In the act of Keeping it Real, the outcome is unexpected and usually has a negative affect on the individual who decided to keep it real. (See Keeping it Real)
After losing his Job, Frank wrote a paper on, "When keeping it real goes wrong."
by SouthParkChef July 22, 2008
The greatest Chappelle's Show skit ever, self explanatory.
You think it's a game nigga? BAH BOW
by General Crap March 07, 2004
Chappelle show skit that satirizes a situation where a person decides to act on impulse or acts uninhibited by social mores or norms (i.e. "keeping it real") which usually leads to adverse and often times unexpected results.
When keeping it real goes wrong in a board meeting at your corporate job when someone mimics, coopts, or imitates your culture in a condescending way and seeks your affirmation in doing so. (i.e. "Give me some skin, dawg"). Also referred to as "actin' your color"
by JNice007 March 02, 2009
Rockets vs. Lakers game 1.
"The Rockets-Lakers game 1 was a bad episode of When Keeping it Real Goes Wrong!" - Stat Boy.
by Richard Dean, Journalist April 19, 2004