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When Keeping it Real Goes Wrong 

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."

when keeping it real goes wrong 

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"

When Keeping it Real Goes Wrong 

The greatest Chappelle's Show skit ever, self explanatory.
You think it's a game nigga? BAH BOW

When keeping it real goes wrong 

Rockets vs. Lakers game 1.
"The Rockets-Lakers game 1 was a bad episode of When Keeping it Real Goes Wrong!" - Stat Boy.

Stinky Bobby

When you find a little guy who is stinky. Usually needs a belly rub.
Hey, that’s Stinky Bobby.
Stinky Bobby by anorlondo June 17, 2026
Word of the Day on July 29, 2026
A trip to a grocery store, convenience store, or gas station for the sole purpose of buying an excessive amount of junk food and sugary drinks, usually with friends. A chud run often happens late at night and ends with everyone involved hating themselves afterwards.
"Hey bro you tryna go on a chud run with me??"
chud run by chad brandson July 24, 2026
Word of the Day on July 28, 2026