Some people suggest that citizens should “pay taxes with a smile,” knowing that the citizens have patriotically performed a civic duty. Many taxpayers, however, do not enjoy paying taxes. The saying “pay taxes with a smile” was not meant to be taken literally.
 
The “pay your taxes with a smile” joke has been cited in print since at least 1914:
 
“Optimist—Be a hero and always pay your taxes with a smile.
Taxpayer—I would like to, but they don’t accept them. They insist upon money.”
 
The joke appeared in many newspapers in the 1930s and is included in several collections of sayings about taxes.
   
“Hi, I’d like to buy a cookie with chocolate chips.”/“Sorry, we only accept cash,” “I tried to buy a hot dog with ketchup, but the vendor would only accept cash,” “I went to a deli and said, ‘I’d like to buy a bagel with cream cheese…‘“ and “I’d like to buy a ham and cheese baguette with pickles.”/“Sorry, we only take cash or card” are similar jokes.
   
   
24 June 1910, Bridgeton (NJ) Evening News, pg. 2, col. 2:
IF YOU wish to endear yourself to the heart of the tax collector, pay your taxes with a smile, and tell him that you are glad to pay him, even though you have to lie a little.
 
16 April 1914, Correctionville (IA) News, pg. 7, col. 7:
Only Too Willing.
Optimist—Be a hero and always pay your taxes with a smile.
Taxpayer—I would like to, but they don’t accept them. They insist upon money.
 
23 December 1933, Moorhead (MN) Daily News, pg. 2, col. 1:
“Pay your taxes with a smile,” advises a patriotic pamphlet. Everybody would be glad to do that if smiles were acceptable at the county treasurer’s office.
 
29 November 1934, Alvord (IA) Register, “On the Funny Side,” pg. ?, col. 4:
Cash Wanted.
“Pay your taxes with a smile,” advised Mrs. Gotrocks.
“I should love to,” said Miss Comely, “but they insist on cash.”
 
Google News Archive
19 March 1937, Chehalis (WA) Bee-Nugget, “Comment,” pg. 8, col. 3:
It is tax time, and we have been advised by optimistic writers to pay the taxes with a smile. But we have never found an official who will write a receipt for a tax paid with a smile.
 
21 January 1944, Marietta (GA) Daily Journal, pg. 6, col. 1:
It’s very fine to pay your taxes with a smile but you will find it necessary to accompany it with some cash.
 
Google News Archive
21 February 1946, Deer Park (WA) Union, “Cracks…In The Cement” by Minnie Olson, pg. 3, col. 6:
Some one has said that we should pay our taxes with a smile, but we always found that the tux collector wanted money and lots of it.
 
Google News Archive
3 December 1957, Gettysburg (PA) Times, pg. 1, right masthead:
GOOD EVENING
Then there was the fellow who tried to pay his taxes with a smile—but they wanted cash.
 
14 February 1961, State-Times and Morning Advocate (Baton Rouge, LA), “Little Liz” syndicated comic strip, pg. 11-B, col. 4:
Any good citizen would be glad to pay his taxes with a smile—but the government prefers cash.

5 January 1966, The Oregonian (Portland, OR), “Soaper Says…,” pg. 22, col. 2:
The government, on any level, would naturally prefer for us to pay our taxes with a smile. But even with a cuss-word, they’ll take the money anyway.
 
Google Books
The Don’t Sweat Guide to Taxes:
Avoiding Stress Over April 15th
By Richard Carlson
New York, NY: Hyperion
2002
Pg. 16:
There is an old joke about the fellow who tried to pay his taxes with a smile… but they wanted cash!
 
Google Books
As Certain As Death:
Quotations About Taxes
By Jeffrey L. Yablon
Arlington, VA: Tax Analysts
2010
Pg. 191:
It would be nice if we could all pay our taxes with a smile, but normally cash is required. — Anonymous
     
The Dirty Dozen’s Bunker
10 Bears
08-13-2011, 06:04 PM
I still catch reruns, on occasion!
“I tried to pay my taxes with a smile, but they insisted on MONEY!”
(Commenting on a YouTube video punchline in “Hee Haw Pickin & Grinnin”—ed.)