Chance the Rapper's funny "Elderly Aldermen" shows why it's so tough to win an aldermanic seat

Chance the Rapper's new video on the Chicagoist explains why it's so tough for young people who are not incumbents, like Chicago teacher Erika Wozniak, running in the 46th ward, to win elections to Chicago's city council.

Erika Wozniak Francis, pictured with Chicago Teachers Union organizer Marty Ritter, is running for alderman of the 46th Ward. The Chicagoist video features many young candidates who are running in some of Chicago's 50 wards. (Facebook photo)See Chance's 15 minute video, which also stars Chicago public school alumnus and comedian Hannibal Buress, on YouTube at

A Chicago Tribune report on the video and Chance's acquisition of the Chicagoist follows:

Analysis: Chicagoist returns: Chance the Rapper stars in comedic deep-dive into Chicago's aldermanic politics

By Nina Metz, Chicago Tribune

When Chance the Rapper hosted “Saturday Night Live” a year ago last November, it was his sly comedic timing and ease in the sketch format that jumped off the screen. He’s putting that talent to use once again, this time in a video posted on YouTube Friday.

Spoofing corny local investigative TV news reports, a bewigged but obviously recognizable Chance stares directly to camera and intones: “Today we will look into something so grand, so mysterious, so important — today we will look into the aldermanic elections of Chicago. What does it take? How does it work? And most importantly, what is an alderman? Let’s ask the American people and find out.”

Over the next funny and genuinely informative 15 minutes, ace reporter Champ Bennett (a riff on Chance’s given name, Chancelor Bennett) delves into the hows and whys of Chicago’s city hall and the murkiness of ward politics in general.

The video — which has a few things in common with John Oliver’s deep-dives on HBO’s “Last Week Tonight,” along with a pinch of “Schoolhouse Rock!”-esque animation thrown in— is the inaugural effort from Chicagoist, the local digital news site that ceased operations last November and was later sold to Chance over the summer.

The video is is the inaugural effort from Chicagoist, the local digital site that ceased operations last November and was later sold to Chance the Rapper over the summer. This is the kind of digital content Second City should have have been doing for years now; it certainly has enough people with the right kind of talent, but as a producing entity Second City hasn’t shown much interest in this kind of in-depth nuts-and-bolts style of infotainment. Maybe it’s too local for what Second City’s after, which is probably for the best — Chance has a larger reach, a more civic-minded purpose and, specifically, an interest in centering the views and opinions of young people of color.

Here’s some interesting context: The video (titled “Elderly Aldermen”) comes on the heels of the Chicago-set heist film “Widows,” which includes a major plot thread following a campaign for alderman between an entrenched white political dynasty and a black challenger. The forthcoming CBS drama “The Red Line” (currently filming in town) also includes an aldermanic candidacy that pits a young upstart against a longtime incumbent. Both “Widows” and “The Red Line” make explicit the ways race and racism — and money and connections — figure into Chicago politics.

Champ Bennett reports on what an alderman actually does, what it takes to become one and the obstacles that prevent young people from running for office. Chicago Aldermanic elections: February 26, 2019 The video from Chance and his Chicagoist collaborators is written by him, Chicago-based activist and journalist Charles Preston, Colleen Mares (one of Chance’s managers) and Sam Bailey, the co-creator of the web series “Brown Girls.” Bailey is also the video’s director.

Notably, the video was posted just one day after federal agents raided the office of Ald. Ed Burke, who has held office since 1969. As my colleagues deftly put it in their reporting, Burke is the kind of city politico who has “been at the center of Chicago’s longest-standing political power structure” for decades. Bearing that mind, the Chicagoist video functions as something of a primer on what’s a stake, broadly speaking, when incumbents get too comfortable and remain in office indefinitely — and why Chicagoans should investigate more deeply who they vote for and why.

Hannibal Buress (a Steinmetz High School alumnus) guest stars in Chance the Rapper's "Elderly Alderman."The video also features Chicago native Hannibal Buress as fictitious Ald. Durhman, of the equally fictitious 51st Ward. (One of the helpful tidbits explained herein for those who don’t already know: Chicago has a total of 50 aldermanic wards).

So, how does an alderman serve the people of each ward, Champ asks?

“I take care of dem potholes on the West Side, permits, block parties, awnings,” Durhman says. “If you wanna start a bar, you want a liquor license, you gotta pay me off. People call my office about those boots on their car — it’s not my fault you didn’t pay your parking tickets, now your Altima has a canary-yellow Timberland. Pay your damn parking tickets, that’s a different department than me.”

A pair of puppet newscasters break in to underscore that yes, this description is actually pretty accurate. Aldermen wield considerable power over decisions large and small, and they have a $1.3 million budget to spend at their discretion.

Champ quizzes people on the street and also interviews journalists including Rashanah Baldwin, who explains that wards can be redistricted (essentially gerrymandered) in power plays by the mayor. Other issues are broached: Is it time for younger people to take office? (Burke is 74.) What about all those city hall caucuses — do they have any effect? What do alderman get paid anyway ($116,000) and how does money play into how decisions get made? Champ digs in.

The video is genuinely informative and legitimately entertaining, with a bit where Champ clumsily cleans his eyeglasses that alone is reason enough to watch it. I’ll repeat what I said when I reviewed his “SNL” appearance last year: If Chance hadn’t gone into music, he might have been a natural fit in the city’s sketch and improv scene. He’s a legit comedic performer, and he doesn’t overplay it here. Meaning, he doesn’t distract from the point of the video itself, which is a serious-minded examination of the role of alderman in this city.

The video’s creators have also made smart and specific choices about who’s voices they want to amplify: primarily black and Latinx Millennials, including aldermanic candidates such as Rossana Rodriguez (running for the 33rd Ward), Ugo Okere (running for the 40th Ward) and Cleopatra Watson (running for the 9th Ward). That framing is so often missing — and it marks Chicagoist’s re-emergence as a potential force to be reckoned with.

Upon hearing the myriad ways someone can be knocked off the ballot — sometimes based on technicalities that many younger candidates might be unaware of without the right insider knowledge — Champ observes: “That sounds racist.”

It’s notable that at a time when most news outlets continue to shy away from using that word, the newly reconstituted Chicagoist is signalling that it doesn’t share the same fear or reluctance, underscored by Public Enemy’s “Fight the Power” playing over the closing credits.

Going forward it’s unclear if Chicagoist will continue to use humor as a delivery device to arm viewers with vital but otherwise dry-seeming news and information. But it’s a hell of a start.


Add your own comment (all fields are necessary)

Substance readers:

You must give your first name and last name under "Name" when you post a comment at We are not operating a blog and do not allow anonymous or pseudonymous comments. Our readers deserve to know who is commenting, just as they deserve to know the source of our news reports and analysis.

Please respect this, and also provide us with an accurate e-mail address.

Thank you,

The Editors of Substance

Your Name

Your Email

What's your comment about?

Your Comment

Please answer this to prove you're not a robot:

2 + 3 =