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Tear Jerker / Alvin and the Chipmunks

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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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The 2007 film

  • 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.
    Alvin: 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...
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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.
    (She leaves as the auditorium's lights go out on Alvin.)
  • Not to mention, when Alvin arrives home, his brothers pretend to be asleep and ignore him.
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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 as his eyes well up with tears, slumping 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. The song she's singing doesn't help either.
    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 5; 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. (Tears form in his eyes. 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, angrily 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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