Funny But Sad

From This Might Be A Wiki

Discussed in Gigantic, songs that are funny, but sad, or songs with depressing lyrics, but cheerful music.

Become A Robot - Upbeat and bouncy with lyrics such as "Hip hip horrific is our thing."
Broke In Two - Seems to have been written with this theme in mind. "You said, 'I'm gonna run you down.' I heard, 'I'm an orangutan.' "
Dark And Metric - "Sesame Street vibe"
Don't Let's Start - "Everybody dies frustrated and sad, and that is beautiful", etc.
Four Of Two - His date never shows up, and yet he still just keeps waiting and waiting and waiting.
Fun Assassin
Hopeless Bleak Despair
I Palindrome I
I'm Having A Heart Attack - the lyrics describe an explosively painful and melancholy event, but Linnell's voice is indifferent and the music is calm and groovy
It's Not My Birthday - The lyrics weave together a number of rainy and depressing ideas which otherwise have little relation (liner notes reveal that even TMBG classed this one as hard to interpret), and are sung to an upbeat and cheery tune for an amusing contrast. It's a notable example.
Lucky Ball & Chain
Mr. Me - "He ended up really, really, really sad" is one of the most gleefully sung lines in the TMBG canon.
My Man - "There is no way to repair the break"
Narrow Your Eyes
No One Knows My Plan
Now Is Strange
Older
Stalk Of Wheat - Sounds like a kids song, but the lyrics are about a guy down on his luck.
They Got Lost
They'll Need A Crane
Twisting