“How the hell did Marion Barry get his job back? Smoked crack and got his job back. How the hell did that happen? I mean, if you get caught smoking crack at McDonald’s, you can’t get your job back. … Marion Barry! Come on, how you gonna tell little kids not to get high when the mayor’s on crack?”

—Chris Rock

Say what you will about Marion Barry—and let’s face it, there are many, many things that one could say about the Chocolate City’s most famous politico—one thing is clear: When it comes to achieving iconic status among American mayors, Barry is right up there, at the very top.

This is no small achievement, given that the three-time mayor/current D.C. Council member has had so much competition: Just this year alone, we’ve had Portland’s first openly gay mayor caught up in a sex scandal involving a minor, and the Jersey mayors doing dirt with the rabbis. If you go back a century or so, there’s New York’s infamous Tammany Hall, by which many a mayor strong-armed his way to real power, and Boston’s Victorian era mayor, James Michael Curley. There’s Chicago’s original Daley Machine; Atlanta’s convicted mayor, Bill Campbell, doing time for tax evasion, and, let us not forget, Detroit’s Kwame Kilpatrick, who demonstrated what sexting is all about.

But Marion Barry, as made clear in a new HBO documentary airing today, The Nine Lives of Marion Barry, knows how to get involved in a scandal, do a little time for said scandal, rebound with a major reelection bid, get arrested for drunken driving, get married four times while engaging in philandering of epic proportions, do a little time in rehab, survive cancer, get arrested on charges of tax evasion, get reelected for city council, and then, this summer, get arrested for, of all things, stalking an ex-girlfriend.

So Barry is indeed iconic, iconic in that a so-outrageous-that-Chris Rock-felt-compelled-to-craft-a-standup-monologue-about-him kind of way. Among city politicians, it’s hard to find a more polarizing figure: Many loathe him, yes, but there are those who love him with a fierceness. As the promo line for the documentary reads, “To Know Him Is to Love, Hate, Praise, Scorn, Admire, Vilify Him.”

Traditionally, there have always been three Washingtons:  The mainly white  Northwest D.C. that controlled the purse strings and the power; the bourgie Gold Coast D.C. of the so-called mulatto elite; and the disenfranchised regular black folks who made up the bulk of the city. In the past decade or so, D.C. has morphed into other incarnations as well: Ethiopian D.C., Salvadoran D.C., South Asian D.C., West African D.C. and, most recently, boutique city D.C., with the $3,000-a-month rents, Barneys Co-op and sustainable seafood restaurants. Those are not Barry’s people. Barry’s people are to be found a scant two miles from the White House; they know him as a man of the people, a mayor who helped bolster the ranks of D.C.’s black middle class, a man who likes to take the credit for creating “a lot of black millionaires.”

“For those people who are Barry haters, this movie puts it into perspective,” Barry says in the documentary, which is directed by Dana Flor and Toby Oppenheimer. “Washington isn’t nearly the same it was. … I made a lot of black people fairly rich, including Bob Johnson.”

To understand the Barry love, it helps to remember that Barry came to power at a time when cities were in decline, but when black city politicians were in the ascendancy: Atlanta’s Maynard Jackson, Detroit’s Coleman Young, Cleveland’s Carl Stokes, Gary’s Richard Hatcher. Parliament Funkadelic’s “Chocolate City” encapsulated that sense of hope and dominion:

There's a lot of chocolate cities, around

We've got Newark, we've got Gary

Somebody told me we got L.A.

And we're working on Atlanta

But you're the capital, CC

The last percentage count was eighty

You don't need the bullet when you got the ballot

Watching Nine Lives, we see how Barry’s decline and drug addiction paralleled the Chocolate City’s descent into ’80s- and  ’90s-era crack madness. We see him just starting out, a Mississippi native and onetime Ph.D. candidate, learning his political chops under the tutelage of Martin Luther King Jr. and the Student Nonviolent Coordinating Committee, and from there, his progression to a dashiki-clad rabble-rouser (Jesse Jackson’s description) and “militant Negro” who was constantly getting arrested for challenging the status quo, to the savvy, suit-wearing politician who would sweep into city office on a promise of change.

You watch the documentary, taking a trip back in time, witnessing Barry’s many travails and Phoenix-like transformations, but come no closer to understanding the man: What’s driving his seeming incessant need for the spotlight? Ego? Insecurity? Both? Why did he leave academia for the political life? Why, as the inestimable George Clinton once lamented, in “Atomic Dog,” must Barry always chase the cat—well into his 70s?

Ultimately, though, one thing is clear: He’s the consummate ham, mugging for the camera in his clay face masque (“I’ve got the smoothest skin in D.C.”), preening in the mirror, fixing his hair just so, trolling the streets of D.C., meeting and greeting voters, and, in June, at Silverdocs, the world premiere of Nine Lives, taking an extravagant bow for the crowd.

No one, it seems, loves Marion Barry like Marion Barry loves Marion Barry.

Teresa Wiltz is The Root’s senior culture writer.