“I was thinking about starting an awning company, but that’s a pretty shady business to get into”

There are several jokes that making awnings is a “shady” business. “Because a man makes awnings it doesn’t always follow that he is engaged in a shady business” was printed in the Carlisle (PA) Herald on July 17, 1890. “RATHER shady business—Making awnings” was printed in the Bolivar (TN) Bulletin on August 1, 1890.
 
“All awning installers run a shady business.  (Syman Hirsch)” was posted on the newsgroup alt.humor.puns on October 5, 2001. “I was thinking about starting an awning company, but that’s a pretty shady business to get into” was posted on Reddit—Dad Jokes on June 21, 2018.
   
               
17 July 1890, Carlisle (PA) Herald, pg. 3, col. 1:
Because a man makes awnings it doesn’t always follow that he is engaged in a shady business.
 
Chronicling America
1 August 1890, Bolivar (TN) Bulletin, pg. 4, col. 5:
RATHER shady business—Making awnings.
 
16 August 1890, The Carroll Banner (East Carroll Parish, LA), pg. 4, col. 5:
RATHER shady business—Making awnings.
   
Google Books
14 July 1906, The Rural New-Yorker, pg. 564, col. 1:
HUMOROUS
“That man has a very shady business record.” “Why, what has he been doing?” “He puts up awnings.”—Baltimore American.
 
Google Groups: alt.humor.puns
Puns of the Weak 10/5/01
Stan Kegel
10/5/01
(...)
All awning installers run a shady business.  (Syman Hirsch)
 
Twitter   
Brodie Santeze
@ImminenTBrodiE
Sign on an awning truck!
OURS IS A SHADY BUSINESS!
1:37 PM - 9 Oct 2011
   
Twitter
Eric W. Poe
@epoepoe
The awning company runs a real shady business
7:07 PM - 17 Jul 2013
   
Twitter
Cole and Eric’s Puns
@PunsFoCash
Don’t trust awning salesmen. It’s a shady business.
-Eric
4:22 PM - 19 Aug 2013
 
Reddit—Punny
I just got a job at a place that makes awnings (self.Punny)
submitted October 13, 2014 by jskoker
Its pretty shady business…
 
Twitter
Lindsay
@Rollinintheseat
I want to open an awning company and call it A Shady Business.
2:41 PM - 20 Jan 2015
 
Reddit—Dad Jokes
When someone says their friend runs a shady business… (self.dadjokes)
submitted November 20, 2015 by Dartmuthia
“Oh, you mean like awnings or something?”
 
Reddit—Dad Jokes
I was thinking about starting an awning company. (self.dadjokes)
submitted June 21, 2018 by whatisthedealnow
But that’s a pretty shady business to get into.