1. Date Night (2010)
In Date Night, milquetoast suburban New Jersey couple Steve Carell and Tina Fey make a disastrous decision to leave the womb-like comfort of their cozy hometown for a night in Manhattan, and discover that the city is a cesspool of sex, debauchery, perversion, corruption, and crime. It’s the latest in a curious cinematic subgenre: culture-clash comedies and dramas in which wide-eyed innocents, or at least reasonably normal, well-adjusted souls, get in way over their heads in nightmare-like metropolises that chew up and spit out gullible rubes on an hourly basis. In Date Night, Carell and Fey are pursued by crooked cops, get sexually propositioned on multiple occasions, destroy a car, uncover a sinister conspiracy, and generally deal with a whole bunch of fucked-up shit they’d never have to worry about if they’d stayed in their comfy little suburb.
2. Big Shots (1987)
In the fevered imagination of screenwriter Joe Eszterhas, innocence simply doesn’t exist. So it’s little surprise to find even an ostensible kids’ movie like his Big Shots teeming with grown-up corruption. Eleven-year-old Ricky Busker—a boy so naïve and soft, he’s like a live-action Ralph Wiggum—stumbles into an Eszterhas-standard harsh milieu when, in the midst of a hissy-fit over his father’s death, he accidentally runs away to Chicago’s south side, where he’s immediately robbed by a band of preteen thugs. Fortunately, he makes fast friends with the tellingly named Scam (Darius McCrary), a streetwise kid who carries a gun, hangs out in smoky blues clubs (where he orders Johnny Walker Red, no less), and hotwires cars for kicks. Their journey through Chicago’s mean streets finds them tangling with German hit men, baseball-bat-brandishing pawn-shop owners, and the kind of violence-inured sidewalks where kidnappings at gunpoint happen in broad daylight, all set to the dark strains of noted gutter-poet Steve Winwood. By the movie’s end, that unforgiving asphalt has scraped away the last vestige of Busker’s innocence, until he too has been tainted by the allure of petty crime and rakishly tilted fedoras.
3. Falling Down (1993)
It’s no wonder Michael Douglas’ tightly wound defense worker explodes with scattershot white-man’s rage: He lives in an EPCOT Center version of Los Angeles, all staged vignettes and broadly drawn stereotypes condensed into a Cliffs Notes’ read on inner-city tensions. Around every corner, Douglas stumbles upon a new symbol of L.A.’s boiling-over, riots-era anxieties—an overcharging Korean convenience-store owner, gun-wielding Hispanic gang members, the “not economically viable” black man loudly protesting his inability to secure a loan, a neo-Nazi shopkeeper, layabout Teamsters, privileged yuppie golfers, lazy beggars. Eventually they all cause Douglas to question, pointedly, “I’m the bad guy? How’d that happen?” Indeed, if only they could see what the city was really like, who wouldn’t blow up everything in sight with a rocket launcher?
4. After Hours (1985)
Few filmmakers are more identified with the life of the city than Martin Scorsese, which makes the farce After Hours an anomaly. Or maybe not, since it isn’t the city per se that’s threatening, but its bohemian downtown, where word-processor Griffin Dunne is lured in the hopes of scoring with Rosanna Arquette. What follows is a nightmarish odyssey is which Dunne’s character is pulled ever deeper into a bizarre underworld of threatening men and needy, damaged women, complete with Kafka-esque dialogues illustrating the futility of his attempts to make sense of it all. Given that Scorsese himself turns up shining a spotlight on Dunne in a suffocatingly hip nightclub, the movie makes most sense when interpreted as an attack on the paranoid solipsism of uptown dwellers.
5. The Out-Of-Towners (1970)
Like a comic version of Falling Down, the Neil Simon-scripted The Out-Of-Towners runs protagonists Jack Lemmon and Sandy Dennis through a gauntlet of indignities in New York reflective of the anxieties of the time: labor strife (mass transit, taxi, and sanitation strikes paralyze the city); rampant crime (they’re mugged twice and kidnapped by thugs after a botched holdup); social unrest (riots at the Cuban embassy); and the general rudeness that’s a timeless New York stereotype. Even a Good Samaritan mugs them (presaging a similar gag in Quick Change). Little changed in the lackluster 1999 remake starring Steve Martin and Goldie Hawn, proving that even Rudy Giuliani’s cleaned-up Big Apple can be a cartoonishly dangerous place.
6. Quick Change (1990)
In the underrated dark comedy Quick Change, Geena Davis, Randy Quaid, and co-director Bill Murray play bank robbers who pull off the perfect crime, only to discover that getting the fuck out of New York is more of a challenge than outwitting the police and bank officials. Dealing with surly bus drivers, con artists, incomprehensible cabdrivers, mobsters, thieves, and construction makes robbing a bank look easy by comparison. One thing is certain: After finally making their escape from New York, these cursed criminals are unlikely to ever come back.
7. Adventures In Babysitting (1987)
Chris Columbus’ 1987 movie Adventures In Babysitting is so similar to Date Night that Shawn Levy ought to be paying him royalties. But while sitter Elisabeth Shue and her underage charges’ introduction to the metropolis is a one-handed tow-truck driver with an itchy trigger finger, it turns out the city isn’t such a bad place after all. Sure, they get chased by a couple of mobsters in search of an errant Playboy, and wind up on stage at an all-black nightclub, where bluesman Albert Collins informs them “Nobody leaves this place without singin’ the blues.” But it turns out their suburban woes fit just fine over the 12-bar blues, and the audience ends up firmly on their side. They end up back in the ’burbs, but none the worse for wear.
8. Home Alone 2: Lost In New York (1992)
Consistently cited as John Hughes’ love letter to Chicago, Ferris Bueller’s Day Off also stands as a corrective to the “up with the suburbs” attitude of so much of Hughes’ filmography, even though it treats the city mainly as a suburbanite’s private playground. And while the Hughes-penned Home Alone proved that the fictional Shermer, Illinois could be just as terrifying as the big, bad city, nearly any location that Macaulay Culkin stumbles into in the film’s New York-set sequel is a dingy urban hellscape. (Well, unless it’s a five-star hotel or a well-appointed toy store.) The eternal Windy City-Big Apple rivalry is writ large across this negative portrayal of the city. And predictably, Joe Pesci and Daniel Stern’s revenge-crazed Wet Bandits blend in seamlessly with the city’s population of sharp-tongued cab drivers and leering prostitutes. Culkin eventually learns that the pigeon-covered woman in Central Park is a kinder soul than the snooty desk clerks at the Plaza, but first, he discovers that an under-renovation loft provides far more painful sources of slapstick burglar-torture than any suburban mini-mansion.
9. The Wiz (1978)
Diana Ross plays a young Harlem schoolteacher in the film version of the Broadway Wizard Of Oz adaptation, but she’s so wide-eyed and innocent that she might as well be from Kansas. Here, that shtick is necessary for her to convincingly play someone who’s from Harlem, but still gets blown away by seeing things like the World Trade Center plaza and/or a subway station. Unlike many films on this list, The Wiz is told from an African-American perspective in which the city becomes an all-devouring monster, out to eat the things that are best about its black residents. But between Ross’ strained performance and the garish production design and direction, the film is too much of a mess to make that idea interesting.
10. National Lampoon’s Vacation (1983)
Suburbanites through and through, Chevy Chase’s Clark Griswold and family aren’t any more at home in the country than they are in the city. (Even in suburban Chicago, he gets rooked by Eugene Levy as a sleazy auto dealer.) But their collective anxieties are never more pungently expressed than when Chase inadvertently detours into gritty East St. Louis, where his attempt to solicit directions from a fully decked-out pimp prompts a pungent “Fuck yo’ mama!” (Or, if you’re watching on network TV, “Who do I look like, Christopher Columbo?”) Shortly thereafter, their family truckster is swarmed by a gang of black men who relieve them of their hubcaps and spray-paint “Honky lips” on the wood paneling. For the most part, the scenes are staged to mock the Griswolds’ white panic rather than to rationalize it, but the sequence still vindicates the idea that no good can come from straying off the expressway.
11. Hardcore (1979)
In Paul Schrader’s brooding 1979 character study Hardcore, George C. Scott plays a deeply devout single father who ventures into the scuzzy Los Angeles porn underworld in an attempt to find his runaway daughter, who has traded in the security of upper-middle-class life in Grand Rapids for the sleazy world of porn films. The consummate square is forced to wrestle with the bleak reality that in the nasty city, his daughter became a colleague of disreputable folks with monikers like “Jism Jim,” and may have fallen in with a maker of snuff films. In the film’s most unintentionally hilarious sequence, Scott even dons a silly little mustache as he goes undercover as the world’s least convincing porn director.
12. The Brave Little Toaster (1987)
It turns out all our old appliances have feelings, and those feelings include “freaked the fuck out by big-city life.” This 1987 animated film kicks off when a toaster, a desk lamp, a radio, a vacuum, and an adowabul electric blanket realize they’ve been abandoned in the country home of a little boy—whom they call “Master.” Their search to find him takes them through all the elements, a creepy appliance store, and finally the big city where the Master is living. Upon arriving at his apartment, they’re forced to face two harsh truths: 1) They’ve been replaced by flashier, more powerful gadgets who can also talk, and 2) these fancy doohickeys are brash and intimidating, as city folk are wont to be. Even for inanimate objects, fear can be a powerful weapon.
13. Derailed (2005)
In spite of his marriage, Clive Owen in the 2005 thriller Derailed thinks he can duck into a hotel deep in the heart of the city for a little consequence-free nookie with sexy mystery woman Jennifer Aniston. He’s unaware that a few illicit moments of pleasure will nearly cost him his life. Owen soon learns that in the deep, dark city, extramarital sex is invariably punished with a vicious beating, blackmail, and the ever-looming threat of death, as sinister French hood Vincent Cassel and henchman Xzibit threaten to expose Owen’s clandestine affair. Owen could have spared himself a lot of hassle and heartbreak if he’d just joined a bowling league.
14. Havoc (2005)
Decadent, bored teen Anne Hathaway and best pal Bijou Phillips leave their wealthy homes for a little slumming in El Barrio in Havoc, a hysterical Kids-style cautionary tale of youth gone wild directed by Oscar-winning documentarian Barbara Kopple, and co-written by Oscar-winning Traffic screenwriter Stephen Gaghan and Jessica Kaplan, an L.A. teen who was only 17 when she sold the screenplay. Hathaway proves tough and resilient, but the deeply inebriated, naïve Phillips nearly ends up getting gang-raped as part of a gang initiation ritual, setting off a chain of events that leads to an armed confrontation between Hispanic gangstas and clueless white kids with too much testosterone and not enough common sense. All involved learn valuable life lessons, but not, alas, the kind that make for good college-entrance essays.
15. Into The Night (1985)
Also much like Steve Carell and Tina Fey in Date Night, depressed scientist Jeff Goldblum just wants a little jolt of excitement to shake up his otherwise-humdrum existence, but he gets a lot more when he encounters Michelle Pfeiffer fleeing bad guys in John Landis’ little-loved 1985 action-comedy Into The Night. Soon, the unlikely twosome are dodging the Iranian secret police and a British hitman played by David Bowie. Landis cast many of his filmmaking peers as the sketchy folks Goldblum and Pfeiffer encounter in their nightmare journey through the urban night, including himself as an Iranian henchman, makeup legend and frequent collaborator Rick Baker as a drug dealer, director Roger Vadim as a kidnapper, and Oscar-winning screenwriter Waldo Salt as a derelict.
16. Sunrise (1927)
As the cultural dominance of urban centers rose in the 1920s, movies like Fritz Lang’s Metropolis and Thomas Schadt’s Berlin Symphony envisioned the city as an inexorable machine in which humans played only an incidental role. In F.W. Murnau’s haunting masterpiece, that corruption spreads outward, as a dark-haired temptress identified only as “The Woman From the City” threatens the fragile marriage of George O’Brien and Janet Gaynor, convincing him to drown his wife so they can run off together. But instead, the husband balks, the wife flees to the city, and he follows suit. The city, so heartless in Murnau’s The Last Laugh, is a chaotic mass of speeding cars and hurried mobs, but it’s also the site of a church where the couple find renewed meaning in their marriage vows. Murnau’s expressionist metropolis, constructed via elaborate studio sets, is overwhelming, but not entirely without humanity.
17. Wet Hot American Summer (2001)
Anyone who’s been to summer camp knows that no matter how small the neighboring town is, it feels like a bustling metropolis by comparison with camp life, even if its entertainment opportunities consist of a Wal-Mart, a Culver’s, and that one weird porn shop with a giant grizzly-bear wood figurine out front. And as with other bustling metropolises, the potential for debauchery is high. The fabulous Wet Hot American Summer parodies that sentiment with a quick jaunt into town. The underage counselors engage in petty theft, struggle to secure a few beers, do hard drugs, get felt up by strange-old-man drug dealers, and come back to camp totally refreshed. Anyone who’s been to summer camp knows the drill.