18. Uncle Buck (1989)
It was right around this time that John Hughes gave up on high school confidentials and started backsliding fearlessly towards the womb: Uncle Buck> Home Alone>Baby’s Day Out.
This offering was a flop with critics and tends to polarize even Hughes most smitten fans. Even so, Hughes rides the undeniable charisma of John Candy to box office pay dirt and as usual puts Chicago and its north shore suburbs on loving display.
If you visit Hughes last resting place at the Lake Forest Cemetery in Lake Forest, Illinois, there is no mention of his film career anywhere on his monument. There is, however, a bronze statue of a fawn that appears to be dipping its head to nibble on the grass laid across Hughes’ grave.
That kind of innocence is what made some of Hughes filmography so great and so timeless. Whatever his blind spots as an artist: whatever the hell he saw in the young Macaulay Culkin, the unfortunate racial stereotype of the character of “Long Duck Dong” (gong sounds) in Sixteen Candles, Hughes got over on American film audiences in part, because the director was most definitely not a cynic.
19. Razor’s Edge (1984)
Only a few early scenes of this rickety Somerset Maugham film adaptation are set in the toney Chicago suburb of Lake Forest.
Doesn’t matter, this film’s inclusion on this list rests entirely on the strength of Wilmette, Illinois native and comic genius Bill Murray’s monologue paying tribute to fallen fellow Chicago area born comic gift, John Belushi.
Legend has it that Murray gave the same speech at Belushi’s funeral held at Martha’s Vineyard.
In the film, Murray’s character of Larry Darrel gives the speech after his coarse superior officer in the ambulance corps, played by Murray’s elder brother Brian Doyle Murray, falls on a WWI battlefield.
“He was a slob, did you ever see him eat? Starving children could fill their bellies on the food that ended up on his beard and clothes. Dogs would gather to watch him eat. I never understood gluttony, but i hate it. I hated that about you. He enjoyed disgusting people, being disgusting, the thrill of offending people and making them uncomfortable. You will not be missed. ” (Bill Murray as Larry Darrell)
20. Wayne’s World (1992)
This 1992 film would rank even higher in exquisite Chicago-mess if it actually wandered down the expressway towards Chicago proper a little more.
The film is technically set in the suburb of Aurora, Illinois and even spends some of its run time “up nort'” in Milwaukee “Algonquin for ‘The Good Land.” (Alice Cooper)
Despite these handicaps and the occasional palm tree appearing alongside the boulevards of Aurora, this is an inspired fourth wall perforating comedy with a pulsing Chicago heart.
Many of the film’s best scenes take place In a fictional donut palace owned by Chicago Blackhawks’ legend Stan Mikita and the film’s insanely talented star, Mike Myers, is an alumn of the Chicago based improv boot camp, Second City.
Though the performance of the film’s two leads, Myers and Carvey, are crucial to the success of Wayne’s World, movie is also chock full of interesting roles contributed by the film’s laundry list of veteran character actors.
The best of these supporting characters may be the unhinged donut shop manager played Ed O’Neill (Best known as the fictional Chicago based shoe salesman “Al Bundy” on the sit-com Married With Children) “I’d never done a crazy thing in my life before that night. Why is it when a man kills a man on the field of battle it’s called heroism, but if he kills another man in the heat of passion, it’s called murder?”
21. Child’s Play (1988)
Character acting treasure Brad Douriff (One Flew Over The Cuckoo’s Nest, Dune, Mississippi Burning and so on) voices “Chucky” a foul mouthed talking doll which houses the unclean departed spirit of a serial killer.
“Charles Lee Ray” (the aforementioned killer spirit that sets “Chucky” apart from other talking dolls on the market) sounds like a good ol’ boy’s name. That may be because a lot of good ol’ boys move north to Chicago looking for work. If one’s vocation is “killer” recent headlines affirm that a good sized city, like Chicago, has more bodies to stack than any downstate farming community.
The location shooting for “Child’s Play” was all done in Chicago and the city skyline, as usual, manages to look her part.
22. Eight Men Out (1988)
If there’s ever been a brilliant film about sports, this John Sayles directed love letter to the game of baseball might be it.
Yes, the book about the 1919 Chicago “Black Sox” scandal was better, because books are usually better, because a book isn’t hampered by budget or production schedule.
Despite the challenges presented in telling a story of such labyrinthian detail utilizing a relatively modest budget, indie stalwart Sayles (Brother From Another Planet) does an excellent of job of recreating the Chicago of a century ago, as well as making a believable Comiskey Park out of a decrepit old minor league stadium in Indiana.
The acting in the film is top shelf with Chicago natives John Cusack and John Mahoney acquitting themselves especially well in their respective roles as doomed third baseman, Buck Weaver( Cusack) and frustrated White Sox manager Kid Gleason (Mahoney.)
In addition to his directorial duties, Sayles steps in front of the camera to play legendary journalist Ring Lardner, to whom Sayles bears a remarkable resemblance.
23. Weird Science (1985)
One of the more lighthearted and entertaining takes on Mary Shelley’s Frankenstein story. Two pigeon chested high school misfits use their computer and a little help from NORAD to create Kelly LeBrock. In 1985, not a bad idea at all.
Though the occasional Cub hat and other “Land of the Onion Weed” (In Skree Indian its pronounced “She-Kah-Go”) artifacts are really the only clues we have that this film has any kind of Chicago pedigree. This movie, like most of the Hughes oeuvre, takes place in the fictional Chicago suburb of Shermer.
Watch for a cameo of Aussie character actor, Vernon Wells, reprising his mohawked biker of the apocalypse from 1981’s “The Road Warrior” during the film’s house party climax.
24. Robin and The Seven Hoods (1963)
The Rat Pack at the height of their alcohol and nicotine fueled powers play 1920’s Chicago gangsters. Plus, Frank Sinatra croons that Chicago is “My Kind of Town” and sure as shit sounds like he means it.
25. Risky Business (1983)
Utilizing a score by Tangerine Dream and fascinated with the ethereal beauty that is the Chicago skyline after night fall, this is somehow not a Michael Mann film.
Written and directed by Chicago born Paul Brickman, this darkly comic fantasy, which in someways functioned as the Polo and deck shoes generation’s “The Graduate” manages the nifty trick of making throwing down on an elevated train seem like a sexy, good idea. Just add young Rebecca DeMornay.
Author Bio: Jerimie Richardson is a newspaperman, bus driver, smart phone/ iMovie auteur and father whose heroes of letters are Minutemen lead singer D. Boon and long time Chicago newspaper columnist Mike Royko.