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CIFF 2020: The Road Up & City So Real

October 29, 2020


Each year at the Chicago International Film Festival (CIFF) there are Chicago films to be discovered in the lineup, mixed in with all the ones that come from different countries. They could be narrative features set in the Windy City or documentaries that showcase the people who live there, often times providing a true representation of a people who are misrepresented, overlooked, or disregarded. It makes sense considered the name and location of the festival and as much as I do my best to seek out films from other lands, I realize that as a Chicagoan the stories that take place in my proximity should not be ignored. In fact, I feel compelled to seek out such films to be reminded or enlightened about the city I live in. “The Road Up” and “City So Real” are two such documentaries and watching them from my Chicago home during a pandemic found me missing the neighborhoods and downtown streets that I haven’t traversed since mid-March. Sure, we have many forms of technology to keep us connected, but watching these two films reminded me how much I miss being in the presence of friends – and surprisinglyI find myself missing the sounds and smells of the city I used to be so annoyed by (okay, I don’t miss rank smells of urine and weed on the CTA). Like one man says in “City So Real”, Chicago is a city I love and hate, and you can only say that when you live in it.

That being said, I’m grateful that I have a place my family and I can call home and that I can make ends meet, ultimately not wanting for much. I’m well aware not everyone can say that. Knowing that has often put me in the mindset of wanting to know how others live – what their struggles, dreams and accomplishments are. I was reminded of all this while watching “The Road Up” from co-directors Greg Jacobs and Jon Siskel and “City So Real”, the latest from master filmmaker Steve James.

Both films gave me so much to think about, providing introductions to people who are making an indelible (albeit unsung) impact in the lives around them and offering access to areas that are typically unexplored or unseen.

I’m thankful they were made and that they exist for all to see, especially for those who only know Chicago by how it is mentioned and reported on a national level, which is typically that is corrupt and one of the most violent cities in America. Well, there’s obviously so much more going on than just those two things and these two films give a detailed and focused look at current Chicago life.



THE ROAD UP (2020) 

After watching “The Road Up”, you will be changed and forever grateful to have been introduced to Jesse Teverbaugh, the charismatic leader of a month long “boot camp” called Transformations at job-training program called Cara in the South Loop of Chicago. He knows that those who take his course need to and could greatly benefit from a place that will help them get hired and stay hired for a year. He knows that it’s not easy to overcome challenges such as homelessness, addiction, and the weight of a criminal record, on your own. He also knows that his touch love delivery may be hard to take for some, which is why he follows it be building up his audience with hope and love. Co-directors Greg Jacobs and Jon Siskel introduce us to Teverbaugh and Cara, and four Chicagoans who must find their footing and navigate their way through this program. It’s not easy.

Many of them haven’t had someone in their corner believing in them, nor have they ever been given a chance to prove themselves and often if they have, they wind up blowing due to their own anxieties, bad decisions, or emotional issues. It’s a precarious and complex journey, one that requires open communication with Teverbaugh and Cara and the right decisions one day after the next.

Jacobs and Siskel (“Louder Than a Bomb” and “No Small Affair”) started filming in 2015, but the film sadly feels timeless, since there will always be those who need help, especially individuals who often get overlooked. I found myself eventually overcome with inspiration and emotion the more time spent with Tamala, Kristen, Clarence, and Alissa. As the quartet spend four weeks with Teverbaugh they are placed in jobs where they experience success, failure, and new opportunities. Through it all, “The Road Up” gives humanity and dignity to these flawed yet courageous people.

Teverbaugh is there to help those who come to his program know that they are not alone and that there is often much more to one’s struggle than finances. When Jacobs and Siskel eventually capture Teverbaugh revealing his backstory, it offers an understandable context to what we’ve seen him do. He’s a man who will easily be one of the most memorable human beings that I’ll encounter all year in my film viewing. “The Road Up” wound up blindsiding me with its real look at ups and downs of community, connection, and love in the face of adversity.

RATING: ****




CITY SO REAL (2020) 


Steve James’ “City So Real” is an ode to the city he calls home. For viewers who also live in Chicago, this 5-hour documentary will be a reassuring nod of the pride and frustration they have for their city. However, those who only know Chicago for Al Capone, Michael Jordan, and mounting violence, will be enlightened in many ways as the three-time Oscar-nominated filmmaker winds up humanizing the city with artful grace, potent honesty and keen observance.

This is an impressive film – er, mini-series – considering how personal it comes across, while covering a breadth of topics and neighborhoods. The length is understandable considering one of the subjects James is covering is the 2018/2019 mayoral election – which started out with 21 (!) candidates and wound up with Lori Lightfoot (the first black lesbian woman as an American major) winning – after Rahm Emmanuel opted to bow out/retire in the aftermath of the murder of Laquan McDonald, who was shot 16 times in 2014 by Chicago police officer Jason Van Dyke. James (“Hoop Dreams”), along with his longtime producing partner Zak Piper (“Life Itself” and “The Interrupters”), paint a detailed picture of the climate during that time with their incredible behind-the-scenes access to the respective campaigns and the voting process in the Windy City, with an emphasized focus on two fascinating young candidates, Amara Enyia and Neal Sales-Griffin, both of whom have seemingly incredible resilience and optimism considering the reputed corruption of Chicago politics.

While watching, I couldn’t help but wonder how James and his crew went about deciding who and what they would cover, not to mention how certain self proprietors were chosen – from a barber shop on the south side to the owners of the venerable music venue, The Hideout on the north side – and are revisited throughout the entirety of the project. The story told looks good too, with beautiful photography and precision editing by James and David E. Simpson that feels both intimate and broad in scope, in all the appropriate ways.

Although it is inevitably a Chicago-centric film, I’d wager one could relate “City So Real” to just about any major metropolitan American city. With a dash of Chance the Rapper and Yeezy, the Ed Burke extortion scandal, and an opening number by The Devil’s Woodpile, “City So Real” offers so much, one hour at a time.

The fifth and final is a powerful coda as any, catching us up with the city one year into Mayor Lightfoot’s election, just as COVID-19 and the protests following the killing of George Floyd. It’s poignant considering we’re still living in this climate. It’s as if we’re on the outside looking in at ourselves looking out, still uncertain for our future, yet hopeful.

RATING: ****


CIFF may be over with, having run it’s course from October 14th through October 25th, but you can catch these two documentaries in different ways very soon.

At this time, “The Road Up” is still seeking distribution and working the film festival circuit. Any news of that changing will likely be found right here.   Keep it on your radar, because it’s one of the best films of the year.

“City So Real” will be released on October 29th on the National Geographic Channel and on Hulu on October 30th.



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