Leonard Smalls (Randall "Tex" Cobb), "Raising Arizona"
In the cult favorite "Raising Arizona," two lovable newlyweds are forced to deal with the consequences of kidnapping a baby. The scariest consequence is that the crime inexplicably awakens a ruthless bounty hunter named Leonard Smalls, who appears out of thin air to haunt both the husband’s dreams and his reality as the Lone Biker of the Apocalypse. In a madcap amalgamation of Mad Max and Road Runner cartoons, Smalls, played by former pro boxer Randall "Tex" Cobb, is introduced as a grizzly, leather-clad biker with mommy issues, more monster than man. The hyperbolic villain is an unhinged agent of chaos who takes joy in blowing up a rabbit with a grenade, shooting a lizard with a shotgun, and leaving a blaze of fire in his path. Despite being less a fully-realized character than a remorseless force of nature, Smalls indelibly embodies the anarchic spirit of the film.
Loren Visser (M. Emmet Walsh), "Blood Simple"
In their debut film, "Blood Simple," the Coen Brothers lay the groundwork for their wonderfully twisted love of eccentric characters. The film, which could have been a conventional take on infidelity, is complicated when the central love triangle is intruded upon by a private investigator, oozing sleaze and perpetually greased in sweat, played by the veteran character actor M. Emmet Walsh. Hired by Dan Hedaya’s cuckold to track and later whack his unfaithful wife and her lover, Loren Visser first appears to us in a bar, ominously blowing neon-lit smoke rings. As it becomes clear that he would rather get up to his own diabolical plans, Visser upends his initially minor characterization to wreak havoc on the entire picture. Visser anonymously haunts Frances McDormand’s Abby until the nerve-racking final showdown in a bathroom. With his fiendish last words soaked in macabre humor, Visser cements himself as the first of many dementedly intoxicating Coen Brothers villains.
Chet (Steve Buscemi), "Barton Fink"
As is often the case with Coen Brothers films, it is the most miniscule details that imbue "Barton Fink" with its infectious sense of eccentricity. As soon as Barton arrives to an empty front desk at Los Angeles' Hotel Earle, an uneasiness permeates the film and the hotel quickly begins to embody hell. Barton rings a bell that resonates for far too long until finally a bellhop, who goes by the name of Chet, comically emerges out of an unspecified underworld to hush the bell with his finger. Despite being jovial, Chet’s programmed responses and his peculiar pronunciation of "Los Angle-es" heighten the underlying creepiness of the setting. His exaggerated friendliness is punctuated by the exclamation point that follows his name on the note he hands to Barton. Throughout the rest of the film, Chet is an almost omnipresent background figure, patrolling the hallways and collecting shoes to be shined. While Buscemi would later famously be described as "funny looking" in "Fargo," the Coens’ first truly capitalized on Buscemi’s oddball charm with Chet.
Mike Yanagita (Steve Park), "Fargo"
Though chock full of unforgettable small parts that each deserve attention, "Fargo" produced one of the most awkward, puzzling and debated minor characters in the Coen Brothers film universe. As Mike Yanagita, Steve Park plays an ex-classmate of the film’s heroine, Marge Gunderson, who arrives for an unforgettable scene that does not serve the plot of the ongoing crime in any clear-cut way. When the two reunite, Mike is a little too touchy and overeager, but the scene becomes unbearably uncomfortable when he attempts to slide into the booth alongside Marge. When he reveals that his wife died of leukemia, things begin to make sense and miserable Mike momentarily wins our sympathy. That is until he frantically begins to declare his admiration for Marge as "a super lady." Only after the dinner ends does Marge learn that Mike fabricated the entire story about his dead wife, hinting at the reservoir of desperation and alienation that lies beneath the false fronts we put up.
Brandt (Philip Seymour Hoffman), "The Big Lebowski"
In terms of its minor characters, "The Big Lebowski" offers an embarrassment of riches, including none other than John Turturro’s pop culture phenomenon Jesus 'the Jesus" Quintana, but the real supporting winner is Philip Seymour Hoffman's Brandt, the Big Lebowski’s obsequious butler-cum-manservant. Hoffman was no stranger to elevating the smallest of roles and this was no exception. As the intermediary between Jeff Bridges’ Dude and his millionaire master, Brandt delivers some of the film’s most quotable lines ("This is our concern, Dude"). Somehow, Hoffman proved able to carve a character so smarmy that he flared his nostrils in rhythm with his labored laugh. Considering what a beloved character Hoffman made Brandt in a mere matter of minutes, it will forever be a shame that Hoffman was never able to reteam with the Coen Brothers.
Bernie Bernabum (John Turturro), "Miller's Crossing"
Like Loren Visser before him, John Turturro’s Bernie Bernbaum initially enters "Miller’s Crossing" as a peripheral figure, but soon seizes control of the narrative through the Coen Brothers’ daring, wondrously detailed characterization. Notably the filmmakers' first openly Jewish character, Bernie is a crooked bookie that ignites a full out gang war in Prohibition-era America when one mob boss demands his head. In the stand-out scene of the movie, a frenzied Bernie piteously begs for his life to Tom Regan, the film’s questionable moral compass, in an isolated forest. Turturro’s acting feat here is all the more impressive due to the range he displays both before and after this unforgettable scene. In his first appearance opposite Tom, Bernbaum displays his confidence, sitting back in his chair, calm and supercilious. Yet somehow when Tom reprieves him in the forest and tells him to leave town for good, we truly feel for Bernie, the pathetic weasel. But Bernie sticks around. When he arrives in the middle of the night in Tom’s apartment, Turturro showcases his versatility. Having regained his confidence, the two-timing Bernie seethes with menace and anger, telling the man who saved his life, "I want to watch you squirm." A multi-layered character for the ages, Bernie Bernbaum is a transcendent figure whose influence in the story is inversely proportional to the amount of time he is on screen.
Menelaus "Pappy" O'Daniel (Charles Dunning), "O Brother, Where Art Thou?"
Over the course of the odyssey of "O Brother, Where Art Thou?" the Coen Brothers introduce countless quirky characters that stumble into the path of the three escaped convicts at the center of the story, but perhaps the funniest is Charles Durning as Menelaus "Pappy" O’Daniel, the incumbent Governor of Mississippi. Durning, a terrific character actor who previously starred in the Coen Brothers’ "The Hudsucker Proxy," is at his best as the cantankerous, explosive politician who uses his repository of colorful dialogue to repeatedly snap at his son and his campaign managers. Unable to fathom how he is losing his votes to the dim-witted reform candidate Homer Stokes, O’Daniel lucks out when his opponent demands that the massively popular Soggy Bottom Boys be arrested. O’Daniel immediately jumps on the opportunity, taking to the stage uninvited to proudly dance alongside Ulysses Everett McGill, Pete and Delmar before belting out "You Are My Sunshine" to ensure his candidacy. As O’Daniel, Durning is the film’s comedic highlights.
Freddy Riedenschneider (Tony Shalhoub), "The Man Who Wasn't There"
After first teaming up with the Coen Brothers for "Barton Fink," in which he played the voluble movie producer Ben Geisler, Tony Shalhoub played another a fast-talker who likes nothing more than the sound of his own voice in the underrated noir, "The Man Who Wasn’t There." Here, Shalhoub plays Freddy Riedenschneider, a smug, big-city lawyer who delivers several delicious monologues. Between his extravagant hotel expenses and his gluttonous dinner orders, Shalhoub completely dominates every scene he is in, standing in stark contrast to the film’s reserved protagonist, Ed Crane, played by Billy Bob Thornton. In his most bombastic scene, Riedenschneider struts through expressionistic shadows to invoke Heisenberg’s Uncertainty Principle in order to exculpate his defendant on the basis of reasonable doubt. In spite of the blatant misreading of Heisenberg and his reductive logic, Riedenschneider is so self-satisfied by his words that it is hard not to get swept up in them.
Gas Station Proprietor (Gene Jones), "No Country For Old Men"
While "No Country for Old Men" is rightfully remembered for Javier Bardem’s merciless, bone-chilling Anton Chigurh, it is the face of one of his would-be victims that remains forever etched in our minds. At a remote Texas gas station, Gene Jones plays the elderly clerk on the receiving end of a menacing word game. The sad-eyed clerk is meek and harmless, a symbol of Southern hospitality, an analog to the Minnesota nice explored in "Fargo." When he asks, "Y’all getting any rain up your way?" Chigurh immediately responds, "What way would that be?" As it dawns on him that Chigurh is no "friendo," Jones’ expression gives way to an unforgettable blank stare. The ensuing moments are agonizingly tense as Chigurh prods the clerk into calling a coin toss, an arbitrary choice that will determine whether or not he lives or dies.
CIA Superior (JK Simmons), "Burn After Reading"
JK Simmons appears only twice in the Coen Brothers’ nosedive into black comedy, "Burn After Reading," but somehow he manages to steal the thunder from the inspired and outlandish performances delivered by everyone from John Malkovich to Frances McDormand and Brad Pitt. As an unnamed CIA superior, Simmons acts opposite David Rashe, a CIA officer who twice offers reports on the absolute mess our characters have made for themselves. Each of Simmons’ scenes unfolds after shocking acts of violence, which enriches the hilariously deadpan dialogue. Dumbfounded by the dumbness he hears, but also entirely unconcerned, Simmons briefly attempts to assign some meaning to the events by asking, "What did we learn, Palmer?" but it is clear that there is no lesson to the inanity of the human race and there is nothing left to do but turn the page. The chaos has sorted itself out, albeit in a bloody and illogical way, and Simmons’ resignation offers a fitting cap to the gloriously madcap misadventures that came before.
Mrs. Samsky (Amy Landecker), "A Serious Man"
Now starring on "Transparent," Amy Landecker first graced the big screen in "A Serious Man," the Coen Brothers’ ode to their Jewish upbringing in 1960s Minnesota. Landecker takes advantage of her limited screentime as Mrs. Samsky, Larry Gopnik’s dangerously sexy neighbor with a penchant for marijuana and Jefferson Airplane. Sunbathing in the nude, Mrs. Samsky makes quite the first impression, appearing to Larry from atop his roof. It is instantly clear that even though Gopnik should not get involved with her, he most certainly will. As Larry’s gateway to the counterculture, Mrs. Samsky later offers Larry to "take advantage of the new freedoms," which conjures up a dreamlike first encounter with drugs. In yet another memorable Coen Brothers dream sequence, this time set to "Somebody to Love," Larry makes strenuous love to Mrs. Samsky before a reverse shot reveals her taking a drag from a cigarette, entirely nonplussed. By somehow managing to make Mrs. Samsky both entirely blank-faced and devilishly alluring, Landecker offered quite the preview of her deft comic abilities.
Al Cody, (Adam Driver), "Inside Llewyn Davis"
Before he played Kylo Ren opposite Oscar Isaac’s Poe Dameron in "The Force Awakens," Adam Driver was an unexpected scene-stealer in "Inside Llewyn Davis" as Al Cody, a wannabe country singer. Conceived as a Jewish kid we later find out is actually named Arthur Milgram, Al at first looks like a fish out of water in his cowboy hat, but his sincerity during the performance of the hysterically hokey "Please Mr. Kennedy" is completely endearing. Over the course of the Cold War ditty, a visibly reluctant Llewyn plays guitar alongside a buoyant Jim, played by Justin Timberlake, and an ever-solemn Cody. As dorky the song is, it is mystifyingly catchy, striking a fine balance between believability and buffoonery. Driver sings in an odd, deep deadpan bass, adding unanticipated exclamations of "Uh-oh!" at the end of each line. His elongated pronunciation of “Outer Space” results in the most laugh-out-loud scene of the entire film, pure comic catnip.