“What’s 12 inches long and hangs in front of an asshole?”/“My boss’s tie.”

A political joke has been cited in print since at least 1990:
 
Q: What’s twelve inches long and hangs in front of an asshole?
A: Dukakis’s necktie.
 
Michael Dukakis was the Democratic Party’s 1988 candidate for U.S. president. The joke has also been told about conservative talk show host Rush Limbaugh, and politicians such as George W. Bush and Donald Trump.
 
A lawyer version has been cited in print since at least 1994:
 
Q: What’s eighteen inches long and hangs in front of an asshole?
A: The tie around a lawyer’s neck.
 
A work version has also been popular. “What’s fifteen inches long and hangs in front of an asshole? My bosses tie” was posted on Twitter by swollenvoice on July 15, 2013.
 
   
Google Books
Friday Night Lights:
A Town, a Team, and a Dream
By Buzz Bissinger
Reading, MA: Addison-Wesley Pub. Co.
1990      
Pg. 189:
What’s twelve inches long and hangs in front of an asshole?
Dukakis’s necktie.
   
Google Books
Flush Rush
By Brian Keliher
Berkeley, CA: Ten Speed Press
1994
Pg. 24:
Question: What’s 18 inches long and hangs in front of an asshole?
Answer: Rush Limbaugh’s tie.
       
Google Groups: rec.humor
Canonical List Of Lawyer Humor 1/3
Nuke The Unborn Gay Baby Whales For God
4/12/94
(...)
What’s eighteen inches long and hangs in front of an asshole?
The tie around a lawyer’s neck.
 
Google Books
Lawyers and Other Reptiles II:
The Appeal
By Jess M. Brallier
Chicago, IL: Contemporary Books
1996
Pg. 20:
Question: What’s 12 inches long and hangs in front of an asshole?
Answer: A lawyer’s tie.
   
Google Books
The New York City Bartender’s Joke Book
By Jimmy Pritchard
New York, NY: Warner Books, Inc.
2002
Pg. ?:
What is fourteen inches long and hangs in front of an asshole?
A lawyer’s tie.
 
Twitter
Porgy Tirebiter
@hiloecho
Q: What is fifteen inches long and hangs in front of an asshole?
A: Rush Limbaugh’s tie
11:16 AM - 15 Feb 2008
   
Twitter
nicholasclaxton
@nicholasclaxton
What is twelve inches long and hangs in front of an asshole? McCains Tie!
3:08 PM - 16 Sep 2008
   
Twitter
Frank Massaro
@Frank__Massaro
What’s eighteen inches long and hangs in front of an asshole?
George Bush’s tie.
10:28 PM - 5 Nov 2009
   
Twitter
Anthony Brady
@AJBrady_Sports
Replying to @YahooForde
@espn4d Say this to Ellen: “What’s 15 inches long and hangs in front of an asshole? A lawyer’s necktie.”
2:37 PM - 18 Nov 2009
   
Twitter
swollenvoice
@swollenvoice
What’s fifteen inches long and hangs in front of an asshole? My bosses tie.
8:01 AM - 15 Jul 2013
 
Reddit—Jokes
What’s 18 inches long and hangs in front of an asshole?
submitted September 22, 2015 by ClericPreston815x2
Donald Trump’s tie.
 
Reddit—Jokes
What’s 12 inches long and hangs in front of an asshole?
submitted April 11, 2016 by HungryAndFocused
Donald Trump’s tie.
     
Twitter 
Puneet Anju Gaur
@TheAlpha_Q
What is 15 inches long and hangs in front of an asshole?
My boss’s tie.🙄
12:02 AM - 22 Nov 2016
 
Reddit—Jokes
What’s 18 inches long and dangles in front of an asshole?
submitted February 10, 2017 by Itsprobablysarcasm
Donald Trump’s tie.
 
Twitter
donaldtrumpnewstoday
@irishrygirl
What’s 10 inches long and dangles in front of an asshole? Trumps neck tie!!!
8:42 PM - 2 Mar 2018
     
Reddit—Jokes
Whats 12 inches long and hangs in front of an asshole?
submitted August 25, 2018 by Duschbagg
My bosses tie
 
Twitter
Joe Passineau
@JoePassineau
You know what’s 12 inches long and hangs in front of an asshole?
My bosses tie
2:13 PM - 25 Aug 2018