Chicago, Chicago, You're My Kinda Town!
by scojofan | created - 24 Sep 2014 | updated - 01 Aug 2016 | PublicIn no particular order.
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1. The Blues Brothers (1980)
R | 133 min | Action, Adventure, Comedy
Jake Blues rejoins with his brother Elwood after being released from prison, but the duo has just days to reunite their old R&B band and save the Catholic home where the two were raised, outrunning the police as they tear through Chicago.
Director: John Landis | Stars: John Belushi, Dan Aykroyd, Cab Calloway, John Candy
Votes: 214,468 | Gross: $57.23M
2. High Fidelity (2000)
R | 113 min | Comedy, Drama, Music
Rob, a record store owner and compulsive list maker, recounts his top five breakups, including the one in progress.
Director: Stephen Frears | Stars: John Cusack, Iben Hjejle, Todd Louiso, Jack Black
Votes: 189,761 | Gross: $27.29M
3. While You Were Sleeping (1995)
PG | 103 min | Comedy, Drama, Romance
A hopelessly romantic Chicago Transit Authority ticket booth operator is mistaken for the fiancée of a comatose patient.
Director: Jon Turteltaub | Stars: Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle
Votes: 114,001 | Gross: $81.06M
4. Boss (2011–2012)
TV-MA | 60 min | Crime, Drama
Mayor Tom Kane, diagnosed with a dementia disorder, struggles to keep his grip on power in Chicago.
Stars: Kelsey Grammer, Connie Nielsen, Hannah Ware, Jeff Hephner
Votes: 18,360
5. Chicago P.D. (2014– )
TV-14 | 43 min | Action, Crime, Drama
Follows District 21 of the Chicago Police Department, made up of two different groups: the uniformed cops and the Intelligence Unit.
Stars: Jason Beghe, Marina Squerciati, Patrick John Flueger, LaRoyce Hawkins
Votes: 44,837
6. Save the Last Dance (2001)
PG-13 | 112 min | Drama, Music, Romance
A white midwestern girl moves to Chicago, where her new boyfriend is a black teen from the South Side with a rough, semi-criminal past.
Director: Thomas Carter | Stars: Julia Stiles, Sean Patrick Thomas, Kerry Washington, Fredro Starr
Votes: 65,968 | Gross: $91.06M
7. Three to Tango (1999)
PG-13 | 98 min | Comedy, Romance
A rich businessman's assumption that his new colleague is gay leads him to ask the man to keep an eye on his mistress. However, the man is not gay--and he begins to fall for the woman himself.
Director: Damon Santostefano | Stars: Neve Campbell, Matthew Perry, Dylan McDermott, Oliver Platt
Votes: 20,078 | Gross: $10.54M
8. Blink (1993)
R | 106 min | Crime, Drama, Mystery
Emma, a blind violinist who had recently undergone a revolutionary surgery, joins with a police detective to track a serial killer after she was an inadvertent witness to his latest crime.
Director: Michael Apted | Stars: Madeleine Stowe, Aidan Quinn, James Remar, Peter Friedman
Votes: 9,132 | Gross: $16.70M
9. Ferris Bueller's Day Off (1986)
PG-13 | 103 min | Comedy
A popular high school student, admired by his peers, decides to take a day off from school and goes to extreme lengths to pull it off, to the chagrin of his Dean, who'll do anything to stop him.
Director: John Hughes | Stars: Matthew Broderick, Alan Ruck, Mia Sara, Jeffrey Jones
Votes: 386,422 | Gross: $70.14M
10. About Last Night (1986)
R | 113 min | Comedy, Drama, Romance
A man and woman meet and try to have a romantic affair, despite their personal problems and the interference of their disapproving friends.
Director: Edward Zwick | Stars: Rob Lowe, Demi Moore, Jim Belushi, Elizabeth Perkins
Votes: 17,317 | Gross: $38.70M
11. The Chicago Code (2011)
TV-14 | 44 min | Action, Crime, Drama
Detective Jarek Wysocki, one of Chicago's toughest cops, struggles to clean up the town's violence and corruption.
Stars: Jason Clarke, Jennifer Beals, Matt Lauria, Devin Kelley
Votes: 8,481
12. Flashdance (1983)
R | 95 min | Drama, Music, Romance
An 18-year-old female amateur dancer who performs nightly at a dancing bar, and works as a welder during the day, dreams of joining the Pittsburgh ballet school.
Director: Adrian Lyne | Stars: Jennifer Beals, Michael Nouri, Lilia Skala, Sunny Johnson
Votes: 59,534 | Gross: $94.90M
13. Return to Me (2000)
PG | 115 min | Comedy, Drama, Romance
A man who falls in love with the woman who received his wife's heart must decide which woman it is who holds his heart.
Director: Bonnie Hunt | Stars: David Duchovny, Minnie Driver, Carroll O'Connor, Robert Loggia
Votes: 22,783 | Gross: $32.66M
14. Wicker Park (2004)
PG-13 | 114 min | Drama, Mystery, Romance
A young Chicago advertising executive believes a woman he sees in a café is his long-lost love. His belief leads to obsession, as he puts his life on hold in order to trail her.
Director: Paul McGuigan | Stars: Josh Hartnett, Diane Kruger, Matthew Lillard, Rose Byrne
Votes: 58,625 | Gross: $12.83M
15. Risky Business (1983)
R | 99 min | Comedy, Crime, Drama
A Chicago teenager is looking for fun at home while his parents are away, but the situation quickly gets out of hand.
Director: Paul Brickman | Stars: Tom Cruise, Rebecca De Mornay, Joe Pantoliano, Richard Masur
Votes: 99,830 | Gross: $63.50M
16. My Bodyguard (1980)
PG | 102 min | Comedy, Drama, Family
When a boy comes to a new school and gets harassed by a bully, he acquires the services of the school's most feared kid as a bodyguard.
Director: Tony Bill | Stars: Chris Makepeace, Adam Baldwin, Matt Dillon, Paul Quandt
Votes: 10,839 | Gross: $22.48M
17. The Break-Up (2006)
PG-13 | 106 min | Comedy, Drama, Romance
A couple's break-up proceeds to get uglier and nastier by the moment as each tries to keep their luxurious condo from the other.
Director: Peyton Reed | Stars: Jennifer Aniston, Vince Vaughn, Jon Favreau, Joey Lauren Adams
Votes: 138,979 | Gross: $118.70M
18. Only the Lonely (1991)
PG-13 | 104 min | Comedy, Romance
A Chicago cop must balance loyalty to his controlling mother and a relationship with a shy funeral home worker.
Director: Chris Columbus | Stars: John Candy, Maureen O'Hara, Ally Sheedy, Kevin Dunn
Votes: 12,343 | Gross: $21.83M
19. My Big Fat Greek Wedding (2002)
PG | 95 min | Comedy, Drama, Romance
A young Greek woman falls in love with a non-Greek and struggles to get her family to accept him while she comes to terms with her heritage and cultural identity.
Director: Joel Zwick | Stars: Nia Vardalos, John Corbett, Michael Constantine, Christina Eleusiniotis
Votes: 144,615 | Gross: $241.44M
20. The Lake House (2006)
PG | 99 min | Drama, Fantasy, Romance
A lonely doctor who once occupied an unusual lakeside house begins to exchange love letters with its former resident, a frustrated architect. They must try to unravel the mystery behind their extraordinary romance before it's too late.
Director: Alejandro Agresti | Stars: Keanu Reeves, Sandra Bullock, Christopher Plummer, Ebon Moss-Bachrach
Votes: 157,652 | Gross: $52.33M
21. My Best Friend's Wedding (1997)
PG-13 | 105 min | Comedy, Drama, Romance
When a woman's long-time friend reveals he's engaged, she realizes she loves him herself and sets out to get him, with only days before the wedding.
Director: P.J. Hogan | Stars: Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett
Votes: 155,384 | Gross: $127.12M
22. Never Been Kissed (1999)
PG-13 | 107 min | Comedy, Drama, Romance
A newspaper reporter enrolls in high school as part of research for a story.
Director: Raja Gosnell | Stars: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon
Votes: 97,556 | Gross: $55.47M
23. The Mob Doctor (2012–2013)
60 min | Crime, Drama, Mystery
A young thoracic surgeon becomes indebted to the South Chicago mafia and is forced to moonlight as a mob doctor, while also working full time at Chicago's most prominent hospital.
Stars: Jordana Spiro, William Forsythe, James Carpinello, Zach Gilford
Votes: 4,473
24. Public Enemies (2009)
R | 140 min | Action, Biography, Crime
The Feds try to take down notorious American gangsters John Dillinger, Baby Face Nelson, and Pretty Boy Floyd during a booming crime wave in the 1930s.
Director: Michael Mann | Stars: Christian Bale, Johnny Depp, Christian Stolte, Jason Clarke
Votes: 318,570 | Gross: $97.10M
25. The Color of Money (1986)
R | 119 min | Drama, Sport
Fast Eddie Felson teaches a cocky but immensely talented protégé the ropes of pool hustling, which in turn inspires him to make an unlikely comeback.
Director: Martin Scorsese | Stars: Paul Newman, Tom Cruise, Mary Elizabeth Mastrantonio, Helen Shaver
Votes: 93,256 | Gross: $52.29M
26. Source Code (2011)
PG-13 | 93 min | Action, Drama, Mystery
A soldier wakes up in someone else's body and discovers he's part of an experimental government program to find the bomber of a commuter train within 8 minutes.
Director: Duncan Jones | Stars: Jake Gyllenhaal, Michelle Monaghan, Vera Farmiga, Jeffrey Wright
Votes: 549,730 | Gross: $54.71M
27. The Untouchables (1987)
R | 119 min | Crime, Drama, Thriller
During Prohibition, Treasury agent Eliot Ness sets out to stop ruthless Chicago gangster Al Capone, and assembles a small, incorruptible team to help him.
Director: Brian De Palma | Stars: Kevin Costner, Sean Connery, Robert De Niro, Charles Martin Smith
Votes: 330,787 | Gross: $76.27M
28. Chicago Fire (2012– )
TV-14 | 43 min | Action, Drama
The story of firefighters and paramedics in the city of Chicago, both on a personal and professional level.
Stars: Taylor Kinney, Christian Stolte, Eamonn Walker, Joe Minoso
Votes: 64,552
29. ER (1994–2009)
TV-14 | 44 min | Drama, Romance
The doctors who work in the ER at the County General Hospital in Chicago grapple with ups and downs in their personal and professional lives while trying to give apt medical care to their patients.
Stars: Anthony Edwards, George Clooney, Julianna Margulies, Eriq La Salle
Votes: 67,729
30. Hoop Dreams (1994)
PG-13 | 170 min | Documentary, Drama, Sport
A film following the lives of two inner-city Chicago boys who struggle to become college basketball players on the road to going professional.
Director: Steve James | Stars: William Gates, Arthur Agee, Emma Gates, Curtis Gates
Votes: 28,016 | Gross: $7.83M
31. The Weather Man (2005)
R | 102 min | Comedy, Drama
A Chicago weather man, separated from his wife and children, debates whether professional and personal success are mutually exclusive.
Director: Gore Verbinski | Stars: Nicolas Cage, Hope Davis, Nicholas Hoult, Michael Caine
Votes: 83,311 | Gross: $12.48M
32. The Fugitive (1993)
PG-13 | 130 min | Action, Crime, Drama
Dr. Richard Kimble, unjustly accused of murdering his wife, must find the real killer while being the target of a nationwide manhunt led by a seasoned U.S. Marshal.
Director: Andrew Davis | Stars: Harrison Ford, Tommy Lee Jones, Sela Ward, Julianne Moore
Votes: 318,633 | Gross: $183.88M
33. Hill Street Blues (1981–1987)
TV-14 | 60 min | Crime, Drama, Mystery
The lives and work of the staff of an inner city police precinct.
Stars: Daniel J. Travanti, Michael Warren, Bruce Weitz, James Sikking
Votes: 10,563
34. The Loop (2006–2007)
TV-14 | Comedy
A recent college graduate adjusts to life as a corporate drone.
Stars: Bret Harrison, Eric Christian Olsen, Mimi Rogers, Philip Baker Hall
Votes: 2,018
35. The Chicago Code (2011)
TV-14 | 44 min | Action, Crime, Drama
Detective Jarek Wysocki, one of Chicago's toughest cops, struggles to clean up the town's violence and corruption.
Stars: Jason Clarke, Jennifer Beals, Matt Lauria, Devin Kelley
Votes: 8,481
36. Boss (2011–2012)
TV-MA | 60 min | Crime, Drama
Mayor Tom Kane, diagnosed with a dementia disorder, struggles to keep his grip on power in Chicago.
Stars: Kelsey Grammer, Connie Nielsen, Hannah Ware, Jeff Hephner
Votes: 18,360
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