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The year was 2003. It is was a simpler time really, when YouTube hadn’t yet provided us with one hit wonder after one hit wonder of sketch comedy and internet videos. Twitter wasn’t yet a thing, and access to celebrity didn’t exist. Basically, America wasn’t yet desensitized and overly entertained. We had television though, and a new weekly program that was set to transcend both race and comedy genius.
When Chappelle’s Show first debuted on Comedy Central, no one thought it would be anything special. It struck a chord though, especially among high school and college age folk. Through a huge word of mouth network – and one line quotes of the material – you could argue it started the trend of viral videos (that and Comedy Central giving every “it” comedian their own sketch show). Whether it was the Rick James vignette, or the Wayne Brady cop-killer bit, everyone had seen, heard or at the minimum was aware of the program.
Cut to a few summers later, with a new $55 M contract and insane amounts of pressure mounting, Chappelle up and left for Africa prior to the beginning of season 3 … Without warning he walked away from it all. Neal Brennan – co-creator of the show and good friend – said they would never work together again.
Leaving on top has only served to make Chappelle’s legacy that much stronger. We didn’t see him fall from grace, nor did we feel we got all that he had to offer. As a result, since then when Dave has been known to pop up from time to time at venues throughout the country, these impromptu appearances spark great nostalgia and lore among the comedy community.
Sunday for example, was just another normal night at the Westside Comedy Theater - tucked in an alley behind the hustle and bustle of the 3rd Street Promenade – in Santa Monica. Neal Brennan was set to do his weekly stand up show – Neal Brennan and Friends – with seasoned comedians like Greg Fitzsimmons performing alongside him.
And then enter Dave Chappelle … To close the show Neal brought his old buddy on stage unannounced around 10:30p. Dave rocked a backpack on his newly toned physique throughout the set, switching back and forth from pacing the stage to sitting on its lone stool. Relaxed, the performance was more conversational than normal, it was as if you were in on the secret with him.
To add to this special appearance, rather than stay in the green room, Neal sat in the audience and at times would chime in with a word or thought. The two would exchange some banter and then Dave would use that as fodder for his next riff. Most comedians work up their routines, start with 5 minutes, then 10, then 30, etc. All told, it was after midnight – closer to 12:30a actually – that Dave ended his set. A full two hours of pure bliss for those in attendance.
The price of admission for this intimate evening? All just $5 …
It was just one of those nights, a friend of a friend was there, and it was “legendary”. And as it turns out, the word of mouth that most people discovered Dave through still bolsters his legacy 10 years later.
Category - Pop Culture