Thanks to comedian mastermind Dave Chappelle, the phrase When keeping it real goes wrong will forever be immortalized in pop culture history (we dare you not to laugh). Chappelle's hysterical skits themed around good situations gone bad became a staple of the sketch comedy show, and despite its end after three seasons in 2006, the impact still lives on. So much so, a Google Image search yields hundreds of hilarious photos. What follows are the 20 funniest pics we found when searching When Keeping It Real Goes Wrong. All hail Chappelle.
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