I was amused when reading this Wikipedia article about early rock'n'roller Conway Twitty. He tried to found a chain of burger restaurants called "Twitty Burger", but it failed and he tried to pay back his initial investors while deducting those payments from profits. The IRS were not impressed, but ultimately Twitty won his case. Some poetry went back and forth during the case.. as follows:

In the case Harold L. Jenkins (a/k/a Howard Twitty) v. Commissioner, 47 T.C.M. (CCH) 238 n.14, Twitty sued to allow his repayment of investors in his bankrupted Twitty Burger fast food chain to be deductible as a business expense. The opinion closed with the following poem:

Twitty Burger went belly up
But Conway remained true
He repaid his investors, one and all
It was the moral thing to do.
'His fans would not have liked it
It could have hurt his fame
Had any investors sued him
Like Merle Haggard or Sonny James.
'When it was time to file taxes
Conway thought what he would do
Was deduct those payments as a business expense
Under section one-sixty-two.
'In order to allow these deductions
Goes the argument of the Commissioner
The payments must be ordinary and necessary
To a business of the petitioner.
'Had Conway not repaid the investors
His career would have been under cloud,
Under the unique facts of this case
Held: The deductions are allowed.

The IRS responded by allowing the judgment to stand while implying that if a similar case arose in the future their opinion would differ:

Harold Jenkins and Conway Twitty
They are both the same
But one was born
The other achieved fame.
The man is talented
And has many a friend
They opened a restaurant
His name he did lend.
They are two different things
Making burgers and song
The business went sour
It didn't take long.
He repaid his friends
Why did he act
Was it business or friendship
Which is fact?
Business the court held
It's deductible they feel
We disagree with the answer
But let's not appeal.

Source: Wikipedia. Licensed under the GFDL.