Salty's Secret".
* In "Thomas and the Birthday Picnic", there's Thomas becoming sad after failing to find a perfect place for Dowager Hatt's birthday picnic. It's even sadder when he realizes that he ran out of ideas, thus upsetting the Hatt Family, complete with letting off a low sad whistle.
* In "Thomas and the Statue", there is the scene where Thomas sadly clears the snow with the snowplough after realizing that his ego about him being the statue had alienated his friends.
* "Toby's New Shed" has Thomas eagerly attempting to do a charitable deed for Toby by helping make a new roof for his shed, only to be confused when Toby doesn't seem too keen on the idea. When the job is done and Toby is downbeat, he doesn't understand and asks what's wrong. Toby somberly explains he liked having his old leaky roof, as birds were able to come in and take shelter, his home was their's, and a guilt ridden Thomas watches as rolls sadly into his new shed alone. [[spoiler: Luckily Thomas fixes this by arranging a bird house to made right next to his shed.]]
* There's a moment in "Thomas and the Rainbow" where Thomas, after obsessing over finding the end of a rainbow and thus neglecting his friends, becomes derailed. Seeing Percy on another line, he shouts and whistles for help, but Percy puffs on, seemingly taking no notice and leaving Thomas behind. Thomas sadly remembers that, because he was rushing to find the rainbow's end, he brushed Percy aside when he wanted to talk earlier. Because of his silly obsession, Thomas has lost his best pal and is stranded without hope.
** [[spoiler: But this is not the case. The rest of the episode turns into one long heartwarming moment, as we learn that Percy, in fact, did hear Thomas' whistle, and was puffing on because he was in a hurry to get help! The message is passed from Percy to Harvey via a large number of other characters, all of whom are anxious to help their friend. Even more heartwarming because the helping characters include several others whom Thomas had spurned earlier.]]
* In "Duck and the Slip Coaches", there's Duck left alone in the sheds very sad because James had stolen his idea of bringing in the slip coaches for the passengers.
-->'''Duck''': "But I told James about the slip coaches. It was...my idea."
** It's no secret to the fandom that Emily is quite a BaseBreakingCharacter. However, when she came back to the sheds and found them completely full (as Duck was sleeping there for the time being), one can't help but feel sorry for her. And if that isn't enough, the next night, Duck is there again, and Henry takes up the last berth, leaving Emily outside again. Worst of all, ''no one else pays her any mind at all!'' Honestly, this was just taking the "Emily replaced Duck!" spiel too far.
* In "No Steam Without Coal", there's Timothy left upset over Bill and Ben's remarks about him being [[AllOfTheOtherReindeer no fun and is the odd one out]], making some feel that the twins' teasing were taken too far.
* "Best Engine Ever" has Emily falling into depression as she feels [[AlwaysSomeoneBetter Caitlin is better than her at everything]], and no matter how much other engines try to raise her spirits it just doesn't work. Even [[JerkWithAHeartOFGold James]] tries to help her, but it's all for naught.
* "Springtime for Diesel" has a surprisingly poignant one. After seeing Daisy was sent to the Dieselworks after he bumped her and hearing she might not be able to be fixed, Diesel lashes out at the others all day. However, at night, he comes into the Dieselworks to a seemingly asleep Daisy and, after a bit of stuttering, finally manages to speak his mind.
-->'''Diesel''': "I'm sorry for shunting into you the way I did, Daisy. I really didn't mean to cause you any trouble...but so what if I did give you a little bump? [[FreudianExcuse Other engines aren't nice to me, so why I should be nice to other engines?]] And they blame me for everything! But... [[SincerityMode I hope you can be fixed.]] I wish I could do something to make everything alright again. I like you...although after this...I don't suppose you'll ever want to be my friend."
** The next day, Daisy is fixed thanks to new springs being delivered to the Dieselworks. But although Daisy is happy to be back, she treats Diesel coldly as she leaves, leaving him rather upset. Thankfully, things get better after that.
* On a meta level "A Shed for Edward" has the titular character move out of Tidmouth Sheds and to a new one at Wellsworth, so he can keep Philip company. To fans of Edward, this effectively seals his fate as DemotedToExtra for the foreseeable future.
* Thomas' increasing jealousy towards Stanley in ''The Great Discovery'' as Stanley starts doing his regular jobs, fraternizing with the other engines, and sleeping in his berth at Tidmoth, leaving Thomas feeling left out. The final straw comes when when Stanely takes Thomas' place on supervising the Great Waterton restoration project. Thomas then decides to make Stanley look foolish by giving him a long freight train too heavy for him to pull. Unfortunately, the prank backfires as the coupling snaps and the trucks race down the hill, veering into a siding and crashing into the newly-built Great Waterton tower, and poor Thomas is left shunned.
* The Fat Controller receiving the telephone call that Thomas has been lost at sea in ''Misty Island Rescue''.
** Percy's growing worry as chances of Thomas being found diminishes. When he ''does'' find Thomas their reunion is a CrowningMomentOfHeartwarming.
* Luke [[spoiler:and Victor]]'s backstories in ''Blue Mountain Mystery''. GOOD GOD.
** A meta example: The fact that this movie was Michael Angelis' swan song as the narrator of the show.
* Stephen trying to find his special job in ''King Of The Railway''. Being a refined version of one of the first engine designs built, he spent most of his early life as TheAce, however in the modern world, Stephen is slow, outdated and unable to pull even small loads current steam engines can. He is rejected every place he tries to prove his worth (despite sympathetic treatment from Paxton and Skarloey) and finds his old mines to have closed down, lamenting sadly he now has no place on the railway.
* ''Tale of the Brave'':
** Right after the [[spoiler:Scrap Heap Monster incident. It ends with Percy completely rejecting Thomas AND James.]]
*** On the same coin, Thomas still wants to make amends, but it doesn't go well at all.
** While they're looking for him, Thomas thinks that Percy is [[spoiler:leaving Sodor forever on Gator's boat. After the initial moment of horror, he rushes to the docks, only to find the boat is already leaving. He whistles and screams for the boat to stop, but they don't hear him. As a last ditch effort, he gets Cranky to snag the boat with his hook, but the crane nearly falls off the docks while pulling the ship back to the port.]]
*** Making it worse is Ben Small's delivery in the UK dub. You can hear his voice ''breaking'' with this particular line:
--->'''Thomas:''' You CAN'T let him leave! ''This is an '''EMERGENCY!''' ''
** [[spoiler:Gator's goodbye. Seriously, Percy looks/sounds so sad through the whole thing, as opposed to Hiro's departure.]]
** Most of the scenes involving Thomas and the Fat Controller (whether directly or indirectly) feel this way, especially because this is the strictest he's acted in years. The worst one of all, though, is after [[spoiler: the dynamite scene, where the Fat Controller shouts at Thomas and sends him away, not having seen enough to know that Thomas was simply trying to save everyone from getting destroyed.]] It's a gut punch at its finest, because more often than not, his harsh words towards Thomas are mostly justified. His behavior towards Thomas also feels much more strict than towards the other engines this time around, which makes things feel worse still. In fact, quite a few fans, prior to the special's release, expected the Fat Controller to state his intent to sell Thomas to the highest bidder, even if for scrap, as he had become that much of a liability.
** Sailor John indirectly accusing Thomas of taking the treasure. Thomas' expression as the sailor rolls away in Skiff really seals it.
*** The worst part is that Sailor John and Skiff usually appeared not long after something happened to dishearten Thomas, and his mood improved quite a bit whenever he met with them. But now even that was taken from him...
** The scene where [[spoiler:Sir Topham Hatt tells Thomas he can't take part in the Shunting Challenge due to his accident, and that Percy has to take his place. Sir Topham looks legitimately ''heartbroken'' during this scene, like a parent telling his ill child that he can't come on vacation with the rest of the family. It doesn't help that Percy is worried about competing, and Ashima coming in to say goodbye before they all leave for the Mainland. The scene ends with Thomas alone at the Steamworks looking miserable and heartbroken.]]
* ''Journey Beyond Sodor''
** Thomas being [[spoiler:kept at the steelworks against his will is just Heartbreaking. What makes it worse is when he [[IWantSong sings about how he just wants to go home]] and misses all his friends, including [[JerkwithaHeartofGold James]].]]
** Thomas [[DriventoSuicide thinking he should be scrapped]] after spending the whole day messing up is very depressing.
--->'''Thomas:''' No Theo. I'm not being scrapped. But...(sigh) I probably should be. I lost James' cars, and I got trapped in the steelworks, and I want to go home to Sodor, but I don't know the way. [[DespairEventHorizon I'm a useless engine]]. I just do everything wrong.
* "[[https://www.youtube.com/watch?v=vRDBFbr09K4 The Island Song]]" could make some nostalgic and long-time fans tear up.
* On January 2nd, 2017, Ben Forster, who played Mr. Perkins, died of cancer.
** On January 27, 2017, John Hurt, who portrayed Sailor John in ''Sodor's Legend of the Lost Treasure'', died of cancer.
* Creator/GeorgeCarlin, the second narrator in the US, died of heart failure on June 22, 2008.
** In the same year, on May 16th, David Mitton, the original director of Thomas The Tank Engine also died of heart failure.
* The verdict of [[http://thomasfriendsreviews.blogspot.co.uk/2012/05/s15-ep-17-wonky-whistle.html this review]] of [[http://tvtropes.org/pmwiki/pmwiki.php/Recap/ThomasTheTankEngineS15E17WonkyWhistle Wonky Whistle]]:
--> Why, why was this episode known to existence? Why did it get a DVD release on 'Up Up and Away'? Why on this earth did this get approved? Seriously what has this writer done to the great blue engine that we known and loved since the beginning as an air headed dimwit that children are to be looking up too? So many unanswered questions. There are so many flaws in this episode, why did Thomas just puff away with workmen on his boiler? They can seriously get hurt or worse! And puffing away with one vent with animals with the lock unlocked, the animals can get seriously hurt. If Thomas is to teach kids, then what is the moral of this episode? This episode could be more realistic, if its like 'Near Miss' from the 1991 annual, 'Old Iron' and 'The Runaway' put together and instead of a 'wonky' whistle, Thomas' whistle is not their and you have an episode called 'Whistling Runaways', which I wrote on my DA page late last year. All I know is that, this is a rarity for me as this episode is my most hated, I didn't even bother watching the episode. It should be deleted from the entire Thomas series and its history as this is the worst Thomas episode ever made. I honestly feel bad for Greg Tiernan for his wonderful animation being wasted away due to this episode's writing.
* The show is '''leaving PBS for good''' [[https://www.facebook.com/unctv/videos/10159512830105164/ in 2018]]. If you count ''Shining Time Station'''s run on the channel, ''Thomas the Tank Engine'' has been airing on PBS since 1989. It's just heartbreaking to see a long-running staple of PBS disappear.