“How much dip would a dipshit shit if a dipshit could shit dip?” (or “How much shit could a dipshit dip if a dipshit could dip shit?”) is a jocular line that has been printed on many images.  The “dipshit” version is a variation on the famous woodchuck tongue-twister—“How much wood would a woodchuck chuck if a woodchuck could chuck wood?”
   
“How much shit could a dipshit dip if a dipshit could dip shit?” was posted on the newsgroup alt.tasteless.jokes on June 2, 1997.
   
“How much dip could a dipshit shit if a dipshit could shit dip?” was posted on Twitter on March 22, 2011.
 
“How much flu would a flu shot stop if a flu shot could stop flu?” is a similar saying.
   
     
Wikipedia: How much wood would a woodchuck chuck
How much wood could a woodchuck chuck is an American English-language tongue-twister. The woodchuck from the Algonquian word “wejack” is a kind of marmot regionally called a groundhog. The complete beginning of the tongue-twister usually goes: “How much wood would a woodchuck chuck if a woodchuck could chuck wood?” The tongue-twister relies primarily on alliteration to achieve its effects, with five “w” sounds interspersed among five “ch” sounds.
 
Google Groups: alt.tasteless.jokes
THE SHIT MEMO
dragnfly
6/2/97
(...)
How much shit could a dipshit dip if a dipshit could dip shit?
 
Google Groups: fido7.ru.english
translation’s needed (literary one)
Alex Kozloff
2/24/98
Hi there, All!
Two days ago my mother presented me one thing. Just usual tea-cup. Nothing important. Also I need to add that my mother doesn’t know English at all. So looked at the box where this cup had been packed. It shocked me. There was written very fascinating thing. “How much shit could a dipshit dip if a dipshit could dip shit?” That’s all. Please, translate this (puzzle?) sentence. At least give me the sense of it.
 
Twitter 
Lisa Hall‏
@lisahall823
How much shit could a dipshit dip if a dipshit could dip shit?
2:59 PM - 3 Jun 2009
 
Twitter
Alex C Shives III‏
@Al3XIII
How much shit would a dipshit dip if a dipshit could dip shit??
10:33 PM - 18 Feb 2010
 
Twitter
Shelby Bennion‏
@shelbybennion
How much shit would a dipshit dip if a dipshit could dip shit?
12:03 PM - 2 Apr 2010
 
Facebook
Tuna At TheBuzz‎ to The Buzz 104.3 - Radio Station Rock Music US Virgin Islands Puerto Rico
October 14, 2010 ·
ooh! how much shit could a dipshit dip if a dipshit could dip shit?
-deep thoughts by Tuna while keeping it fresh…
 
Twitter
a 🦇d‏
@asultanov
how much dip could a dipshit shit if a dipshit could shit dip?
2:57 AM - 22 Mar 2011
 
Twitter
Lesley Morton‏
@LesleyMorton
How much dip could a dipshit dip if a dipshit could dip shit?
11:49 AM - 3 Oct 2011
 
Twitter
Ryan Shilling‏
@Shill_outbro
How much dip could a dipshit dip if a dipshit could dip shit?
11:01 AM - 14 May 2012
 
Twitter
SpectacularJoSh‏
@TalkAboutOssum
How much dip could a dipshit shit, if a dipshit could shit dip?
8:56 AM - 24 May 2012
 
Facebook
Cloyd Rivers
October 29, 2013 ·
How much dip would a dipshit shit, if a dipshit could shit dip? Merica.
 
Google Books
Off The Top Of Fred’s Head
By Fred Lavner
Lulu Books (Lulu.com)
2015
Pg. 179:
How much dip would a dipshit shit if a dipshit could shit dip?
 
Me.Me
HOW MUCH SHIT COULD A DIP-SHIT DIP IF A DIPSHIT COULD DIP SHIT? MEME
MEMES 🤖 DIP DIPSHIT DIPPING DIPS
FOUND ON 2017-02-09 08:26:10 BY ME.ME
SOURCE: FACEBOOK
 
Me.Me
HOW MUCH DIP WOULD A DIPSHIT SHIT IF A DIPSHIT COULD SHIT DIP CARDS EE USER CARD MEME
MEMES SHIT 🤖 HOW DIP USER DIPSHIT DIPPING DIPS CARDS CARD MUCH SHITTING HOW MUCH USERS
FOUND @ 2 LIKES ON 2017-04-04 14:01:54 BY ME.ME
SOURCE: FACEBOOK