I Like to Watch | A Tale of Two Cities (with Dancing)
by Don Hall
My buddy Steve requested this piece. The concept of a work of art representing the city-as-character between New York City and Chicago—two world class towns in an almost relentless competition with each other—has a lot of possibilities. As I love Chicago with every ounce of me, the list of films that let the place shine in some ways is long. ‘The Fugitive,’ ‘About Last Night,’ High Fidelity,’ and ‘Barbershop’ all evoke some of the qualities of the city in slightly different ways while all still feeling fully Chicagoan.
Artists are inspired by it and its many facets because Chicago is not just a setting. It’s a supporting actor. A musical instrument. A damn mood. And the best Chicago movies know that. Arguably, I could say the following:
‘Chicago’ is the spectacle,
‘Ferris Bueller’ is the charm,
‘Hoop Dreams’ is the truth,
‘The Untouchables’ is the myth.
New York City has a similar cinematic love story to tell and be told. ‘Taxi Driver,’ ‘Do the Right Thing,’ ‘Annie Hall,’ and ‘In the Heights’ all paint pictures of NYC that only those enthralled by the city could create.
But the task presented is thus: ‘West Side Story’ is to NYC as what movie/story/musical is to Chicago? And my answer is simple because I’m on a mission from God.
When a city becomes more than a backdrop—when it becomes a pulse, a character, a co-conspirator in the narrative—you get a film that transcends location and becomes myth. In this way, “West Side Story” is to New York City what “The Blues Brothers” is to Chicago: not just a story set in a place, but a cinematic love letter that uses the rhythm, chaos, and contradictions of the city to fuel its very soul.
These aren’t travel brochures in film form. They’re operas of asphalt and attitude, musicals with cracked sidewalks and bruised knuckles, where characters sing not in the safety of sound stages but in the symphony of lived-in urban America. Each film immortalizes its city not by glamorizing it but by embracing its mess—its violence, its comedy, its ambition, its style.
“West Side Story” isn’t just set in New York—it bleeds New York. Specifically, the Upper West Side of the 1950s, back when Lincoln Center was still a bulldozed promise and entire tenement blocks were being razed in the name of “progress.” Its central conflict—between the Jets and the Sharks—is fueled by the demographic shifts and ethnic tensions that have defined New York since the Dutch showed up and declared it theirs.
The violence is choreographed, yes, but it’s also rooted in realism. The crumbling fire escapes, chain-link fences, and alleyway brawls aren’t decorative—they are New York. The stakes are life and death because the territory is real, the marginalization is real, and the characters’ need to claim space in an uncaring city mirrors the immigrant hustle baked into NYC’s very foundation.
“The Blues Brothers” does the same for Chicago, albeit in a different key—literally and figuratively. Here, the conflict isn’t racial gang warfare but civic absurdity, bureaucracy, and the struggle to do good in a city that eats good intentions with its toast dry. Jake and Elwood aren’t fighting for turf—they’re fighting to save a Catholic orphanage from foreclosure by pulling off a chaotic, illegal musical fundraiser. That sounds ridiculous. It is. It’s also deeply Chicago.
From parking tickets to Nazi rallies on the Dan Ryan to mall-destroying car chases, everything in “The Blues Brothers” is a joke with a kernel of truth: Chicago is a city of corruption, improv, faith, grit, and absurd persistence. It’s a place where systems are broken, but people keep showing up anyway.
So while “West Side Story” uses New York to stage its Shakespearean tragedy, “The Blues Brothers” uses Chicago to host a gospel-flavored farce. Both films, however, understand that their cities are pressure cookers—that identity, survival, and redemption can only happen in the crucible of concrete and steel.
Given both are filled with song and dance, it no surprise that the sound of each city is encoded in the two film’s musical DNA.
“West Side Story” is infused with Leonard Bernstein’s orchestral modernism and Stephen Sondheim’s razor-sharp lyrics. The music is jazz-inflected, percussive, complex, just like the city it represents. You can hear Manhattan’s clamor in the snapping fingers of the Jets, the salsa rhythms of the Sharks, the syncopated urgency of “America.” New York’s diversity, its chaos, its sophisticated danger—all of it lives in the score.
The characters don’t just sing because it’s a musical; they sing because New York demands it. You can’t survive in that town without shouting to be heard, and you can’t shout without rhythm. Even the tragic love of Tony and Maria gets drowned in the cacophony of class, ethnicity, and gentrification. Their voices may rise above the city but the city always wins.
“The Blues Brothers,” in contrast, is built from Chicago’s musical bedrock: blues, soul, gospel, and R&B. Not a traditional musical in the Rodgers and Hammerstein sense, the film breaks the fourth wall of logic and physics to stage full-scale performances by the likes of Aretha Franklin, Ray Charles, James Brown, and Cab Calloway. And each number is grounded in place: a diner, a church, a pawn shop, a street corner.
Chicago is in the chords. The soundtrack doesn’t try to impress with harmonic sophistication—it moves your hips and punches your chest. The musical moments in “The Blues Brothers” feel like Chicago in its Sunday best and its working-class worst, all rolled into one.
So where “West Side Story” is orchestral, balletic, and tragic—New York in a Tuxedo—“The Blues Brothers” is rowdy, sweaty, and swinging—Chicago in a wrinkled suit with scuffed shoes and a flask in the pocket.
Plenty of films are set in either place but are filmed in Toronto. These can still work but both films in this writing immortalize their cities by shooting on location, and those locations aren’t mere backdrops. They are characters that tell the stories alongside the narrative.
In “West Side Story,” the opening aerial shots of Manhattan establish dominance immediately: this is a city of vertical power and hard shadows. The film weaves through tenement rooftops, basketball courts, chain-link fences, and alleys—places where turf isn’t symbolic but strategic. It’s the myth of New York as a battleground where love tries and fails to exist. And while later adaptations leaned into soundstage stylization (see Spielberg’s 2021 version), the original grounds its tragedy in real brick and mortar.
“The Blues Brothers,” on the other hand, turns Chicago into a surreal funhouse mirror but the geography is real. They drive across the 95th Street bridge. They blast through the lower Wacker Drive tunnel. They stage a police chase through the Dixie Square Mall in Harvey. They even perform at the Palace Hotel Ballroom in Lake Wazzapamani (fictional, sure, but modeled after dozens of real Chicagoland venues).
More importantly, the film doesn’t sanitize Chicago. It celebrates the dirty snow, the blinking “L” trains, the rusted industrial skyline, the endless city bureaucracy. These details don’t support the story—they are the story.
Both films also tackle questions of identity (racial, cultural, and civic) through the lens of urban struggle.
“West Side Story” doesn’t tiptoe around the issue: the Sharks are Puerto Rican, the Jets are white, and the city is the arena of assimilation, colonization, and resistance. The musical wrestles with what it means to be American in a city that tolerates you but doesn’t welcome you. “I want to be in America,” sings Anita, with equal parts sarcasm and desperation. The city is opportunity and oppression wrapped together like a subway turnstile.
In “The Blues Brothers,” identity plays out more subtly but no less poignantly. Jake and Elwood are two white ex-cons wearing black suits and sunglasses, trying to “put the band back together”—a band composed almost entirely of black musicians. The film walks a fine line between appropriation and homage, and while some modern critics rightly ask tough questions, it’s hard to deny the film’s deep reverence for black musical excellence. These aren’t tourists—they’re acolytes.
The urban landscape in both films is a filter through which identity is tested. Whether you’re Puerto Rican in Manhattan or a soul singer in the South Side, the city both gives and takes. It forces you to define yourself against it—and in that struggle, art is born.
Ultimately, these films don’t just portray cities—they mythologize the urban journey as one of either redemption or tragedy.
“West Side Story” is a tragedy. Tony and Maria are doomed not because they fail to love, but because the city they live in refuses to change. The structures of hate, turf wars, and generational trauma are bigger than two teenagers with dreams. The final scenes are soaked in death, and the only redemption is Maria’s monologue—a plea for peace that hangs unanswered in the concrete air.
“The Blues Brothers” is a redemption arc wrapped in slapstick. Jake and Elwood are criminals, yes, but they are also on a “mission from God.” Their redemption is absurd, musical, and violent—they cause more property damage than any other film in history—but it’s heartfelt. They do the right thing the wrong way. In Chicago, that makes them saints.
Both cities, then, are unforgiving gods. In New York, love dies because the city won’t make space for it. In Chicago, salvation comes with collateral damage and traffic violations.
“West Side Story” gave us timeless standards like “Tonight,” “Maria,” and “Somewhere.” It won ten Academy Awards and remains the gold standard of urban musical tragedy. It became New York’s cinematic hymn, a snapshot of a city at war with itself.
“The Blues Brothers,” though less conventionally revered by the Academy, became a cult legend, especially in Chicago. The film has inspired everything from cover bands to live tribute shows to actual tourism. The mall chase, the “orange whip” line, the final crash into Daley Plaza—it’s all part of the city’s unofficial mythology now.
If “West Side Story” is Broadway’s version of New York—polished, tragic, brilliant—then “The Blues Brothers” is Chicago’s dive-bar gospel: chaotic, soulful, hilarious, and eternally underrated.
To say “West Side Story is to NYC what The Blues Brothers is to Chicago” is not to compare apples to apples. It’s to compare a symphony to a saxophone solo in a dive bar. Both are beautiful. Both are necessary. Both are true.
One gives us love denied; the other, redemption through rhythm. One mourns what the city takes; the other celebrates what the city gives. And both, in their own ways, elevate their urban landscapes to mythic status.
In these musicals, the city is never just a place.
In “West Side Story,” New York is a knife fight under a streetlamp.
In “The Blues Brothers,” Chicago is a church choir riding shotgun in a decommissioned cop car.
Both are unforgettable.
Both sing.
And neither could exist anywhere else.
