Barenaked Ladies/Tear Jerker

This Canadian alternative rock band has a lot of tear-triggering songs.

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• "Tonight is the Night I Fell Asleep at the Wheel", which plays a tune that sounds like it belongs on a cheerful carnival calliope, but whose lyrics tell the story of a car crash and the futile attempts to save the titular driver whose love is the "last thing on my mind". The narrator? Ed Robertson's brother, who died in a motorcycle accident.
  • In the same vein, "Am I The Only One" and "Leave". The former was originally going to be about Ed's (at the time) fiancée, but changed.
• "War On Drugs" being another big one.

"She likes to sleep with the radio on
So she can dream of her favourite song
The one that no one has ever sung
Since she was small"

• "Celebrity" is somewhat of a downer, too. The narrator talks about his goal in life, and then (presumably) achieves it and realizes how horribly hollow being a celebrity is.
• Then there is "What A Good Boy".
• For a song about a window washer who's afraid of heights, "When I Fall" does a great job at cuing the waterworks.

"I look straight in the mirror
Watch it come clearer
I look like a painter
Behind all the grease
But painting's creating
And I'm just erasing
Chrystal clear canvas
Is my masterpiece.

• Common consensus on singing along to "Break Your Heart" is impossible because of two things.
  • The Incredibly Long Note
  • The inevitable tears.