Steve James and Rickey Hendon in November 2018 during a taping of yours truly's show Credit: Ben Joravsky

Early this morning—long before the sun—I was up in a panic. And I think I know why . . .

Got to stop watching City So Real right before I go to bed!

That would be the latest masterpiece from Kartemquin Films’s very own Steve James. One of the best documentary moviemakers—ever.

I’m sure you’ve read about it, if you haven’t already seen it. And if you haven’t—it’s on Hulu.

Not immediately obvious why it would set off such a panic in me. It’s far removed from the stuff that usually frightens me.

No ghosts or goblins. No psychos with long knives hopping out of closets. Or teenagers foolishly going down to the little home on the lake. It’s no Candyman, that’s for sure—speaking of great flicks set in Chicago.

No, it’s more like the film makes me realize—even if I’d rather not—that the city I’ve chosen to live in is a loony bin when it comes to politics. Especially race and politics.

Ostensibly, the five-part series is about the mayoral race of 2019. But it covers much more than that. Over the last three years, James and his film crew crisscrossed the city, dropping in on bars, restaurants, barber shops, community meetings, and protest rallies all over town.

It’s a portrait of Chicagoans, featuring a dizzying array of classic Chicago characters of all races and ethnicities. In fact, I’d say the actual candidates—including Mayor Lori Lightfoot—might be the least interesting characters in the movie.

You know the type of character I’m talking about. You may be one of them. Loud and brash. Braying one moment, bawling the next. A lot like each other, even if they ostensibly hate each other.

If only they could hear themselves or listen to the other guy, they’d realize how much they have in common. And then they wouldn’t be at each other’s throats.

Ah, probably not.

It’s the movie’s backdrop—our political system—that remains so frustrating. And I say this as a fellow who’s been obsessively following Chicago politics since about 1981.

That’s a long time ago—even before Steve James came to town. 

Back then, Jane Byrne was the mayor. I will withstand the temptation to recite more ancient political history. I’ll just say that Byrne emerged from old man Daley’s machine, and her victory led to Harold Washington’s election, just as his untimely death in 1987 led to what we have now . . .

What an old friend of mine called a kleptocracy, overseen by the corporate and civic elite, who don’t really seem to care too much about the plight of the peasants, so long as they make a buck.

The mayor’s race of 2019—with its large cast of characters—takes center stage in City So Real.Credit: Lydia Thompson / 21st Century Fox

Anyway, back to the mayor’s race of 2019. It was an exceedingly dispiriting affair, even by Chicago standards.

That’s because Mayor Rahm chickened out and dropped out of the race to avoid getting the ass-whooping he most definitely deserved. And would have gotten, I’m sure.

Alas, the peasantry lost the opportunity to unseat the king.

Obviously, James’s movie would have been much different had Mayor Rahm stayed in the race. But if you can’t be with the one you love, love the one you’re with. As the song says.

And so, James does the best he can to diligently follow the madness as over a dozen candidates go at it.

As the story of the campaign unfolds, it’s almost painful to watch how easy it is to crush the spirit of even the most idealistic of Chicagoans.

From my perspective, one of the movie’s great feats is to reveal how absurdly difficult it is to even make the ballot.

I could write a treatise on this subject—in fact, I have frequently done just that. Much credit to James for capturing it so concisely and vividly. Bottom line . . .

You need 12,500 voter signatures to make the ballot. Each of these signatures can be challenged by your opponent. An election judge renders a decision on that challenge. Either side can challenge the judge’s decision. Ultimately, handwriting analysts may be dragged in. Voters may be subpoenaed.

It drains a campaign of money, time, and energy. How is this healthy for democracy?

My old radio pal Rickey Hendon is the maestro of the challenge. In the end, Hendon manages to knock . . . oh, watch the movie yourself.

The people who run the election board wind up angry at Hendon, as though he’s the problem. Please. It’s the system that’s out of order—Rickey’s just playing the game.

So many compelling scenes in this movie, I can’t detail them all. Let me just close with this . . .

It’s a salon at Christie Hefner’s upscale apartment, featuring several movers and shakers, including Norman Bobins, a banker and former Mayor Daley school board appointee. (That’s baby Mayor Daley.)

As the dinner guests discuss the upcoming mayoral election, Bobins says he hopes we don’t go back to the days of Harold Washington.

Why is that? Someone asks. Too much chaos, he replies.

I wanted to wretch. There was no more chaos under Mayor Washington than under any mayor since.

Yes, I know all about the Council Wars. In which a band of white aldermen rose up to oppose the mayor.

But they made their deals to pass their budgets. And the trains ran. The garbage got collected. When you turned on the tap, water came out. Schools opened. And so forth.

The only difference is that Washington was a proud Black man who stood up for his community. And for that, the powers that be will forever try to scare white people into voting against any candidate who vaguely resembles him in style and ideology.

And so it goes in Chicago . . .

Much respect, Mr. James, for another masterpiece. It wasn’t pretty or sweet. But it was real, just like the title says.  v