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Tear Jerker / Sesame Street

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Sure, it does teach you the basics like letters and numbers, but it's never afraid to be touchy, even if it kills them.
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  • We of course start with the most iconic tear jerker of them all. On December 7, 1982, Wil Lee, known for his 13 years as kindly shopkeeper Mr. Hooper, died of a heart attact at the age of 74. There were intially plans to possibly recast him and act like nothing happened. But knowing that it would be a disservice to the children watching, the choice was instead made to tackle Lee's passing head on, and teach that death is a part of life, with Big Bird acting as the children's surrogate. Here's the clip.
    • "You're right, Big Bird. It's... It'll never be the same around here without him. But you know something? We can all be very happy that we had the chance to be with him, and to know him... and to love him a lot when he was here."
    • When Big Bird asks why this had to happen and says "Give me one good reason!" and you know that no one can, because there is no good reason. Gordon gives him the only possible answer, which is both realistic and so very sad: "Because. Just because."
    • What made this scene so realistic, touching and emotional was indeed the genuine emotion shown by the adults as they comfort Big Bird in his realization that, indeed, his beloved Mr. Hooper was never coming back. The scene – done in one take and kept intact – showed that even adults (who fully understand the concept of death) cry and feel very sad when someone close to them dies, and that it is OK to cry, sometimes together, when something sad happens.
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    • And unlike some movies and TV shows, there is no Back from the Dead moment. Once Mr. Hooper died, he stayed deceased ... a nod to real life and a way of helping children understand that when someone dies, for instance a beloved grandparent or older neighbor, they don't come back.
    • Pages from the episode's script in the book Sesame Street: A Celebration reveal that none of the adults' tears were scripted – they were envisioned as keeping their composure but maintaining their comforting tone with Big Bird. But as the scene was filmed, the actors genuinely teared up, and that first take was the only one they could use. In a 2006 interview Bob McGrath said they tried to do a second take but they only lasted a minute before they broke down. This turned out for the best, as the genuine show of emotion made the scene more heartfelt and realistic.
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    • The fact that the show has been running so long since Mr. Hooper's death and seen so many changes over the years makes his passing even more tearjerking in hindsight. Mr. Hooper never got to see Maria and Luis get married, never got to see Miles's adoption or Gabi's birth, never got to learn that Snuffy was real, never got to be a grandfather figure to Elmo, Zoe, Baby Bear, Rosita, Abby Cadabby or Julia and none of them ever got to know him ... again, a nod to real life.
  • Add to that Big Bird singing "It's Not Easy Being Green" to a recently deceased Jim Henson during Henson's funeral service, and the Muppets win at bringing even the most hard-hearted hannahs to tears every time. You can hear Carol Spinney's voice cracking and trying to keep composure throughout the number. The big gut-wrencher is right after he finishes...
    Big Bird: Thank you, Kermit.
    • That song is brought up in this Something Positive that's somehow both funny and sad.
    • Worse yet, Robin keeping the other Muppets together by singing "Just One Person" during the tribute the Muppets did as their first show after his death. Kermit walking through the door at the end is by far the most poignant moment in that scene.
      • Even worse is when, after spending most of the show trying to figure out who Jim Henson was and planning the big production number, Fozzie and the cast find out that Jim Henson is dead while reading fanmail from actual fans. Quite reflective of how one often admires the work but remains unaware of the man behind the work too late.
        Fozzie: *reading letter* "I feel very sorry to hear that your best friend Jim died- *silence hits* ...Wha-...died?
        Gonzo: ...Jim died? But we were just starting to get to know him!
      • Not to mention two years later, Richard Hunt followed Henson to the grave which makes this scene more heartwenching.
        Scooter: Reading a fanmail Perhaps the substance of Jim Henson's genius was the ability to see wonder far off in crazy directions. And get people to follow him there.
      • When Clifford reads the next one, it makes you realize that he was supposed to become part of the main cast. But Muppets Tonight was a failure, and with Kevin Clash resigned...
        Clifford: Dear Kermit, I hope you feel better. I will miss Jim Henson too. I hope this letter makes you feel better. I love you. Bridget Kerwin, Peabody, Massachusetts.
      • When Miss Piggy reads the next one, it makes you remember that Frank Oz semi-retired after his best friend died.
        Miss Piggy: Mr. Henson was a very good and talented teacher. He will never be dead in my heart.
      • By the end of the reading, you can hear some of the Muppets sniffing heartbroken (even Statler and Wardolf have nothing callous to say) and eventually Fozzie snaps in anguish to call off the show because he feels they couldn't do a great guy like Jim enough respect with what they have.
  • The scene where Big Bird tells Snuffy that he has to go away, as he has been convinced by his friends that Snuffy doesn't exist... until he starts wiping away Snuffy's tears, and realizes that Snuffy must be real, as he's crying real tears.
    • This scene gets an emotional Call-Back later in Sesame Street Presents: Follow That Bird where two children sneak into the tent where Big Bird is being held prisoner and wonder if he's real. Then they see a tear and remark that he must be real. Muppet magic.
    • After shooting the scene, the puppeteers removed their masks to reveal that they were both actually crying.
  • Some of the songs:
    • While "I Don't Want to Live on the Moon" doesn't have any sad content, it has a bittersweet vibe because of the slow pace and the emotional message about how they don't want to reside in certain weird places due to the fact that they'll miss their friends and familiar places.
    • "It's Not Easy Bein' Green"
    • "This Frog"
    • "What Do I Do When I'm Alone?" has Grover talk about the things that he does while he's by himself. It heads into tearjerker territory when he mentions that sometimes when he's alone, he gets lonely because he has nobody to show what he's doing. Thankfully, it ends on a light note.
      Grover: "And you are here. So I'm not alone. And I'm happy."
    • Darling, our marriage is doomed. Here stands your heartbroken groom... "Don't Walk" is a lesser example, but it still counts.
      • "One Way" as well, due to the scene where the biker doesn't know how to get to his girlfriend's house past the 'One Way' sign and worries that it won't work out between them, though it ends on a heartwarming note with the girlfriend riding on the back of his bike.
      • From the same album as "One Way" (1977's Signs to be exact), "Please Keep Off The Grass". Marilyn Sokol soars on vocals.
    • A more obscure example: "I Think That It Is Wonderful". While it has no sad vocals, it is another slow-paced, emotional song.
    • A lot of the older songs in general can come to be this over time.
    • The film insert/song It's alright to cry (and it certainly is) is another example, due to its powerful message and the fact that sad situations (hurting your knee, your "stomach aching and your heart aching too", being cranky and tired, being sad for no reason, etc).
    • I'm a Earthworm
    • "Feeling Good, Feeling Bad" is a whole rollercoaster of emotions that sometimes goes into this territory. It starts with Ernie singing about how happy he is and Bert interjecting about his various negative emotions: first sadness ("Do I feel bad!"), then anger ("Grr! I feel like getting mad!" and "Me, I'm feeling crosser than a bear."), then apathy ("And I don't care!"). Eventually, Bert cheers up...but Ernie now has Bert's negative emotions. Luckily, after they go through the song again, they're both happy.
    • There's this one song called "All I Can Do Is Cry". About the three little kittens crying because one of them lost her mitten. Enough to make a lot of cat lovers tear up.
      Ginger Cat: "Whatever happened to that mitten? I'm so sad my heart is splitting. Never got a chance to say goodbye."
    • "Willie Wimple" tells a story about a young boy who chops down trees and litters and the disastrous consequences of what would happen if all children cut down trees and littered. They talk about how there'd be no room due to litter everywhere, no rivers (and therefore nowhere for fish to live and nowhere to sail), no submarines or swimming, no plants or bees and nowhere for birds to live.
      Singer: "If every kid did it, can't you see what an empty, ugly, messy, dirty, icky, messy, no-fun world it would be? Yuck!"
    • The song "The Ballad of the Sad Cafe" (released on the CD Elmo's Lowdown Hoedown) is an in-universe example, as it describes a cafe where cowboys and cowgirls let out their sadness. After the song ends, They cheer up and....
      Cowboy: Hey, You know that I had a good cry. I feel better!
      Cowgirl: Me too! I am not sad anymore! I feel happy!
      A Horse: Hey, What do you all want to do?
      A Cow: Let's to the Happy Cow-Lounge!
      Cowgirl: Oh, I love that place!
      Cowboy: Yee-haw! Let's go there! (As they leave the Sad Cafe).
    • Just Take a Look at 15" is a doo-wop type song about a number 15 who feels unnoticed. Apparently, the boy knows all the other teens except her and she thinks "life is mean". She even cries at one point on the hopscotch. You'd think there'd be a happier way to teach numbers.
    • There's one song about being sad, by Little Jerry and the Monotones.
      Jerry: "I'm sad."
      Monotones: "So sad, so sad."
      Jerry: "Oh boy, am I feeling bad!"
      Monotones: "So bad, so bad."
      Jerry: "I wipe the tears from my eye-y-y-y-y-y-y. Want to sit down and cry-y-y!"
    • One song, sang by Olivia, is about how she is awfully sad for no good reason.
      Olivia: "And I'm sad, I'm sad and it's not much fun to be. And though I know this feeling soon will grow, right now, it's bothering me."
    • "Island of Emotion" is about an island with sections for different emotions. The sadness section, Weeping River, has everyone crying.
    • "Brothers And Sisters" can be this for anyone who's an only child.
      • Even if you have siblings, or if you're fine with being an only child and don't find that aspect sad, there's still the lyric "good dogs can go astray, best friends can move away". Especially the dogs part for anyone who owns a dog, is friends with a friend's dog, or is thinking of getting a dog. After all, you can always write to, text, telephone or email a friend who's moved away but if a dog goes astray, you have to resort to searching.
    • "I'm So Blue", sung by Big Bird in Sesame Street Presents: Follow That Bird. Buckets of tears and a definite need for a hug (or, if the viewer is not a hugger, something equivalent), even when watched as an adult. Poor Big Bird! For context, Big Bird was painted blue and put in a cage and the song talks about how lonely and homesick he feels.
    • "I Wish I Had a Friend to Play With" has Bert singing about how lonely he is after Ernie rejects his suggestions. Luckily, Ernie makes it better.
  • The "Gift of the Magi" Plot with Ernie, Bert and Mr. Hooper in Christmas Eve on Sesame Street.
    • Particularly Bert and Ernie voluntarily bartering away their most prized possessions. You can practically see the internal conflict, and these guys are basically just socks with hands inside them! The Muppeteers are geniuses at conveying emotion without words. Fortunately, Mr. Hooper catches onto what's going on.
  • The Here is Your Life segments sometimes have some dramatic moments with a contestant's neighbor/friend. It happened with the Oak Tree (when Marty and Sarah became chairs), Red House (which moved away from the yellow house), Left sneaker becomes a modern sculpture, and the loaf of breads' friend became peanut butter and jelly sandwiches and french toasts.
    Right Sneaker: It was like twin-brother (voice breaksdown) but lost each other.
    Guy Smiley: Well, Get ready, Because we found him.
    Right Sneaker: Oh no! You couldn't have.
    Guy Smiley: Yes, we did. Here he is at the Museum of Contemporary Arts, Formerly a left sneaker and now, THE MODERN SCULPTURE.
  • From 1997, there's ''Things That I Remember'', a tribute to Ernie and Bert's friendship. It's mostly heartwarming, but the tearjerker hits hard when you consider the Reality Subtext behind the lyrics: First, this was one of Jeff Moss' last songs (if not his last period) written for the show before he passed away from cancer on September 24th, 1998. Second, though Steve Whitmire is playing Ernie, all the flashback clips are of Jim's Ernie. To quote one YouTube commenter, "Can you imagine how hard this must have been for Frank Oz to do?"
  • There's a cute little song called "You and You and Me", written by Jeff Moss, about Elmo, Grover and Zoe taking turns going through a door. The comprehensive 2008 book Street Gang by Michael Davis reveals that Moss, who suffered from cancer, wrote that song the day he died. Since he was a commanding presence on the Street since day 1, being behind some of the most famous songs and episodes, he went out with a blaze of glory.
  • The small cartoon with An Aesop about telling the truth. It begins with a small girl named Cookie with purple skin and crazy red hair and her yellow cat Lucy playing baseball. On the third strike, the window breaks and Cookie mopes that it's the "end of her baseball career". This is tear-jerking enough, but then she has an Imagine Spot about what would happen if she lied that Lucy broke the window: "They" (probably her parents and possibly other relations like siblings) would lock Lucy out and she would have to live in the doghouse with Bruno the dog, but wouldn't like it as he doesn't like to share and would bark at her, so she would run away never to be seen by Cookie again. This leads Cookie to tell the truth to her mother in a very emotional way.
    Cookie: "Mommy! A terrible thing happened!"
    Cookie's mom: "What, Cookie? WHAT?!"
    Cookie: "Oh, you're going to be so mad at me. I was playing baseball with Lucy (starts doing cartoony crying) and I threw the ball (covers her eyes while still crying) and the ball went up, and the ball, it went through the window (puts her hands back down) and it broke! (puts her face up against her mother's dress, gently tugs on it with her arm, still crying) And I didn't mean to do it!" (makes high-pitched sobbing noises)
    • But luckily, her mom forgives her and tells her that everyone makes mistakes, and that it's okay to tell the truth.
  • After Cookie Monster eats a batch of cookies that were meant for a party, he has a rather sad nightmare on meeting a giant, talking cookie, given the name "The Monster Cookie". The Monster Cookie is supposedly a personification of the phrase "You are what you eat". As he tells Cookie Monster in his sob story, he used to be a monster, though he had turned into a cookie because he was on a cookie-only diet, and regrets that he never had any healthier foods. After this sad nightmare, Cookie Monster wakes up moaning, "What a dream! Oh, Very sad!" He then approaches a cookie and scolds himself to never eat cookies again, and eats carrots, fish, and bread, and then a cookie afterwards leaving a remark "Well, Maybe sometime a cookie!" The whole sketch is so over-the-top and dependent on the Space Whale Aesop that it's utterly fantastic. Props to Jerry's and Frank's impeccable performances.
    Cookie Monster: What happened next?
    The Monster Cookie: Then me started to break into chocolate chips!
    Cookie Monster: (Gasp) NO!
    The Monster Cookie: Then me brain turned into cream filling!
    Cookie Monster: OH NO!
    The Monster Cookie: Then me leave crumbs, Whenever me walked!
    Cookie Monster: And in other words, You did not exactly picture your health, right?
    The Monster Cookie: Right! And before me knew it, It was too late... (Voice breaks down) Me transformed into a big monster cookie! (sobbing hysterically)
    Cookie Monster: (also sobbing as well) It's a catastrophe!!! WHY?! WHY?!
    *Scence morphs back to Cookie Monster's home*
    Cookie Monster: (As he wakes up) What a dream! Oh, (Voice breaks down) very sad! (As he was going to eat cookie, He puts it down with anger) OH NO! NO! NO! NO! NO! NO! ME NEVER EAT COOKIES EVER AGAIN! NO! From now on, ME EAT CARROTS! Yeah! (Eats carrots) And fish! (eats fish) And whole wheat bread! (Eats bread) And NO! NO COOKIES! SORRY, COOKIE! ME NEVER GONNA EAT YOU EVER.....Say you talking, cookie?.......You crying, cookie? (Hmmm) (Eats a cookie anyways) Well, maybe sometime a cookie!
  • An in-universe example occurs on one of the game show sketches, ''The Crying Game Show''. In this sketch, host Sonny Friendly tells a contestant a sad story; the contestant that cries the hardest wins the game. Ultimately, the grand prize is Sonny Friendly's own teddy bear - causing Friendly to cry the hardest, thus winning the game. The contestants continue to cry after the announcer blurted that there are no consolation prizes.
    Announcer: Today's grand prize is an official Sonny Friendly Teddy Bear! And it goes to Pierre Blue!
    Sonny Friendly: WAIT! MY TEDDY BEAR?!? THAT'S THE GRAND PRIZE?!? BUT, BUT I LOVE MY TEDDY BEAR!!! YOU CAN'T DO THAT!!! (Sobs very hard)
    Announcer: Sonny Friendly, You are the best cryer on The Crying Game Show, You've WON!!!
    Sonny Friendly: WHAT?!? I WIN? YOU MEAN I CAN KEEP MY TEDDY BEAR?!? WOW!!! This is the most happiest day of my life! Thank you very much! Let's give some contestant some consolation prize!
    Announcer: NO!
    Sonny Friendly: What do you mean NO?
    Announcer: There is no Consolation prize!
    Luke Warm: NO CONSOLATION PRIZE?!? (Voice breaks down) That's awful!
    Ida Normer: (Whines) THAT'S NOT FAIR!
    Pierre Blue: (Whines) IT MAKES ME SO SAD!!!
    *All constestants sobbed in failure*
    Sonny Friendly: Well, I guess we all can't be winners, You know! (laughs) Well this is Sonny Friendly saying we will see you again next time on The Crying Game Show. (To his teddy bear) Oh, Teddy! It's to have you back again. (Kisses his teddy bear)
    • In real life, Game Show hosts cannot win prizes.
  • A Two-Headed Monster skit (the first in episode #2228) provides another in-universe example, where they're presented with the letters "S" and "AD". As the letters get put together into the word "SAD", they get all emotional. Like any time Muppet characters on this show cries, it straddles the line between funny and touching.
  • In general, any songs about the moon or space are this, helped by the fact that many of them are ballads.
    • The song "If Moon was Cookie," especially towards the end when Cookie Monster realizes that if he ate the moon, there would be no moonlight, and he couldn't look out his window at the moon ever again. Oh, *sniff.* Coupled with the simple, yet effective, instrumentation of the song and it becomes a thing of beauty. Just give it a listen.
    • "The Moon Shines" can have this effect as well, with the beautiful arrangement combined with the slightly Deranged Animation and Jerry Nelson singing in his kid voice.
  • The trope name is mentioned vertabrim by Alistair Cookie when the Monsterpiece Theatre parody of 12 Angry Men starts with a Fake-Out Opening sketch-within-a-sketch called Three Sad Cows, which is about, well, three sad cows.
    Alistair Cookie: CUT!!! Me very sorry. That wasn't Twelve Angry Men, That was Three Sad Cows. Story of three cows who are very sad. What a barnyard tearjerker.
  • The moment when Luis and Maria failed to fix Slimey's busted tuba made slimy very sad and Telly sadly blurted that Slimy will not be able to play at The Worm World Music Festival. It was so heartbroken until Telly's struck his head and gets an idea.
    Telly Monster: WHY DIDN'T I THINK OF THIS BEFORE?!? I have a tuba. Slimey can use my tuba! Slimey, I will meet you at the Music Festival.
  • Much of part 2 of the 2001 hurricane arc is this, especially Big Bird's reaction to his nest being blown away from the Hurricane from the previous episode (quoted below). Anyone that lost something cherished in a similar incident - especially their own homes - can definitely relate. There's a reason why all the street scenes from the hurricane week were compiled to help children cope with hurricanes and other disasters (not to mention several reairings after subsequent high-profile hurricanes).
    Big Bird: (shocked) Oh, Gordon!
    Gordon: Oh no...
    Big Bird: (panicking) My home! My nest! My—my everything!
    Gordon: Big Bird, It's gonna be alright.
    Big Bird: No, it's not!
    Gordon: You're right. You're right, Big Bird. It's not alright. But it will be all right.
    Big Bird: But... but my nest! What happened to my nest?!
    Gordon: Well, the wind was too strong, it just blew it all apart.
    Big Bird: Ohh... (cries)
    Gordon: (comforting Big Bird) It's all right, Big Bird, I'm here with you.
  • The episode (made in the wake of the September 11th attacks) where Elmo becomes traumatized after a fire breaks out at Hooper's Store.
    Alan: It's okay. There's nothing to be afraid of. The chief said that the fire is out.
    Elmo: Elmo doesn't care, Alan! Elmo doesn't want to go back into Hooper's Store ever again!
    • Becomes heartwarming when the adults arrange a meeting with real firefighters who tell Elmo that there's nothing to be afraid of. They dedicated their appearance on the show to a comrade who passed away during the attacks.
  • Though somewhat played for laughs, episode #3626 (consisting of a play called "The Princesses and the Stick") has two princesses (played by Gabi and Rosita), two baseball players (Lexie and Louis), a guy who juggles hats (Carlos), and a fisherman (Telly) all cry (eventually all together) because they can't find the single stick that was used to solve their problem before.
    • And if that wasn't enough, the narrator (Celina) starts to get emotional when she goes further into the sad parts of the story.
  • Taking a nod from Mr. Hooper's death, there is a special that dealt with Elmo dealing with the death of his Uncle Jack, from Elmo's father remembering the good times he had with his brother when they were kids to cousin Jesse facing the fact that her father is gone for good. The special, entitled When Families Grieve, part of the Talk, Listen, Connect series for military families — meaning Jack was likely killed in action overseas — was nominated for a primetime Emmy, but lost to the only other nominee, a Nick News special about cancer.
  • The show has a resource kit for families with incarcerated parents. There's a little cartoon film about a girl and her family going to visit her father in prison. It might be the saddest thing in Sesame Street history. Well, one of them anyway.
    It's hard not to be able to touch or hug each other, but Daddy blows me a kiss. I tell him I'll save it for later. Before we know it, it's time to go already. I wish my father can come with us. But this place is where he has to be. Because he violated the law.
  • This animated skit features Noodles the animated Funny Animal cat breaking his owner Nedd's toy plane (specifically, one of the wings fell off). At one point, he has this thought bubble where he's carrying the wing in a bag while wearing a cap and looking dejected. This could be interpreted as either him considering running away from home and taking the wing with him or him considering the possibility of having to take the wing with him to school and feeling guilty about having broken it. Either way, it's tearjerking. Doesn't help that that skit was written by John R. Dilworth, who reportedly was a bit morbid and made his skits slightly Darker and Edgier than standard Sesame Street.
  • On the street scene for episode 2402, the Two-Headed Monster's sobbing in failure at being unable to stop Irvine the grouch's tantrum (which had disrupted the former's lullaby on violin). Maria had said that a grouch baby isn't like a regular baby - Irvine always has a tendency to scream and cry a lot. The whole thing positions itself headlong into Narm Charm. Especially when coupled with Maria's comment on this situation:
    Maria: (To Irvine, who gets more upset), No! Stop it, Irvine. (To the Two-Headed Monster, who ends up sobbing in failure) Oh no! Not you too! (To the viewers) Oh no! And now I have got three people crying... or is it two?
  • One of the Ernie and Bert skits features Bert feeling sad out-of-the-blue and to Ernie's confusion. He then proceeds to list the things that make him sad. Bert feels better, but Ernie doesn't by the end of it (First scene on episode #2621).
    • The old sketch where Bert reminds Ernie that he's special can have this effect as well.
  • The episode where Big Bird's Transatlantic Equivalent Abelardo comes to visit and they both end up losing each other. They then both sing a song, without realizing they're together.
  • Christopher Reeve appeared in The '90s to talk about his wheelchair. Never has a celebrity's "Sesame Street" Cred been so uniquely moving.
  • Similarly, Itzhak Perlman's appearance is another guest segment worth putting on this page.
  • Ray Charles singing his own arrangement of the show's classic "Bein' Green" (from his 1975 album Renaissance) on the show.
  • It's kind of hard to watch Murray host newer Sesame Street Newsflash segments, because the first thing that pops into one's head is "I miss Kermit!" It just drives home how much Kermit's role has diminished over the years, and the contrast to how prominent he used to be.
  • The 2013 episode where the Count wins an award but isn't able to attend the ceremony becomes this when you realize what sparked it (see the Meta tab).
  • Two of the last tracks on the Greatest Hits Album Platinum All Time Favorites fit this trope (even if they're rarely sung nowadaysnote ): "Little Things" sung by Prairie Dawn (one of the last songs by the show's MVP composer Joe Raposo before he died of cancer in 1989note ), and "We Are All Earthlings", an affirmation that we all share this beautiful planet. They're a bit syrupy, sure, but that's what makes them so enjoyable.
    • The 2003 compilation Songs From The Street 35 Years Of Music ends with a remix of the main theme that interpolates samples of some of the show's older albums, showing how far the show has come since then.
  • The moment with a new Muppet character named Alex. Talking about many fathers made him very upset since his father violated the law and has to go to jail for life. They explained that incarceration. He was not the only person who had his father sent to jail. Sofia had to go through her life when her father was sent to jail. This was part of the Little Kids, Big Challenge moment on Sesame Street.
  • A cartoon insert about a little girl figuring out why is the puppy so sad. Well, The two thoughts were bad, but her last thought was that a big bulldog steals the little puppy a bone. And she went "OH MY!" and gives that puppy a bone. And it made the puppy feel better.
  • The book "It's Not Fair!" has a particularly sad part near the end — upon seeing Ernie get all the credit for their lemonade stand, Bert snaps and angrily starts ranting about how HE did all the work and nobody even thanks him for it...before running off in tears, making everyone feel guilty, especially Ernie. Happily, there's a Heartwarming Moment when Ernie uses the money earned from the lemonade to buy Bert a present to cheer him up.
  • Elmo rarely cries, but when he does, it's almost heartbreaking and you can't help but feel sorry for him.
    • In episode #3430, when Elmo is pretending to be sad in a game he calls the "Crying Game". This is actually funny, but it turns sad when Elmo actually does become sad.
    • The entirety of episode #3587 is this, with Elmo being sad for the majority of the episode, especially when he doesn't respond to tickling. Even worse that the reason he's sad is because his fish (not Dorothy, another one called Bubbles) died.
    • The song, “Elmo Didn’t Mean To” from Episode 4302 when Elmo feels guilty for how badly he treated Abby and Telly during a game. This is sadder, since this was one of Kevin’s last performances as Elmo prior to his resignation.
    • One episode has Elmo sad when the adults are too busy to tell him a story, but thankfully it only lasts a few moments. There's also his story ending on the Royal Elmo being tired and too busy to play, but that's just something he made up.
  • When Curly Bear is born, Baby Bear vents his sorrows over the changes in his life to Telly. As you can imagine with Baby Bear being a bit of a Large Ham when he's sad, this was pretty tearjerking.
  • "Sesame Street Home Video Visits the Hospital" has Big Bird get sick and have to spend several days in the hospital. His I-wish-I-wasn't-sick moments can be very tearjerking, especially the scene where he cries after getting a shot and asks "What did I do wrong to get sick?"
  • The one where Gabby gets sick on her birthday. Enough said.
    Nearly everybody: "It's okay to be sad if you're sick on your birthday."
  • Big Bird getting bullied about being too big, too yellow, and sounding too funny to be in the "Good" Birds Club. The saddest part is that each reprise of his originally happy song is sadder.
  • In one of the episodes, everyone: (Oscar, his pets, Elmo, Telly, the kids, Maria...) miss Slimey the worm who's on the moon. They're so sad that it's hard not to feel sorry for them.
  • The Julia episodes can hit a little close to home for anyone who is on the autism spectrum and was ever given a hard time because of it.
  • One episode has Telly chasing a penguin that stole his Triangle Guy costume. He gets so angry that he wants to hit the penguin and Gina asks him to think on what might happen if he tries that idea. What follows is an Imagine Spot where the penguin gets hurt and Telly goes to jail for hitting it. By the end Telly is horrified by what his temper could have made him do.
  • One animated skit featured a mouse singing a song about four cats having different emotions, two of them being sad (which makes the mouse sad too) and angry.
  • In "Elmo Saves Christmas", Elmo wishes it was Christmas every day. When they travel in time to the next "real Christmas", they find out that nobody likes Christmas anymore and it's all dystopian. Some highlights (lowlights?) include the Count being bored of counting the days (and seeming apathetic in general), Big Bird is crying because he hasn't seen Snuffy (who was staying with his grandmother in Cincinnati) all year and the carol singers have lost their voices. Thankfully, thanks to time-travel, it gets resolved.
    • Also sad ([and scary) is the scene where Elmo innocently asks Maria why she's upset because "Christmas is fun". She, in a voice that clearly hints at a breakdown, snaps that she's sick of having fun and wants to actually do her job, only to mix up what kind of appliance she's picked up and bemoan that catching up will be impossible.
  • In episode that shows Maria and Luis's wedding, the song "Wedding Pictures" expresses everyone's private thoughts during the ceremony. It's mostly a blend of heartwarming and funny, but there are two tearjerking moments. One is Maria's mother singing "I wish her father could have lived to see this day." The other is David, Maria's ex-boyfriend, singing about how strange it feels to think of her as someone else's wife.
    • The Reality Subtext of David's verse makes it even worse, as his actor, Northern Calloway, left the show soon afterward due to struggles with mental illness and died just a few years later, right around the same time Joe Raposo and Jim Henson both died. In fact his increasing mental instability was partly why the writers quietly ended David and Maria's relationship and married her off to Luis instead – that and the fact that they wanted to avoid the controversy of an interracial marriage, which is depressing in its own right.
  • The reprise of "Ni Hao" in "Big Bird in China" when Big Bird almost loses hope on his search of the Phoenix. If that wasn't sad enough, the song ends with him shedding a Single Tear (which later gets a callback in Follow That Bird).
    Xiao Foo: (thinking) Even if we didn't find the Phoenix, I'm glad we came. At least Big Bird got to see some of my beautiful land. Oh China, could there be a valley like this anywhere else in the world...?
  • The Big Sad Wolf skit. Little Red Riding Hood does the "Granny, what big ears you have" lines to a wolf except she's got the wrong address and has accidentally visited a nice wolf named Lester with a fragile ego. When she calls him granny and says he has big extremities, he bursts into tears because he thinks she's being mean. The misunderstanding gets cleared up, but Lester cries again when Prairie Dawn mistakes him for the real Big Bad Wolf.
  • In episode #3512, Zoe really wanted to slide down the Finders Keepers pole, but Ruthie refuses because it's dangerous for a little monster like her, even after getting monkey lessons from Joey and Davey, Zoe still gets a no and eventually tells the truth about what's she's been doing.
    Zoe: (upset) But Ruthie, I've worked so hard to be a monkey. I tried and tried and finally I got it and-and, the whole reason I wanted to be a monkey was so I could slide down the pole! (cries in guilt into Ruthie's arms) I'm so sad!
    • Similarly, in a later episode, Zoe cried out loud because she forgot her teddy bear and she can't go to sleep without it, that is, until Sloppy saves the day by letting her share her tiny teddy bear.
  • In The Magical Wand Chase, Onyi tells Elmo, Abby, and Rosita that Sesame Street is only a few blocks away and they're able to get home. But Abby's wand is still missing. Abby feels bad, since she thinks that the events of the special were her fault because of her wand.
  • In this video, the Count falls over after getting dizzy watching the spokes on Olivia's bike spin around. He's fine and just needs a bandage from the fall, but then Big Bird accidentally bites his finger. He decides to stand still and not count (because both accidents happened while he was counting) but then a bee lands on him and stings him for no reason. He is then very sad.
    Count: "Oh, dear! I will not count the one exquisitely painful bee sting on my fingertip. But perhaps, before I go home to bed, I will count this one... this one... one excruciating scream of pain! (most pitiful scream that you can imagine) (sighs in relief) Yes, I feel better already."
  • Karli, a recent Muppet introduced to educate about foster care (it's all but said later on her mother is struggling with addiction), invites Elmo over for pizza, and they make placemats together with her "for-now" parents. When she can't find her placemat (later revealed to be hidden under the pizza box), Karli starts crying, saying she doesn't "have a place". Poor girl...
  • Until 2019, only two people were on the show from episode one: Bob Mcgrath and Carroll Spinney. The characters, and the Muppets, may live on forever. But the people do not, and after fifty years of his Big Bird being a presence in countless fans' lives across many generations, the end of an age was marked with Carroll's retirement.

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