Tear Jerker / Jim Croce

• One of Croce's big hits, "Time in a Bottle," feels with heartbreaking eeriness like Croce knew he had little time left. He died in a plane crash a few years later after writing this song.
• "Operator (That's Not the Way It Feels)" is definitely this. It sounds so happy, but the song itself chronicles the latest outing of a man asking the titular operator for the phone number of a girl he loved and his friend, to tell them that he's happy for them and that he got over the heartbreak of her leaving him. He can't in the end, since he just ends up opening old wounds and breaking down into tears. And he explicitly says that he's done this multiple times.
  You can keep the dime.

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