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20 Chicago movies and TV shows on Netflix

"On Wednesdays, we wear pink."
Image: Mean Girls/Facebook "On Wednesdays, we wear pink."

Chicago will never keep up with Hollywood's film industry precisely because it doesn't want to. Films set in Chicago have a grittiness and dark humor that often gets airbrushed away in West Coast film studios. To be sure, Chicago also has a softer side. A shocking number of romantic comedies are based in the city, including My Best Friend's Wedding, which kickstarted Julia Roberts's ascendancy in the genre, as well as the more recent Drinking Buddies starring both Olivia Wilde and Anna Kendrick. 

What unites all films based in Chicago is their frankness. Whether it's in humor (Mean Girls), hard truths (Hoop Dreams) or even outright criticism (Chicagoland), this city's movies remain honest in a way the coast's have failed to replicate. Here are 20 you can currently find on Netflix:

Movies

The Blues Brothers

What began as a Saturday Night Live sketch by Dan Aykroyd and John Belushi could not be contained. After only three appearances on the show, the duo released an album and two years later starred in this iconic film of car chases and the blues, featuring performances by Aretha Franklin, James Brown, Ray Charles and John Lee Hooker.

Drinking Buddies

Those who’ve been on the brewery tour at the Revolution Brewing Taproom will recognize the workplace of the two main characters Kate (Olivia Wilde) and Luke (Jake Johnson). Realistically, the plot is everyone’s worst nightmare: falling in love with your co-worker and best friend when you’re both already dating someone. Throw in a trip to a cabin in the woods and things get positively complicated.

Ferris Bueller’s Day Off

Do we really need to explain one of the city’s best fictional Chicagoans? Well, it stars a young, strapping Matthew Broderick as one Ferris Bueller, a rowdy teenager who plays hooky with his friends to romp around Chicago. This is definitely one must-see film for all in the city.

Happy Christmas

Anna Kendrick stars in this dramatic comedy as a young woman named Jenny, fresh off a breakup, who moves in with Kelly, a writer, her pianist husband and their 2-year-old son. Jenny and her friend Carson (Lena Dunham), shake up the family’s domestic life and force Kelly to redefine what it means to be happy in her life and profession.

H.H. Holmes: America’s First Serial Killer

As the title informs us, Chicago’s very own H.H. Holmes is infamous for being the first known serial killer in the U.S. Holmes was so dedicated to the act of killing that he built a three-story, one-block hotel for the purpose, which was open during the 1893 World's Columbian Exposition. Holmes confessed to 27 murders, but there may be as many as 200. This chilling documentary tells the story of Holmes, his killings and the “murder castle” he built.

Hoop Dreams

This documentary follows two African-American boys and their quest to become professional basketball players while growing up in Chicago’s inner city. It was one of the relatively few films beloved Chicago film critic Roger Ebert gave four stars, and it won the Audience Award for Best Documentary at the Sundance Film Festival when it premiered in 1994, as well as a slew of other prestigious film honors.

Mean Girls

There’s some debate over whether Tina Fey based the cliquish North Shore High School, where new girl Cady meets the Plastics and learns to wear pink on Wednesdays, on Evanston Township High School or Winnetka’s New Trier High. Getting a definitive answer, much like “fetch,” isn’t going to happen. Watch to remember there was a time when Lindsay Lohan could play a naïve innocent.

My Best Friend’s Wedding

This 1997 romantic comedy was the beginning of Julia Roberts’s dynastic takeover of the romantic comedy genre. In college, Julianne (Roberts) and her friend Michael promise one another they’d marry if they weren’t hitched by age 28. Then Michael calls Julianne two weeks before her 28th birthday to tell her he’s getting married to Kimmy Wallace (Cameron Diaz). Julianne heads to Chicago to sabotage the marriage.

Only the Lonely

It seems almost every extremely famous comedian has done a romantic comedy at some time in their career, and John Candy is no different. This one has him playing a 38-year-old Chicago cop who still lives with his very strict, very Irish mother and falls in love with introverted funeral home worker.

Planes, Trains & Automobiles

Another Chicago film starring John Candy, this time he’s paired with the slapstick hijinks of Steve Martin. Martin plays Neal Page, a stressed out marketing executive just trying to get back to Chicago, while Candy plays Del Griffith, who’s an almost irritatingly extroverted shower curtain ring salesman. After meeting, the two embark on a three-day journey trying to get Neal home from New York City so he can have Thanksgiving Dinner with his family.

Risky Business

Before Tom Cruise truly fell down the Scientology wormhole, there was a boyish series of films that Risky Business belongs to. Cruise stars as Joel, a rowdy teen who has been waiting for his parents to get out of town and gets into loads of trouble when they do. The film features one of the most iconic scenes in 1980s cinema, with Cruise dancing in a snug pair of tighty-whities and a button-down as he glides across the hardwood floor in a pair of brand new socks.

The Weather Man

Nicolas Cage does some great wallowing in this surprisingly dark film about a Chicago weather man named Dave and his midlife crisis, filmed in part in locations in and around Chicago. Watch for Dave’s West Loop apartment and scenes in and around Belmont Harbor, Evanston and Skokie. Oh, and Michael Caine is in it too.

While You Were Sleeping

Sandra Bullock, another queen of romantic comedies, plays Lucy, a CTA fare collector (in the era before Ventra) who’s secretly fallen hard for Peter, a daily commuter she’s barely spoken to. One day, she rescues him from an oncoming train after muggers push him on the tracks. Despite this, Peter falls into a coma. When she visits him in the hospital, a nurse introduces her to Peter’s family as his fiancée, and she doesn’t deny it.

TV Shows

The Boondocks

Young and black, Huey Freeman and his family relocate from Chicago proper into the undeniably white suburban landscape that surrounds the city. The Boondocks began as a comic strip and received critical acclaim when it was produced for television. The show tackles issues surrounding modern-day society and black culture and is known for being divisive and unapologetic, finding a perfect home on Cartoon Network’s Adult Swim programming.

Boss

Kelsey Grammer (yes, Frasier himself), plays Chicago mayor Tom Kane who is diagnosed with a degenerative neurological disorder. Kane hides his dementia from his wife, his co-workers—everyone but the doctor who diagnosed him—but slowly clues slip through the cracks to his friends and enemies.

Chicagoland

This Robert Redford-produced series originally aired on CNN. The eight-part documentary centers on the contentious decisions of the Rahm Emanuel mayoral administration over Chicago, such as CPS school closures, the use of city funds for Navy Pier improvements and the prevalence of mass shootings.

The Crazy Ones

It’s a shame this comedy series was filmed in Los Angeles, because The Crazy Ones was the last time Robin Williams would "return" to Chicago onscreen. In the show, Williams plays Simon Roberts, who runs an ad agency with his daughter Sydney (Sarah Michelle Gellar). The story is loosely based on the life and career of John R. Montgomery, an ad executive who spent more than 30 years at Leo Burnett.

Sense8

Sense8 is the brainchild of Andy and Lana Wachowski, the duo behind The Matrix and directors of Cloud Atlas. This Netflix original show explores much of the same themes, centering on strangers strewn across different parts of the globe who are suddenly mentally and emotionally linked and must survive people who are hunting them down. The first season premiered in June and a second is on the way.

The League

Chicago is the logical setting for a show all about a fantasy football league. While FX’s winning sitcom isn’t actually shot in Chicago, much of the action takes place at our own Gibsons with appearances by Matt Forte and Jay Cutler. This show is as much for comedy nerds as football fans with an ensemble including Nick Kroll (Kroll Show), Paul Scheer (Human Giant) and multi-talented Mark Duplass.

Shameless

Almost, but not quite. This is the British original that did it first before Shameless was brought to Chicago by Showtime. Expect much of what you’re used to from the American version—similar plot twists, characters and story developments, but a new set of actors playing this dysfunctional family.

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