Every week at SiftPop.com, we challenge our writers to choose what they think is the best movie under a certain topic related to a recent release. So this week, with the release of Candyman, we’re counting down our favorite movies set in Chicago! Let us know @SiftPop what your ranking is!
Remember when Tom Hanks signed on to play Mister Rogers and there was a general consensus that he probably was the most likable person of his generation? All of those people of course forgot about The Circle, as they well should, but they also forgot about Road to Perdition, because this marks the point where Tom Hanks finally played someone who was definitely not a good dude. Maybe you could call him the least bad dude, but he’s definitely not a good dude. As an enforcer for Paul Newman’s Chicago crime family, Hanks is present for the murder of a union boss — along with his son, hiding nearby. It’s the catalyst for a road trip to escape their old lives, hunted by Jude Law of all people. While the city of Chicago doesn’t play a tremendously big role in the film, it certainly provides enough of a mood for the foundation of the film before Hanks takes his son to Perdition, Michigan. (Chris Bakker)
In 1984, five teens at Shermer High School from various social circles discovered the shocking similarities they share. The Breakfast Club, directed by the king of teen high school films himself, John Hughes, truly encompasses what it means to be a teen. Despite being full of levity, the film does an excellent job of laying out how cruel social hierarchies can be and how they do nothing but divide our youth. Each of the performances come off incredibly authentic and I think that is one of the driving factors that has given the film the legs over the decades. Emilio Estevez, Judd Nelson, Molly Ringwald, and Ally Sheedy are exceptional, but a film is nothing without a proper antagonist. This is where Paul Gleason as Mr. Vernon enters the equation as the complete antithesis of what the kids in Saturday School stand for. He is completely out of touch with the adolescents he is responsible for and overlords them with a stern iron fist. Seeing the pack of teens slowly bond and rebel against the tyrannical Vernon is highly enthralling. It is humorous that the title song is called “Don’t You (Forget About Me)” because no one will ever forget this ‘80s Classics anytime soon. (Joe Vargas)
Biographical films can be a murky business. It can prove to be difficult to navigate the road between honoring the reality of someone’s life while also making a compelling film that gets people in the seats. I believe there are few biographical films that can rival Spike Lee’s 1992 classic Malcolm X. The movie lives and dies with Denzel Washington playing the titular character. Washington plays Malcolm with an incredible amount of poise and sincerity, showing an immense amount of respect and honor not only to Malcolm X, but also to his legacy. Lee does everything right. He takes the complex life of a man and shows us exactly the right moments to help us truly realize the magnitude of Malcolm X’s impact in society. While we shouldn’t rely on films like this to be our sole method of learning, it is through films like this where we can be introduced to an idea or an individual and then take it upon ourselves to do a deeper dive into the subject matter. Malcolm X is an indelible classic, a beautiful tribute, and a film I would recommend everybody sees at least once in their life. (Nashua Doll)
As my follow up to Do The Right Thing, this week I tackle the movie Judas and the Black Messiah, a film that I’m getting off the list of shame before it gets on it (there’s a two year grace period for new films if you’re curious). Starring Daniel Kaluuya and LaKeith Stanfield (one of whom should have been nominated for Best Actor. I mean, come on), this film dives into a story I regretfully knew little about prior to watching it: the infiltration of the Chicago Black Panther Party by William O’Neil and the assassination of Fred Hampton. Let me tell you this movie is heavy, with amazing performances wrapped around a story that is beautiful at times while haunting at others. At one moment, it will make you feel inspired and drawn to action, while at others (especially when Michael Sheen is on screen), it left me with the distinct feeling that I needed a shower. This film is truly a modern masterpiece and is high on my list of recommendations, if only for it to convince people to look into a portion of American history that should never be forgotten. (Joseph Davis)
This is the quintessential romantic comedy, and I won’t hear anything else. End of— oh, you want to hear more? Fine. Taking place over a decade ago, we follow Billy Crystal’s affable Harry and Meg Ryan’s particular Sally as they move to New York and go their separate ways, only to keep finding their way back to each other. The ultimate enemies-to-friends-to-lovers storyline, there’s a reason this is a classic. Full of witticisms, iconic scenes (“I’ll have what she’s having”), and a stellar supporting cast (here’s looking at you, Carrie Fisher, and Bruno Kirby), this movie never fails to make me smile. Need more convincing? This is the ultimate partnership between The Princess Bride director, Rob Reiner and romantic comedy queen Nora Ephron that feeds the romantic in you, while convincing the inner cynic to believe in love again. Honestly, there’s not much more I can say here given this film’s prominence in cinema, however this is definitely one that is worth checking out. Oh, and Chicago? Yes we are there briefly at the beginning, but this is really one of those New York City love stories that used to be famous between the ‘80s and ‘90s. Either way, you won’t be sorry. Trust me. (Alice-Ginevra Micheli)
A trip to Chicago seems like a perfect journey for a wayward musician to take to find a big solo break. Llewyn Davis felt the same as we take this journey with him in Inside Llewyn Davis, the downbeat and reflective musical drama from the Coen brothers. A perfect musical companion to O Brother, Where Art Thou?, Inside Llewyn Davis takes a sad and down-on-his-luck jerk at his lowest and pushes him into desperation. Filled with beautiful folk music (and one SILLY novelty song) and a knockout performance by the ever-talented Oscar Isaac, this Coen effort is an unsung entry in their illustrious filmography. A stacked cast of supporting turns bolsters Isaac’s Oscar-worthy performance as we see Llewyn take every chance he can to find his way back to musical success. Death, pain, and trauma haunt Llewyn’s past as he takes this sojourn to the office of F. Murray Abraham to perform an audition. It’s an emotional ride, culminating in one of the most emotionally raw scenes in any of the Coens’ work. (Shane Conto)
Surely, you can’t take someone seriously if they haven’t heard of the movie considered to be one of the funniest comedies of all time. What is it, you ask? It’s a humorous narrative, set to film, that runs for about 90 minutes, but that’s not important right now. If this is the first you’re hearing of this film, I find myself wondering if you’ve spent the last 40 years in a Turkish prison with a grown man, naked. I just hope that experience hasn’t resulted in a drinking problem for you. I don’t need to speak “Jive” to explain to you why this film is worth your time. But if this will be your first viewing, you picked a hell of a week to quit sniffing glue. When you do get around to it, I just want to tell you, “Good Luck, we’re all counting on you!” So find your seat, lock your tray tables in an upright position, grab your issue of “Nun’s Life” magazine, and make sure the autopilot is fully inflated, to enjoy Airplane! (Nick Ferro)
Based on a TV show from the ‘60s of the same name, The Fugitive released in 1993 to justifiable acclaim. Harrison Ford puts in a great turn as Dr. Richard Kimble, wrongly accused and convicted of murdering his wife. On his journey to prison, his transport is involved in an accident, and he manages to escape and go on the run. What follows is an intense set of circumstances that sees Kimble trying to find the real killer whilst being hunted by US Marshal Samuel Gerard (Tommy Lee Jones). The quality of The Fugitive was not lost on The Academy as itwas Nominated for Best Picture and Jones won for his supporting role at the 1994 Oscars. Filled with memorable scenes and lines, it eked its way into the social consciousness so much that even The Simpsons brilliantly parodied it. So if you have yet to see this modern classic, then search every gas station, residence, warehouse, farmhouse, henhouse, outhouse and doghouse in your area to ensure you see it ASAP. (Adam Ritchie)
Much like Butch Cassidy and the Sundance Kid, so much of what makes The Sting so enduringly great are the two lead performances of Paul Newman and Robert Redford. It’s either a shame or a great thing that these two never teamed up on anything other than the two aforementioned films, because while I would love to see eight more movies starring them and their natural charisma, I think the fact that we got two masterpieces made their team-ups that much more special. They play a couple of conmen in Depression-era Chicago in this film about how one small con gets them entrenched in a much bigger predicament than they ever intended to be. The Sting is full of tension and comedy and is dripping with so much charisma that some may have wiped off on you by the time you’re finished watching it. (Robert Bouffard)
North by Northwest is a great movie, masterfully directed by Hitchcock in one of his many “mistaken identity” tropes. Filled with ‘50s sensibilities, charm oozes from every frame. Stars aligned with the making of North by Northwest as this Oscar-nominated screenplay from legendary writer Ernest Lehman met Alfred Hitchcock at his peak era. Filled with cracking dialogue and dry humor, the screen smolders whenever we see our protagonist Roger Thornhill (played by screen legend Carey Grant) and the mysterious Eve Kendall (the stunning Eva Marie Saint). They simply don’t write movies like this anymore, and to be honest, I think we are better off for it so gems like this can be preserved in their full glory and remain untainted by direct copies and homages. (Adam Ritchie)
The Untouchables
When I was in high school, one of my best friends loved The Untouchables so much that he wrote and filmed (yes, I was also in it) in his own adaptation called The Unstoppables. We had so much fun making it, he screened it for his history class at our high school, and we took pride in the movie because it was a great crime movie and it was an iconic movie for those living in or around the Chicago area. This movie is the very definition of Chicago with its corruption, crime, and violence, but also features good people working for the greater good. Jim Malone (Sean Connery) said it best when it comes to Chicago: “They pull a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue. THAT’S the Chicago way!” The Untouchables features immortal characters who were larger than life in Chicago. Al Capone still holds a grip for people in Chicago with prohibition gangster era tourism all around the city. The Union Station staircase scene defines tension and is a familiar sight for movie lovers whenever people visit Chicago. I used to work in the Loop and I had lunch frequently at Union Station. Frequently when my coworkers and I would go by that staircase, there were people either taking pictures by the staircase or recreating that scene. Kevin Costner’s Eliot Ness and Robert De Niro’s Capone are great rivals and are putting on master classes in acting. I recently rewatched this and had forgotten how great it is. It made such an impact on me during the rewatch that it ended up making my top 100 movies of all time. (Mike Hilty)
Up in the Air
Up in the Air tells the story of Ryan Bingham (George Clooney) whose flies around the country basically firing people so those companies’ HR don’t have to. Ryan is called to his main office to be informed they are grounding flights and will be shifting to firing people remotely based on an idea from new comer Natalie Keener (Anna Kendrick). The movie travels through many cities and airports and shows how tough it truly is to have to lay people off. Director Jason Reitman does a fantastic job of showing real people in the opening and closing credits being fired as a way of setting up the stakes. Reitman also does a fantastic job blending the comedy and drama of the movie. It is stacked with incredible actors who chew the dialogue of this movie and makes you feel for these characters. If you have never seen Up in the Air, I love it and highly recommend checking it out. (Austen Terry)
The Big Sick
In the current era of film we live in, it isn’t often we see a well-received romantic comedy. In my opinion, that this is largely because the genre, like many others, have felt a bit overplayed and there is an overarching feeling of sameness that audiences don’t seem as interested in. That is unless the genre offers a slightly different perspective. In recent years, there have been a few rom-coms that have broken through and found appeal, and I think a lot of that can be attributed to the success of The Big Sick. This movie has the inherent advantage of being loosely based on the real story of Kumail Nanjiani and Emily V. Gordon’s marriage, but it also shows a very unique perspective to films that I personally had never seen before. It expertly marries the complex cultural conversations with incredibly funny dialogue and performances. It feels wholly fresh and original, thriving on the chemistry of Nanjiani, Zoe Kazan, Holly Hunter, and Ray Romano. I think it’s in movies like The Big Sick where the future of the romantic comedy genre lies, and I personally am very excited to see what is coming. (Nashua Doll)
The Trial of the Chicago 7
When it comes to screenwriters, there simply aren’t any better than Aaron Sorkin and it’s a very close list, but The Trial of the Chicago 7 is my favorite film of his. Going back to Sorkin’s wheelhouse with a courtroom drama, this time he takes the director’s chair as well. With a kinetic screenplay, clever editing moments (and one super clunky one), and an All-Star cast, The Trial of the Chicago 7 became one of the most watchable movies I’ve seen, just five minutes in. As the film progressed, I thought it is not only a technical achievement, but one of the most important stories that wound up being very timely with all the chaos that happened in 2020. This movie really does everything well and it is one I am constantly referring to other people, so if for some reason you have not checked this out, do it the next possible chance you can! (Aaron Schweitzer)
Source Code
When you say “Chicago,” what is the first thing you think of? That’s right, Source Code, the Jake Gyllenhaal sci-fi movie where he needs to stop the train from exploding, over and over again… right? No? Just me? Okay, it might be possible Source Code isn’t the first movie you are thinking when Chicago gets mentioned, but maybe it should. Because it’s still underrated, and dare I say underseen? Even though it stars the Jake Gyllenhaal, fan favourite of everyone who hasn’t read about him not showering too often. But that’s beside the point. Three years before Edge of Tomorrow made the Groundhog Day formula truly popular, there was this film that went about it in a different, more intriguing way. To the point when the movie is over, you are compelled to re-watch it, not just to fully understand it, but to enjoy it again, as it’s a great mix of sci-fi, action, drama, and bit of thriller in one shiny wrap (or in this instance, a train) coming your way. Maybe not “the most” Chicago movie ever, but one of the best ones of the last decade. Yeah, I said it. (Luke Burian)
Ferris Bueller’s Day Off
I have a challenge for you. Whip out your DVD copy of Ferris Bueller’s Day Off, select it from your Netflix queue, or hop in a time machine and rent the VHS tape from your local Blockbuster. If you can make it through the entire film without breaking a smile, I will personally fund every movie theater ticket, monthly streaming service fee, and physical media purchase for the rest of your life. Why am I so confident, you ask? Because it’s simply not possible. I defy you to keep a straight face when Ferris demonstrates his masterful clarinet playing (“Never had one lesson!”); or when Cameron offers his services in the form of a phone call to Principal Rooney (“This is George Peterson.”); or when Ferris spontaneously joins the Von Steuben Day parade with an impromptu, lip-synced rendition of “Twist and Shout.” Endlessly quotable, consistently hilarious and unexpectedly profound, Ferris Bueller’s Day Off is one of the most delightful films to grace this planet. You’ll be sure to leave the film with cheeks sore from smiling, but you’ll also leave the film with an appreciation for the smaller things in life. Take a note from Ferris (and countless high school grads who choose this line as their yearbook quote) when he says, “Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.” (Foster Harlfinger)
The Blues Brothers
They’re on a mission from God. Perhaps we can’t chalk it up to divine intervention, but the success of 1980’s The Blues Brothers is something that Saturday Night Live has tried to capture, and largely failed at, since their initial film. John Belushi and Dan Aykroyd star as Jake and Elwood, respectively, who seek to raise enough money to save the orphanage they were raised in by getting the band back together for a concert. The simple premise serves as the perfect setup for a multitude of fun musical numbers. The performances aren’t short on talent, including the likes of legends Ray Charles, Aretha Franklin, and James Brown. The musical numbers aren’t the only things that are well choreographed, like the infamous over-the-top chase scene where what looks like the entire Chicago Police Department chases the duo all around the city. Ridiculous doesn’t even begin to describe this film’s brand of humor. Carrie Fisher with a bazooka and some ticked off members of the Illinois Nazi Party are high points. If you’re in the mood for a ridiculous, fun ride, you’d be hard pressed to find a more star-studded option. (Jake Bourgeois)
Eight Men Out
Admittedly, I am not the biggest baseball fan and as a White Sox follower, it’s really hard to be a fan sometimes (but not this season). But there is something special to me about baseball films because you get to tell a much more grand story in a significantly less amount of time than your average baseball game. Eight Men Out is certainly no exception. Add to it that this is a period piece as well as a legal drama and it is a film that just feels like it was made for me. As a Chicago(ish) native, this movie really feels like a slice of life from my childhood: White Sox games, Chicago style hot dogs, and the thing Chicago is most known for: corruption. With an incredible cast and a clever way of approaching the story of the Chicago White Sox (at the time dubbed the “Black Sox” due to their tarnished reputation and the owner’s sleazy money saving techniques by not washing clothes), who threw the World Series in 1919, an excellent cast, and set pieces that really make it feel like we’re living in 1919 Chicago, Eight Men Out is a piece you should definitely seek out, even if you’re not a baseball fan! (Aaron Schweitzer)
A League of Their Own
I love a good baseball movie and A League of Their Own might be my favorite. The film tells the story of a pair of sisters that join the All-American Girls Professional Baseball League to entertain the masses during World War II as many Major League Baseball stars were pressed into service. It scratches both my nostalgic baseball itch and my history itch by telling me an unfamiliar story. The sisters, played by Geena Davis and Lori Petty, have a competitive rivalry that plays out throughout the film, but that’s not the only thing that holds our attention. The entire team, who we first meet at the league tryouts filmed at Chicago’s Wrigley Field, is fantastic. Madonna and Rosie O’Donnell are great as fellow members of the Rockford Peaches, Jon Lovitz is great in a supporting role, and Tom Hanks is brilliant as manager Jimmy Dugan. At this time (1992), Hanks’s star is about to explode and, in among his other roles, it’s possible this performance has become slightly underrated at this point. For lovers of both sports and history, this is a must watch. Throwing in an iconic Chicago landmark for this Cubs fan is just a bonus. (Jake Bourgeois)
Primal Fear
It seems to be something of a running theme for Edward Norton to play characters that are burdened with some sort of disorder or affliction that has them acting as if they have multiple personalities. Whatever you want to say about that in terms of portrayals of actual mental health issues, he’s quite adept at it by now. Primal Fear was his breakout role, playing young Aaron Stampler, accused of murdering an archbishop. Along with Norton and Richard Gere, the cast is littered with actors you’ll recognize, and focuses mostly around the trial to prove Norton’s character’s innocence by way of insanity. The city of Chicago features heavily, of course, with the focus mostly on the public outcry over the death of the Archbishop, and the coverups within the church and the authorities in Chicago. The movie itself is fairly middle of the road, but especially considering this was Norton’s first big performance, he elevates the material by quite some margin. (Chris Bakker)
Home Alone
It is a common myth that the first Saw film was released in 2004. In fact, it came out far earlier, in 1990. Your confusion can be forgiven, as the studio ran with the far more innocent title of Home Alone at the time. Despite its PG rating, this installment in the franchise is easily the most violent, rivaling A Muppet Christmas Carol for the title of the most violent Christmas film ever made. Years before Harry Potter, Chris Columbus gave us the story of another ungrateful child in Kevin McCallister, whose parents “accidentally” leave him solo in their abode while they enjoy a Christmas break to Paris. Good for them! Instead of being a burden to his parents, Kevin is forced to defend his family domicile from aspiring burglars Harry and Marv. Now, you may have noticed that I am being rather deliberately obtuse with the summary of this film. This is true, but believe me when I say that it comes from a place of pure love, spawned from, quite possibly, over 50 viewings of this classic. Framed by a whimsical, yet stunningly heartwarming, score, this is one of those Christmas films that is worth watching all year round. Following evil Laurel and Hardy as they haphazardly impale themselves upon Kevin’s house of horrors never ceases to entertain me, and always brings out bouts of schadenfreude induced laughter. However, I stand by the notion that Kevin is the true jerk of this movie, if for no other reason than wasting that highly nutritious microwaveable macaroni and cheese dinner. (Ian Whittington)
Candyman
Growing up as a kid in Northern Illinois, everybody knew about the film Candyman. In the ‘90s, besides our usual horror baddies, everybody seemed to remember him the most. Centered in the middle of Chicago’s notorious Cabrini-Green housing complex, a graduate student learns about Candyman, who kills his summoner after saying his name five times in the mirror. The jump scares and genuine horror still hit almost 30 years after its initial release. Candyman still holds strong. It’s grotesque, bloody disgusting, and keeps you on the edge of your seat. Tony Todd plays the titular character, with a bloody hook for a hand and a deep, gravelly voice that sends chills up your spine. For a film as old as Candyman, it still frazzles me. I still won’t utter his name in the bathroom, in front of the mirror. I dare you to say it. (Chantal A.)
Wanted
You know that Dr. Who quote, “I walked in universes where the laws of physics were devised by the mind of a mad man.” Well, I believe Wanted is a movie where the script came from the writers’ 14-year-old selves having a linked fever dream. I can see it now. Their minds goes, “assassins,” then the next one chimes in with, “and they can curve bullets,” the third one then chimes in and adds, “when they have target practice, they use real corpses they somehow acquired.” I don’t know whose call it was to have a magic loom be the thing that created the fraternity instead of supervillains coming together to kill all the superheroes and magic away all memory of their existence, but I don’t believe it was the right one. This movie is still great if you like cheesy action flicks with no sense of how physics actually work. Morgan Freeman departs from his usual good guy role to play Sloan, the leader of The Fraternity with Angelina Jolie’s Fox as his right hand. I really liked Fox because there was an effort to make her a whole person and have the plot react to her character instead of having her do things out of character just to make the plot go forward. There’s also a very young James McAvoy playing the main character of Wesley, who does all the main character stuff. (Kimberly Hausen)
The Whole Nine Yards
What would you do if you found out that your new neighbor was formerly a contract killer who faked his death? Well, The Whole Nine Yards answers this question as it tells the story of dentist Oz Oseransky (Matthew Perry) who lives in Canada with his wife, when one day a man moves in next door. This man turns out to be Jimmy “The Tulip” Tudeski (Bruce Willis) — a former hitman who rolled on the Chicago crime family he worked for and faked his death to move to Canada. Perry and Willis work very well together and play off each other very well, especially when the action starts to pick up. This action-comedy doesn’t get talked about enough or get enough love for its humor and story. It even has some exciting twists and turns, and if you haven’t seen it, it’s currently on Netflix, so check it out. (Austen Terry)
Transformers: Dark of the Moon
I’ve talked about Transformers movies here before and I will say, this one is great and it only got better with age, mostly because the following two films really bury the bar. Jokes aside, the battle of Chicago in the film is prime Bayfest mayhem. Many years before Avengers: Endgame, this film blew me through the back wall of the theater with the last hour being one long action sequence. In fact, now I’m going to have to watch it again because yes, I enjoy it that much. Until next time, kiddos, just enjoy movies. (Frank Kemp)
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