“My favorite position is CEO” (“A woman’s favorite position is CEO”)

“My favorite position is CEO” (or “A woman favorite position is CEO”) is a jocular line that has been printed on many gift items, such as bumper stickers, T-shirts and coffee mugs. “A woman’s favorite position is CEO” has been cited in print since at least January 1999, when it was spotted on a bumper sticker.
 
“My favorite position is CEO” was cited on Twitter on March 25, 2009.
 
   
Google Groups: alt.christnet.theology
New sayings that should be on buttons…
robert pavlik
1/11/99
(...)
67. A woman’s favorite position is CEO.
       
Google Groups: pdx.singles
HUMOR: You! Off my planet!
Scott Rainey
1/21/99
[This list is longer than I usually share, but most of these are new to me and all are amusing—slr]
               
Sayings that should be on bumper stickers, T-Shirts, or buttons:
(...)
A woman’s favorite position is CEO.
 
23 January 1999, Arizona Republic (Phoenix, AZ), “Retrying Keating ‘a shame,’ friend complains” by Eileen Bailey, pg. 1:
BUMPER SNICKER: Seen on a black BMW: “A woman’s favorite position is CEO.”
   
Google Groups: alt.humor.puns
Puns of the Weak 09-19-03 Part II The Rest of the Puns
Stan Kegel
9/19/03
(...)
A woman’s favorite position is CEO. (E4Fun)
 
Twitter
licketySplitAUS
‏@licketySplitAUS
A woman’s favorite position is CEO.
3:06 AM - 5 Nov 2008
 
Twitter
Kimberly Steward
‏@KimberlySteward
@TJsDJs My favorite position is CEO.  Lol
10:03 PM - 25 Mar 2009
   
Us magazine
Lauren Conrad Answers What Her Favorite “Position” Is: Video
February 9, 2014 @ 10:05 AM
By Stephanie Webber
(...)
During an appearance on Sway Calloway’s Sway in the Morning, Conrad, 28, pulled several questions out of a hat to answer. She quickly replied to all of them, but got stuck when asked: “What’s your favorite position?”
 
Silence.
 
After an awkward pause, she quipped: “CEO.”
   
Google Books
The CEO’s Little Surprise
By Kat Cantrell
Buffalo, NY: Harlequin
2016
Pg. ?:
Cassandra Claremont’s favorite position is CEO—and she’s sure as hell not stepping down for Gage Branson, the sexy playboy who once broke her heart.
 
Twitter
Misha!
‏@MishaLaurennn
Dear man in public wearing the “My favorite position is CEO” shirt, I applaud you.
7:23 PM - 3 Jun 2016