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Tear Jerker / The Chipmunks

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  • The episode "Cookie Chomper III" is 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. But 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, and 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 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, each one tearfully blaming himself for letting Cookie get out, with Alvin being the most remorseful of them all. The fact that the egotistical troublemaker of the bunch is left a sobbing mess while his brothers try to comfort him says a lot about what the Chipmunks had to go through this entire episode. Jesus.
    • 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 it's over.
    • Additionally, the episode was based on a real-life experience, when Ross Bagdasarian Jr. and his wife Janice Karman's dog Tiger Lily was killed by a car. Thus, 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 (who could also double as Nightmare Fuel) 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.
    • 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. 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 is only happy to hear they'll heal in time to go present shopping for his birthday, and jumps around, his weight causing the house to collapse and kill everyone (Could also double as Nightmare Fuel.) 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.
  • “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.
  • "Middle Age-Davey": It's Dave's birthday and he's hit middle age. He finds out his favorite songs are now considered "golden oldies." The cashier refers to him as "sir" and forcibly helps him with carrying his groceries. And someone in the parking lot derisively calls him old. When Dave looks at his reflection in his car mirror, in his mind he sees an ancient old man. Dave says in despair, "I feel 80 years old."

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