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. (SeeKeeping it Real)
Chappelle showskit 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"
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.