A plaque remaining from the Big Apple Night Club at West 135th Street and Seventh Avenue in Harlem.

Above, a 1934 plaque from the Big Apple Night Club at West 135th Street and Seventh Avenue in Harlem. Discarded as trash in 2006.

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“Is it still considered wine tasting if I’m on my third glass?” (4/24)
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Entry from April 08, 2016
“The reason Uncle Sam has to wear such a tall hat is that he’s always passing it around”

A jocular line about Uncle Sam appeared in Earl Wilson‘s syndicated entertainment column in January 1962:

“‘We wondered,’ said Arnold Glasow, ‘why Uncle Sam wore such a tall hat—till he began passing it around for taxes.’”

Arnold Glasow (1905-1998) contributed many famous one-liners to many publications.


Answers.com
Q: Who is Arnold Glasgow?
A: He was my father-in-law. Arnold Henry Glasow (notice no second g in last name) was born in Fond-du-lac, Wisconsin in 1905, and died in Freeport, IL in 1998 at age 93. He graduated from Ripon College, and started his own business when he moved to Freeport just after the depression. His business was a humor magazine that he marketed to firms nationally, which firms would turn it into their “house organ” to send to their customers. He carried on this business for over 60 years, publishing his first book at age 92. The book is titled, “Glasow’s Gloombusters,” one of the many titles he put on his work during his career. He was cited frequently in the Wall Street Journal, Forbes, the Chicago Tribune and many other major organs. He was a regular contributor to the humor sections of Reader’s Digest. Sixty years of productive work. Many attributions. A real American thinker, self-effacing and generous of spirit, he shunned the national spotlight.

Google News Archive
19 January 1962, Spartanburg (SC) Herald, Earl Wilson entertainment column, pg. 4, col. 5:
WISH I’D SAID THAT: (...) “We wondered,” said Arnold Glasow, “why Uncle Sam worse such a tall hat—till he began passing it around for taxes.”

Google News Archive
4 May 1962, Lakeland (FL) Ledger, “Today’s Chuckle,” pg. 1, col. 4:
We wondered why Uncle Sam wore such a tall hat until he started passing it around for taxes.

Google Groups: comp.robotics.misc
Need help.
Frederick John [MSAI]
4/21/00
(...)
“We often wondered why Uncle Sam wears such a tall hat, until he started passing it around for taxes.”

Google Books
Spending Your Way to the Poorhouse
By Tommy L. Gardner
Bloomington, IN: AuthorHouse
2004
Pg. 188:
We often wondered why Uncle Sam wears such a tall hat, until he started passing it around to collect taxes.

Google Books
The World’s Greatest Wacky One-Line Jokes
By Bob Phillips
Eugene, OR: Harvest House Publishers
2005
Pg. 116:
Uncle Sam
The reason Uncle Sam has to wear such a tall hat is that he is always passing it around.

Google Groups: Dan and Ginny
jokes
danandginny
4/3/10
(...)
I figured out why Uncle Sam wears a tall hat. It comes in handy when he passes it around.

Twitter
Marty Wazbinski
‏@Rumexx
I figured why Uncle Sam wears such a tall hat.  It comes in handy when he passes it around.  ---Soupy Sales
4:34 AM - 2 Mar 2015

Posted by Barry Popik
Other ExpressionsOrigin of "Uncle Sam"/"Brother Jonathan" • Friday, April 08, 2016 • Permalink