Rare, Obscure, and Weird Songs From the 40s, 50s, and 60s

Tie Me Kangaroo Down, Sport by Rolf Harris
Stranded in the Jungle by The Kadets
May the Bird of Paradise Fly Up Your Nose by Little Jimmy Dickens
(I Caught You With Your) Backfield in Motion by Mel and Tim
Tennessee Bird Walk by Jack & Misty

These were the first that came to mind
 
The kids and I used to listen to a radio program called The Doctor Demento Show. This was back in the early 80s, so not quite in the OP's time-frame, but these 2 songs tick all the Rare, Obscure, and Weird boxes.

Fish Head ~roly-poly fish head
(the song actually starts at 2 minutes 13 seconds..the intro is too long)


Dead Puppies ~aren't much fun

 
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Tie Me Kangaroo Down, Sport by Rolf Harris
Stranded in the Jungle by The Kadets
May the Bird of Paradise Fly Up Your Nose by Little Jimmy Dickens
(I Caught You With Your) Backfield in Motion by Mel and Tim
Tennessee Bird Walk by Jack & Misty

These were the first that came to mind
Your mind seems cluttered lol. Backfield in motion is really strange.
 
Your mind seems cluttered lol. Backfield in motion is really strange.
You don't know the half of it. I was going to post Barefoot in Baltimore, the third single by the Strawberry Alarm Clock, but I thought better of it.
Is it better to have a cluttered mind or an empty one?
 
You don't know the half of it. I was going to post Barefoot in Baltimore, the third single by the Strawberry Alarm Clock, but I thought better of it.
Is it better to have a cluttered mind or an empty one?
I apologize for my cluttered remark, I was trying to be funny but it did not come across right.
Yes its better cluttered than empty.
 
Does it get weirder or more obscure than this? This is an autobiographical song by the one-armed drummer of a Boston area band.

 

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