Come Back to the 9-5, Dave Chappelle, Dave Chappelle

I recently killed my MacBook when my car’s wildly substandard cupholder failed – where’s the goddamn recall on this, Toyota? – and dumped a grande chai latte into my laptop bag. It was a million-to-one shot. That latte had to fall in a ridiculously precise degree of arc to pour the way it did – directly into the machine. I decided to take it as a Sign.

I’d had that MacBook for about two years, after having been talked into it by longtime Apple disciple friends. I’d been a strict Windows man previously, and despite all the flowers and promises of the Apple crowd, I never did like that stupid Mac.

Resolved to stop drinking Apple’s OS Kool-Aid, I went out and got a big honking HP Windows “Entertainment Notebook,” which weighs about 40 pounds and has a screen larger than most art house cinemas. It’s glorious, does everything but make espresso, and often causes citywide brownouts when I plug it in at the local coffee shop. I love it. It’s the 1979 Lincoln Continental of laptop computers – black, shiny and mean.

I spent a few hours salvaging what files I could of the old MacBook, and nestled somewhere in the arcane and unknowable structure of Apple OS’ file management system, I found an old audio copy of the Dave Chappelle HBO special Killin’ Them Softly.

I hadn’t thought much about Chappelle since his conspicuous departure from Comedy Central a few years back. Like everyone else who was paying attention, I was a huge fan of Chappelle’s Show. Yet once Chappelle went off the radar, life – as is its wont – went on.

So I was excited to listen to the HBO show again, to see if it was as good as I remembered. Dropping the needle on the record, digitally speaking, I hit ‘play’ and started field-stripping the Mac.

Pretty soon I was too paralyzed with utter admiration to do anything but sit back and marvel. For my money, Killin’ Them Softly” is one of the all-time great stand-up comedy performances ever recorded. This is Chappelle in his prime, and if you haven’t experienced this particular show, I kind of envy you. You get to hear it for the first time, something I can never do again — short of trauma-induced amnesia or chemical lobotomy, neither of which I am ruling out as an option down the line. I’ve been looking for a way to forget the GWB years, anyway.

I’m a bit of a comedy nerd, and find the volatile alchemy of stand-up comedy to be forever fascinating. (For a great primer on this stuff, check out the “On Comedy” series from, which features in-depth interviews with stand-up comics discussing their processes.)

For the next few days, I sorted through the other comedy records I had on the old machine and moved them all over to the iPod. I like to listen to comedy albums when traveling — laughing continuously on the train tends to keep other commuters at a comfortable distance.

So I steeped myself in stand-up for about a week. I’ve got a lot of good stuff that I’ve appropriated from various sources over the years. The Best of Bill Cosby. All the Bill Hicks and Mitch Hedberg records. Patton Oswald. David Cross. Old Eddie Murphy and Richard Pryor routines. Ricky Gervais. Eddy Izzard. Louis CK. A bunch of Seinfeld. This new kid Daniel Tosh, who epitomizes the enduring but dubious comedy choice of verbal aggression over cool confidence.

They’re all good, no doubt, but put end-to-end with Chappelle in his prime, and it becomes evident that Dave really was something special. For starters, he is the king of cool confidence. Like Cosby, Chappelle can simply tell stories — for hours, if need be. Literally. For a couple years now, Chappelle and Dane Cook have engaged in a running stand-up endurance contest at L.A.’s Laugh Factory.

He’s also a polished performer, of course, and positively dangerous in his mastery of stand-up tradecraft. Aside from the jokes themselves, you can enjoy a Chappelle performance from a totally analytic point of view, just admiring the clockwork precision of it all. He’s a natural.

At the risk of trying to dissect humor – a perennially doomed proposition – I want to just isolate one element of Chappelle’s act. I’d contend that a big part of Chappelle’s appeal is in the artfully inconspicuous but genuinely heartfelt moral charge of his comedy. Obviously, I don’t mean morals in the old temperance and go-to-Church-on-Sundays sense. Chappelle’s is a much more modern morality, and he smokes too much weed to qualify for sainthood, anyway. Read between the jokes, and you’ll see throughout his work a simple sentiment: Racism upsets and baffles Chappelle.

The good news for us, his audience, is that Chappelle never lets his outrage curdle into anger or overt meanness. Instead, he uses all the tricks of his trade to turn that outrage inside out, toward laughter and a kind of shared incredulity.

From what I’ve been able to gather online, Chappelle left Hollywood for the noblest of reasons – because it’s a soul-sucking wasteland of greed, racism and submission to the lowest common denominator of broad demographic appeal. Or can be, at any rate. While he still performs regularly, Chappelle now lives a low profile life far away from the entertainment industry fastnesses in LA and New York.

Chappelle hasn’t produced anything in film or TV since 2006’s Dave Chappelle’s Block Party. He lives quietly with his family in Ohio. After leaving Chappelle’s Show in 2005, he retreated to South Africa for a kind of spiritual retreat. He would later disclose – on Inside the Actor’s Studio, of all places, that he left because the spirit of the show was changing.

“ I would go to work on the show and I felt awful every day, that’s not the way it was… I felt like some kind of prostitute or something. If I feel so bad, why keep on showing up to this place? I’m going to Africa. The hardest thing to do is to be true to yourself, especially when everybody is watching.”

Of his time in Africa, he said:

“It quiets the ego down. I’m interested in the kind of person I’ve got to become. I want to be well rounded and the industry is a place of extremes. I want to be well balanced. I’ve got to check my intentions, man.”

I think we can all agree, this is not the usual celebrity chatter.

While I certainly admire Chappelle’s conviction, and the courage it takes to walk away from sure-shot fame and fortune, I feel a real sense of loss when I watch those old stand-up routines and Chappelle’s Show DVDs. If he’d stayed the course, and somehow managed to navigate the treacherous waters – well, just imagine. We’d be enjoying Chappelle’s Show Season Eight. The world would be a better place. Spring would come earlier, melodies would sound sweeter, little kids would smile bigger and the polar ice caps would stop melting, and just maybe, we might all understand and treat each other just a little bit better.

What, too much to read into the relative pop culture absence of a stand-up comedian? Hmm. No, I’m sticking with it. Zip it up and zip it out!

Come back, Dave. We need you.