“I like to play chess with old men in the park…although it’s hard to find 32 of them”

There is a difference between playing chess against people and playing chess with people (for example, human chess pieces).  American stand-up comedian Emo Philips said in a November 2009 interview:
 
“I like to play chess with old men in the park. Of course, the tough part about playing chess with old men in the park is finding 32 of them willing to stand still for hours on end. The trick is to put the decrepit ones up front.”
 
There are 32 chess pieces, with 16 for each side. Philips’ line quickly became a very popular chess joke.
 
“A computer once beat me at chess, but it was no match for me at kick boxing” is another Emo Philips chess joke.
 
   
Wikipedia: Emo Philips
Emo Philips (born Phil Soltanek; February 7, 1956) is an American comedian. Much of his stand-up comedy makes use of paraprosdokians spoken in a wandering falsetto tone of voice. The confused, childlike delivery of his material produces the intended comic timing in a manner invoking the ‘wisdom of children’ or the idiot savant.
     
Twitter
Josh Finkelstein‏
@jfinklink
loves playing chess with old men in the park… the trick is finding 32 of them
7:41 AM - 28 Oct 2009
 
13 November 2009, Dayton (OH) Daily News, “Talking Emo with Mr. Philips” by Don Thrasher, pg. GO26:
In a world populated with cookie-cutter comedians, Emo Philips’ unique world view has always separated him from the pack. Philips, who performs at Wiley’s Comedy Niteclub through Sunday, Nov. 15, recently shared his thoughts with us on a number of topics.
(...)
Q Performers often have unusual hobbies. What pastime activities of yours might surprise people?
A I like to play chess with old men in the park. Of course, the tough part about playing chess with old men in the park is finding 32 of them willing to stand still for hours on end. The trick is to put the decrepit ones up front.
     
The Guardian (London, UK)
Edinburgh festival 2010
Emo Philips
Pleasance Courtyard, Edinburgh
Brian Logan
Thursday 12 August 2010 11.48 EDT
(...)
It’s his one-liners that he’s famous for, word and mind-bending constructions as flawless as diamonds. “I like to play chess with old men in the park. The hard part is finding 32 of them.”
   
Twitter
Pete Manning‏
@PeteMandingo
Emo Phillips: “I like to play chess with old men in the park. The hard part is finding 32 of them.”
5:22 AM - 13 Aug 2010
 
Secrets of the City
EMO PHILIPS
Posted on September 27, 2011 at 6:03 am
“I like to play chess with old men in the park,” says Emo Philips. And this is what you would expect from a 55-year-old who looks (weird) and sounds (also weird) like Emo Philips does. Then he adds: “The trouble with playing chess with old men in the park is finding 32 of them.” This is the paraprosdokian essence of stand-up comic Emo Philips, whose 30-plus-year stage career has been marked by portraying a weird mixture of Ed Wynn, Pee-wee Herman, and that time Crispin Glover was on Letterman in the ’80s.
 
Chess.com
Stand-Up Chess: Emo Philips
DaveOakRidges
Mar 1, 2012, 8:20 PM
One of the more unusual American stand-up comedians, Emo has contributed the following to chess humour;
(...)
2. Chess in the Park:
“I like to play chess with old men in the park. Of course the tough part about playing chess with old men in the park is finding 32 of them.”    (2010 Edinburgh Fringe Festival - voted worst joke)
 
Facebook
Emo Philips
November 5, 2013 ·
I like to play chess with old men in the park. (The tough part: finding 32 of them.)
 
Reddit—Jokes
‘I like to play chess with old men in the park….
submitted May 23, 2017 by ZimbaZumba
... although it’s hard to find 32 of them.’