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Tear Jerker / Alvin and the Chipmunks

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For The Alvin Show:

A Chipmunk Christmas

  • Alvin gives away his prized Golden Echo Harmonica to a local kid, Tommy, after learning he's very ill in hopes that it makes him fell better. However, Alvin doesn't want to tell Dave as he is the one who bought the harmonica for him originally and Alvin worries that Dave would be heartbroken to learn he gave it away. When the Chipmunks learn that they've been asked to do a Christmas Eve concert at Carnegie Hall and they've requested Alvin to do a solo on his harmonica, Alvin quickly tries to raise money to buy a replacement. Naturally Dave takes notice of this and wonders what the three are up to, causing them to accidentally state that Alvin's buying a present for himself. Dave mistakenly thinks the three are only thinking of themselves, and believing they've lost sight of the Christmas spirit, when it couldn't be further from the truth. Unlike the usual over the top "ALVIIIN!" rages Dave goes into, the following exchange between him and Alvin is horribly somber, made worse from the fact that it's from a terrible misunderstanding.
    Alvin: ...Are you still mad at me?
    Dave: No. I'm just very disappointed.
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For Alvin and the Chipmunks/The Chipmunks

https://static.tvtropes.org/pmwiki/pub/images/the_chipmunks_grieve.png
You'd cry too knowing what the Chipmunks had gone through here...
  • The episode "Cookie Chomper III". Oh God, easily the biggest tear jerker of the show. An adorable stray kitten sneaks through a window into the house and the chipmunks adopt him. Dave even overcomes his allergy to cats and accepts the new pet. One night, the kitten wanders out through an open window in the chipmunks' bedroom and is hit by a car. It's extremely HEARTBREAKING seeing how realistically the Chipmunks reacted to this situation. Theodore is incredibly upset (to the point where he's in denial of Cookie's death), Simon is too miserable to do anything, even Alvin is saddened by the whole thing, going as far as removing the live plants from the house so the family doesn't have to deal with any more death. He even yells at their neighbor for walking her dog across their house, saying that he won't allow any living beings here. The neighbor and the dog look confused and upset upon hearing this.
    • The driver's reaction is heartbreaking as well, before Dave breaks the news of Cookie's death to the chipmunks. The driver quietly knocks on the Sevilles' door and is seen holding Cookie's collar. He constantly apologizes for running over their kitten.
    The Driver: I'm sorry, I uh.. I have some bad news. I tried to stop my car in time, but the kitten was in the street, but I'm sorry.
    Dave: Thank you, for telling me. (sadly shuts the door)
    • Later on, the Chipmunks talk together about Cookie's death and each one blames himself for letting Cookie get out. To top it all off, the fact that in this scene it's ALVIN... the one Chipmunk that is usually a troublemaker and thinks he is the greatest... actually CRYING over losing the poor kitten, can easily cause your eyes to water up.
    Alvin: It’s all my fault! (bawls his eyes out)
    • It doesn't get any easier when Dave helps his boys come to terms with the loss by helping them to memorialize their beloved pet, buying a special plaque upon which the kitten's collar will hang in his memory. The accompanying montage and especially the music playing over the entire scene will certainly have you choking up before its over.
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    • Additionally, the episode was based off a real-life experience, when Ross Bagdasarian Jr. and his wife Janice Karman's dog Tiger Lily was killed by a car. The Chipmunks' new puppy Lily was named after her.
  • The Chipettes' origin story episode, especially when Eva steals Olivia’s bracelet, Olivia is forced to clean the bathroom, the Chipettes are nearly captured by Ms. Grudge and put in the singing orphans group, and the Chipettes (especially Jeanette) worrying that they’ll never see Olivia again. The fact that the Chipettes were homeless for EIGHT YEARS before finally coming to Los Angeles is a real kick in the gut.
    • Also when the Chipettes become Miss Miller's adoptive daughters in “Help Wanted Mommy”. For context, the school finds out that the Chipettes are orphans and threatens them with expulsion, since it’s against school policy for the students to not have guardians. The Chipmunks eventually ask Miss Miller to take care of the girls. While they don’t get along at first, she eventually comes to love them when she discovers that they love music as much as she does.
  • The Chipmunks meeting up with Vinny, their Missing Mom in the special "A Chipmunk Reunion".
    • Other tearjerkers of the special include Vinny explaining that she really wanted to keep them but truly had no choice, Alvin trying to tell her that he felt her absence the most and then running away with his brothers on tow, the Chipmunks being attacked by a wild boar and, after Vinny saves them, thinking she's dead.
  • The episode "Sploosh" may tug on a few heartstrings, particular those who ship Simon and Jeanette.
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    • Trusty (Simon) finding a sickly Princess Montana (Jeanette) in a tank and begging Buford Bubbles (Alvin) to let her go.
    Simon: Can’t you see she’s dying?! Have a heart!
    • Trusty meeting Montana for the first time. She is very clearly frightened.
  • The It's a Wonderful Plot episode "Dave's Wonderful Life" which has a stressed Dave suffering from financial problems, as his recent songs were rejected. It's hard not to feel bad for him when he laments over his problems before going to bed.
    • Also, the fates of the three Chipmunks without Dave: Simon is still in kindergarten at the age of 40 because he failed in a spelling bee contest and lost his self-confidence, Theodore becomes a hermit, and Alvin is struggling in a dead-end job.
  • In “Whatever Happened To Dave Seville?”, Dave gets a wax statue of himself. However, the Chipmunks think that Dave has “zomboidrigidosis” and don’t realize they’re talking to his statue. You can imagine how devastated Alvin was when he put the statue in the sun and it started melting.
    Alvin: Look how loose his skin is!
  • “The Chipmunks Story”: The baby brothers are left on Dave’s doorstep by Vinny. Dave takes them in, but is threatened with eviction from his landlord, who hates animals. Later, Dave’s girlfriend Julie breaks up with him because she’s afraid of the Chipmunks. Adult Fear kicks in when Dave finds out that the landlord tried to feed the boys to a snake. Also, Dave is in danger of being fired from his songwriting job. Luckily, Alvin convinces Dave’s boss to triple his salary.
  • “Merry Christmas, Mr. Carroll”: Alvin is on his paper route and delivers a newspaper to his grouchy neighbor Mr. Carroll, who lives alone with his cat Ebeneezer. However, the newspaper is wet and Mr. Carroll demands a dry one. Angrily, Alvin heads home to finish his homework assignment on the true meaning of Christmas. In a Christmas Carol spoof, the Ghost of Christmas Past (Dave) shows Alvin the Seville’s old house. Since they were so poor, they couldn’t afford to get Dave expensive gifts. However, Dave used his gifts to write “The Chipmunk Song (Christmas Don’t Be Late)”. The Ghost of Christmas Present (Theodore) tells Alvin that since Mr. Carroll never gets visitors, he relies on Alvin to bring him the paper each time, since Alvin is the closest thing to a visitor he’s ever gotten. Finally, the Ghost of Christmas Future (Simon) shows Alvin what will happen if he doesn’t change his ways. Alvin is a greedy slob who eats so much Christmas dinner that he gains a Balloon Belly and accidentally injures his grandparents. Grandma and Grandpa Seville’s injuries won’t heal until around May. An uncaring Alvin just demands gifts and jumps around, his weight causing the house to collapse and kill everyone. Horrified, Present!Alvin begs Ghost!Simon for another chance, only for him to wake up to his unfinished homework. With a complete change of heart, Alvin discovers the true meaning of Christmas and Mr. Carroll is once again happy.
  • In “Good Old Simon”, Simon is sad about being ignored and runs away from home. Imagine what would happen if his brothers never found him. The music does NOT help.
  • Anyone who’s ever had surgery might feel unease at “Operation Theodore”, especially since Brittany unintentionally put Theodore in danger (he’s fine, but it’s still unsettling). Also, Bobby crying about his upcoming tonsillectomy is certainly understandable.
  • Brittany getting sick in “Hearts and Flowers”. The poor girl was only trying to create a diversion but she wasn’t found in time.
  • “The Legend of Sleeping Brittany”. Brittany could have been in a coma indefinitely if Alvin hadn’t saved the day.
  • “Miss Miller’s Big Gamble” tackles the issue of gambling addiction. The Millers nearly lose their house.
  • In “Lights Camera Alvin”, notorious chipmunk con artist Harry has Alvin act in a movie- without his brothers. Alvin is lonely and homesick, and the montages of him helping his brothers certainly tug on the ol’ heartstrings.
  • Simon crying about the Lucy the fish escaping in “Gone Fishin’”. Also, the fact that the marine park is based on Sea World hits way too close to home, since the topic of animal abuse is brought up.
  • In “Court Action”, Theodore gets severe anxiety from being the judge and starves himself to the point of fainting. You can’t help but feel bad for the poor kid.
  • In “Angelic Alvin”, an old man misses the bus and breaks down in tears. Simon gets the driver to go back and says “he might not have much longer to live”.
  • In “Alvin, Alvin, Alvin!”, Alvin becomes severely depressed and goes through an identity crisis. Keep in mind that this kid is EIGHT. Anyone suffering from depression, dissociation, and/or loss will definitely relate.
  • “A Special Kind Of Champion” has Alvin coaching a kid named Louie. Louie has cerebral palsy and is in a leg brace. Alvin is at first reluctant to coach a disabled person, which brings forth the very real and heartbreaking topic of ableism.
  • “Mind Over Matterhorn” has a depressed Brittany about to jump into a pool, with Alvin thinking she was going to commit suicide. Later, the kids get trapped in an avalanche. Dave’s Adult Fear is certainly understandable.
  • “Theodore’s Life As A Dog” has a scene where Alvin is dressed in a dog costume and a stray dog shows up, with Alvin thinking that Theodore turned into a dog. The dog and Alvin are taken to the pound. If Alvin hadn’t called home, he would have probably been locked up for a long time and possibly euthanized.
  • Brittany’s Imagine Spot in “Cinderella Cinderella” where Miss Miller cruelly refuses to let her go to the ball and she breaks down crying.
  • The boys getting trapped in the Fitzgerald mansion in “When The Chips Are Down”. Sad music plays as they break their way out.
  • In “Mother’s Day”, when the boys try to sabotage Dave’s dates, they make it look like Dave abuses them.
  • Dave’s Imagine Spot in “The Incredible Shrinking Dave” ends with him getting separated from the boys as the raft crashes. A sad song then plays.

For The Chipmunk Adventure:

For Alvin and the Chipmunks Meet Frankenstein:

Alvin and the Chipmunks Meet the Wolfman:

For 2007 Alvin and the Chipmunks film with Jason Lee:

  • The Third-Act Misunderstanding when the chipmunks find the goodbye letter Dave had written for them earlier in the movie. Since they find it after he sarcastically suggested that they go live with Ian if he was treating them so much better, they assume he still feels that way and really does want them gone.
    Simon: (Reading the letter with the others) '...You should go back to your real home in the forest.;...I guess he really does want us to go.
  • Later on, when they realize just how unhappy they are working with Ian and want to go home to Dave, but thanks to Ian's manipulation, they're convinced Dave doesn't want them back.
    Theodore: Guys....I wanna go home.
    Simon: What do you mean? You are home.
    Theodore: No, I mean home home. You know, with Dave.
    Alvin: But, Theodore, come on. Wake up and smell the toffee. Dave...doesn't even want us. He doesn't care enough to even come to our show....

For The Squeakquel:

  • When Alvin arrives at the school's talent show sing-off due to being away at a football game, thus giving the Chipettes a victory by default that they are not proud of. When he finally arrives, the gloomy auditorium's empty and Brittany calls him out on his irresponsible and cocky selfishness before leaving.
    Brittany: You know what, Alvin? Ian was right. You don't care about anyone but yourself. (Alvin slumps; As Brittany begins to leave, she turns around) Oh, and by the way, I never wanted to win this way.
    (leaves; the auditorium's lights go out on Alvin)
  • Not to mention, when Alvin arrives home, his brothers pretend to be asleep and ignore him.

For Chipwrecked:

  • Shortly after they build huts on the shore, Alvin's Jerkass Realization and his assumption that he's the reason why they haven't been found by Dave yet. He's choking up Tears of Remorse the entire time.
    Alvin: Brit, I...I think I know why Dave hasn't come.
    Brittany: You do? Why?
    Alvin: 'Cause he's not even looking.
    Brittany: Alvin, why wouldn't he be looking for us?
    Alvin: Because I drive him crazy. You know, the way Simon's been driving me crazy? I mean, that's what I've been doing to Dave. For years. No wonder he hates me. (he sighs in sadness and his eyes grow watery. He slumps on the railing in grief)
  • When Dave eventually finds the chipmunks in the forest just as Alvin is assigning responsibilities. What really sells it most is the extremely guilty and bittersweet look on Alvin's face as he realizes how much of a jerk he has been. On one hand, he's relieved and uplifted to see his beloved father figure again, but still tearfully upset and remorseful about his antics.
  • Jeanette getting kidnapped by Zoe and then forced to bring her the treasure. Jeanette's singing doesn't help.
    Jeanette: S.O.S. Please, someone help me. It's not healthy for me to feel this...

For Road Chip:

  • When the Chipmunks and Miles are going to sleep outside by a tree next to the freeway, Miles reveals that his dad didn't die when he was only 7, he abandoned him. He then bitterly remarks that he suspects the sweet man that is Dave, will probably abandon them too. An example of Fridge Sadness; Miles was so hurt by his father, that he can't trust a father figure again, no matter how nice he seems.
    • after this reveal, Miles jerkishly lies that he just doesn't care.
    Miles: I've done just fine without him. (eyes grow watery. he looks away from the chipmunks, staring solemnly at the moon)
  • When the chipmunks celebrate successfully averting Dave's "proposal", Miles, who's begun to think of the 3 as his brothers, bursts out in tears, and storms out.
    Miles: I saw you celebrating like you won the Super Bowl...the second you found out we weren't gonna be family. So..see you (puts earbuds in his ears)
  • When Alvin explains the whole reason they left the house to Dave and return the engagement ring to him. Then it turns out Dave was never gonna propose to Samantha at all; the ring the Chipmunks stole was actually for his friend Barry's proposal to Alice. In place of the ring, the box has a breath mint, and Alice storms off, insulted. What sells it most is the extremely guilty look on Alvin's face as he realizes he really screwed up this time.
    • Right afterwards, Dave scolds the Chipmunks in the hotel room.
    Dave: Look, the only reason we're not going back to L.A. right now is 'cause I have to be here. (sighs) I don't think I've ever been more disappointed in you boys than I am right now. (leaves and closes the door behind him)
    Simon: If Dave didn't wanna get rid of us before, he definitely does now.


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