My Night with Dave Chappelle on Tour

Waiting for Godot?
The crowd was eclectic – an odd mixture of hillbillies and hip-hop heads, a sea of whites peppered with smatterings of black folks. Middle-aged parents sat in taupe folding chairs side-by-side to their giddy teens. A silver-haired African-American couple, both 60 if a day, glided by. A 50ish Asian man bobbed his head off-beat to the treble-heavy rap screaming from stage speakers as he hugged his way down a tight row with his male partner.

“Will he show up?” I sneered to my husband, the selfsame man who’d hit the web one recent Saturday morning and ponied up $150 to score two of the hottest tickets in town. As the Lake Erie-cooled August breeze filtered beneath the outdoor alabaster canopy that is Cleveland’s Tower City Amphitheatre, the two thousand-plus throng of concert-goers buzzed with eager impatience.

Suffering through the overdrive antics of a cussin’ hype man and blaring “bitch-and-ho” music designed to pump people up, the sellout swarm waited. It wasn’t that the expletive-laced lyrics were foreign to the shtick produced by the main man of the night, but because they embodied so much whipped-cream fluff atop the deep-down espresso fullness that is Dave Chappelle – rich, sharp, and enticing enough to compel all types of people to sit for hours, hoping for a taste of his brilliance.

Master Bait
By 10:30 p.m. the lanky comedian had strolled with a humble gait to the microphone; the congregation rose to their feet and formed a forest of warm-rounded cheering, tilting gazes and straining to glimpse the elusive figure live-and-in-person. He didn’t disappoint.

Flanked on either side by two big-screen images hoisted in the night sky magnifying his mouth to gargantuan proportions as he sucked cigarette after cigarette, Chappelle reeled in the multitude from the get-go with tales of his restaurant run-in with a popular starlet to his hilarious self-pleasuring routine.

“I saw Jessica Simpson at Barney’s in Hollywood,” Chappelle said, silencing the crowd, causing adult males and young boys to slouch forward with jealous angst. “She leaned in to kiss meâÂ?¦and I opened my mouth,” he said. “I just had to get a taste of that whiteness.”

Next Chappelle regaled his listeners by describing his hilariously-relatable masturbation ritual, mimicking himself stooping down stealthily in his shower, cocking an ear toward the door and listening for noises of familial interruptions. Funnier (and somewhat sadder) still were recounts of having his Yellow Springs, Ohio, house all to himself while timing his orgasms not to coincide with camera shots of “big man butt” in porn movies.

Life With Wifey
“It keeps me out of a scandal,” Chappelle said of his chain yanking, distancing his scandalous Comedy Central departure far away from anything as sinful as adultery. “I’ve never cheated on my wife,” he declared, swelling the crowd’s admiration, especially after listening to Chappelle’s yarn about being offered a dozen ready-and-willing naked women in a hot-air balloon at 9 o’clock in the morning.

Life with his wife, Elaine, and their two children is a subject Chappelle normally doesn’t broach. And though he alluded to marital drama during a former viewing of the genocide movie Hotel Rwanda, the megastar back-peddled from directly discussing any interracial incongruence within his union to a woman of Filipino descent.

“My wife…” Chappelle paused, waving off the topic with a bony hand, “that’s a whole ‘nother set of issues.” The collective heart of the crowd begged the maven of race relations to delve deeper by offering insight into his own personal United Nations, but Chappelle didn’t bite. Instead, he satisfied inquiring minds with details from his hot pursuit of Elaine, who made him wait to have sex during their courtship.

Now six years later, the bloom of conquest seems to have wilted from the matrimonial rose. “A show based on the first year of my marriage would’ve been called You Tricked Me,” Chappelle quipped, saying that these days he’d love for his wife to just close the bathroom door.

Religion and Politics
The then 32-year-old was equally tight-lipped about his belief in Islam, a religion that Chappelle converted to circa 1998. Shards of his faith trickled out during the show, however, when he referred to Jesus as merely “one of God’s prophets,” careful not to say Christ or Messiah. Aside from a true-as-beans monologue wherein America got the jump on the devil in sending the country straight to hell, Chappelle stayed away from the arena of religion.

But he boldly delved into the incisive sociopolitical commentary that has fueled his Phoenix-like rise above the ashes of baser-minded funny men. “I knew Saddam Hussein didn’t have any weapons of mass destruction, because we don’t invade countries that have them,” he said, recalling that North Korea’s literal demonstration of nuclear power provoked no response from the U.S.

As Chappelle seamlessly discussed everything from Afghanistan, Lebanon and the war in Iraq to Hillary versus Condi in potential presidential bids, he revealed a deep-thinking observer of global economy and human nature, a man willing to escape and hit the reset button in his own world instead of selling his soul – love of money be damned.

Chappelle’s “Lost” Episode
“I was only gone two weeks!” Chappelle proclaimed about his infamous retreat to South Africa to get his head together. He put his disappearance into perspective by juxtaposing the media-hyped hunt for both him and Natalee Holloway, the teen who disappeared in Aruba, against the minimal-to-nil search attempts undertaken when everyday African-Americans go missing. He summed it all up with, “I’m just saying that when I went away it was the first time they ever sent out a search party for a black person!”

In February 2006, much of the world watched Chappelle’s halting yet penetrating attempt to explain his departure during his first televised interview since his return to the states on The Oprah Winfrey Show. But later Chappelle admitted that he deliberately side-stepped some of the iconic interviewer’s questions.

More glimpses at the conflicted comic genius followed. Kevin Powell’s exquisitely in-depth cover profile “Heaven, Hell, Dave Chappelle,” for the May 2006 Esquire got as close as any reporter had thus far to the man that everybody wanted a piece of.

Pimps Up, Hos Down
That chase has only grown stronger. HBO is courting him, Chappelle said, employing his wooden stool for a quick object lesson on why he’s tarrying on a return to TV. “Imagine this stool is a pile of $50 million,” Chappelle explained, invoking obligatory moans from onlookers. One woman reached for the invisible lucre and drew it toward her body.

“But wait,” he warned, flopping his phallic microphone atop the stool. “When you try to take it, someone puts their [penis] on top of it.” Minds furrowed at the analogy of getting rich at the expense of dealing with hefty slave-like strings attached. Chappelle moved on to Iceberg Slim’s cautionary book, Pimp: The Story of My Life, to further explain.

“It’s not funny,” Chappelle warned before describing a scene from the memoir, “but it’s interesting.” He went on to tell the story of a washed-up hooker who felt indebted to her pimp after he tricked her into thinking he helped her beat a murder rap. Chappelle didn’t want to be that forlorn prostitute, nor be controlled and used like a pimped puppet.

Finally, the beleaguered satirist turned to a modern-day cult classic to clarify his illusiveness. “What’s the first rule of the Fight Club?” he asked. “You don’t talk about the Fight Club,” the flock replied. “Right,” Chappelle said. “I’m not trying to get killed.”

All in all, what is clear is that this humorist has seen the upper echelons of a world many never see – one swirling with blinding greed and unequaled manipulation – and decided to drop back down to earth to find some real love, love he asked his audience to always have for him seconds before departing the stage. “Yes!” we shouted in unison as we gave him his second roaring ovation of the evening. Love indeed abounds.

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