Dave Chapelle The 50 Million Dollar Man!

Oh Snap! It's the 50 Million Dollar Man!

In a writing career that any scribbler should envy (even with the Zelda) F. Scott Fitzgerald seriously stumbled only once, when he wrote "There are no second acts in American lives."

Which brings us to Dave Chappelle.

Saw him last night at Toronto's Massey Hall. Read the reviews, and as far as they go, they're fine. You get the idea here. The short list? Is he still funny? Yes. Does he talk about why he walked away from his show? Yes. Is he crazy? Nope. And that's what scares me.

For a storyteller of any stripe, seeing Chappelle stalk the stage was an exhilarating and simultaneously unsettling experience. Exhilarating because his control and pitch are so exact. He's got a sense of timing and pacing that's unparalleled. He fills the stage -- one guy with a mike, smoking a cigarette every few minutes. His segues are seamless, his material never less than sharp. He can go from a serious political run to scatological lowest-common denominator material and back, and never seem like he's pandering. It's all fiercely smart. But more than that, it's confident, in a way I've rarely seen. I remember seeing Robin Williams years ago, post-Mork, pre-Good Morning Vietnam -- and though he was hilarious, it was such a self-conscious, throw everything at the wall and see what sticks train smash, that there was something about it that seemed unseemly.

Chappelle, on the other hand, stands up there and really seems like he doesn't give a fuck. Now, I know some of that is comic pose. But not all of it -- and that's what brings me to the unsettling part.

Because Dave Chappelle is undoubtedly a changed man. If you go back and see his standup specials from around the time Chappelle's Show debuted, or just before, and compare that to the guy on stage now -- it's clearly not the same guy. He's seen some dark shit, and it's changed him. There's something sad in his delivery that wasn't there before. You don't need to go too far to see an angry black comic. But Dave Chappelle will chill you, son. Because he's not just raging against the machine. You don't doubt for a second that he's seen it up close, felt the breath on his neck. For anybody who makes their living off creative labors... it's just... uncomfortable.

All black comics variously trade in some version of jokes about The Man...but when Chappelle stands up there and looks out at a largely white audience and says, "I don't mean you...you're not the real white people. I've met the real white people..." it's not paranoia talking -- it sounds -- it feels utterly reasonable. One of the lines I loved last night was when he talked about some of the truly rich people he's met, and asking one how he got so rich. After the traditional old-money disdain for the question, comes the punchline: "if you must know...my family holds the patent on fire."

When he compares the United States to M.C. Hammer, and asks, "what if the truth is that the United States is living a lifestyle it cannot afford?" He may be asking something that any number of left wing critics or academics have been asking for years. But the difference is: he had a seat at the table and walked away.

See, to see Dave Chappelle is to drink in the dissonance of the stories that we've all been reading about him for the last year. Because he does point out to you that there were six media companies that all spread the story about how crazy he was for walking away. You've heard so much about how crazy he is, that to see the fiercely smart, lucid, insightful guy stalking the stage is to make you wonder, just for a second, if the fix really is in, and why?

The thought of walking away from fifty million holds the same sick fascination for me as it does, probably, for most of you. How does a guy do that? What Chappelle does on this current tour is stand up there and tell you why. And damnit if you don't start to believe him.

You can climb the ladder of success in a creative operation, a creative career. You can make good money. You can buy houses, or afford a car, but you always have to keep in mind that you're not the person with the real money. And that every choice you make, every compromise, pulls you a little tighter.

So how do you walk away? Chappelle started with a metaphor, pointing at the stool on the stage, and saying, "that's fifty million dollars." And then the moment you reach for it...thunk...he drops the mike down on the stool. There it is, a big dick on top of the pile. He shakes his head. "I just couldn't figure out how to get that dick off the money."

My favorite part of the show wasn't the funniest, by any means. In a ten minute monologue at show's end, Chappelle tells a story of legendary Pimp Iceberg Slim. It's a story of how he got one of his 'ho's to keep working long after she should.

Chappelle has the story honed to a laser -- it's his best illustration, his main metaphor, for letting you in on The Game -- and by the time he comes to the punchline, well, if you're smart, you can see why he walked away. And you respect him for it.

Because if you're like me, deep down, you fear that you couldn't have had the strength to make the same choice. And much as I'd love to have a successful creative career - I hope I never have to find out.

Hobson was a fictional character. But a Chappelle's Choice? Well...that one's the thing, isn't it?