In Orson Welles’ film noir masterwork, Touch of Evil, Welles' Quinlan is a rather large police captain with an empowering demeanor and a 30-year run of solving crime scenes and saving lives. Or so we’re led to believe. “Listen, I got a position in this town, a reputation...somebody's gonna be ruined,” Quinlan tells the all suspicious Miguel Vargas (Charlton Heston, strong makeup included) after planting some dynamite in an innocent suspect’s bathroom. As the plot unfolds and the drunkenly wavering Quinlan reveals himself to indeed be a fraud and a hoodlum, his close friends and confidants (Menzies) are left stunned rather than upset. They couldn’t believe someone this brazen and powerful could play the whole town, conveniently placed on the US-Mexican border, like a fiddle. After all, how could a guy this loquacious, wise and, dare I say, charming, fool everyone right under their noses?

Actor John Cusack has been playing a similar game of “what you see isn’t what you get” for audiences for multiple decades. Observing his “dark” turn in both The Paperboy and Maps to the Stars—a pair of independent films from the 2010s that now feel like a relic of the past— struck many critics as a surprising jolt of crazy. A new Cusack — unhinged and subversive. Affecting as he may be in those roles, Cusack’s always had that sinister dose of unruliness bubbling under the surface. His penchant for black clothing, followed by a laconic, top-of-the-morning’ like voice felt like a microcosm of 80s slacker indifference. Only more charming and introspective. To understand how we got the 2010s version of Cusack, it’s helpful to look back on how it all started. Namely, where it all started and how the daring actor’s 90s roles paved the way for more nefarious content later down the road.

Cusack had become a teenage heartthrob just a year earlier in Say Anything. What may now likely be seen as stalking, in 1989, blasting Phil Collins on a boombox outside your ex-girlfriend’s house was par for the course and heck, even romantic. What could’ve been just another teenage romantic comedy was augmented by Cusack’s quirks, like his kickboxing obsession and cut-off gloves. His casting in The Grifters, however, brought on a new test for the budding star as he had to learn the art of deception. The triple split screen opening scene shows Cusack, as Roy Dillon, sandwiched between his girlfriend Myra (played by Annette Bening) and his mother (Anjelica Huston). His suave strut morphs into a snakelike slippery as he approaches the restaurant bar. With country music playing over the scene, Cusack asks the bartender for a beer and flashes a $20 bill in the air for them to see —only to replace it with a $10 bill when the bartender comes to take the cash a few seconds later. It doesn’t take long to realize that this Cusack isn’t the sensitive oddball Lloyd Dobler type anymore. He’s now sporting a suit, slicked back hair, and a ratatat pattern of speech; always just three steps ahead of the next person he’s looking to grift.

“Who’s a boy to talk to but his mother?” Cusack remarks, clueing the audience in on the Oedipal relationship underlying much of the film. Despite more than holding his own in John Sayles’ Eight Men Out and working alongside Cameron Crowe in Say Anything, this film unleashed a markedly different energy. Stylized direction and cool, sleek performances. Cusack seemed to fit in seamlessly. He was less a caricature than a character, a walking, talking, con-man every bit in love with his mom as he is with Annette Bening. An offbeat Cusack was beginning to reel his head and the actor’s brash talking, Wellesian, noir sensibilities were marvelously on display for the first time in his young career.

The critical and Academy love shown for The Grifters furthered the notion that only was noir “in” (i.e. *One False Move, Red Rock West, and The Last Seduction all released shortly after) but that Cusack was now a bonafide leading man, fully graduated from the guy many fell in love with in the 80s. The next seven years would see an onslaught of box office duds, critical failures, and forgettable pictures for Cusack. Of the releases, only Bullets Over Broadway attracted any sort of audience or re-watchability factor while highlighting Cusack’s intellectual side. In 1997, Cusack finally landed a modest hit and returned to form in what I believe is his best work, in Grosse Pointe Blank.

Grosse Pointe Blank, his best movie, marked a point that assuredly hit Cusack’s sweet spot: black comedy meets romantic innocence. Cusack was now a bit older as he played a professional assassin returning to his idyllic hometown in Michigan for his ten-year high school reunion. In addition to bolstering a soundtrack that included a string of 80s hits, like Violent Femmes and David Bowie, the film served as an apt launching pad for the full spectrum of Cusack’s range: an actor who makes the transition between slick, ruthless killer vibes to deer in headlights naivete look seamless and immensely entertaining. Cusack’s Martin Blank was a character trying to find light in a world he’s only known to be dark and grim. Debi Newberry (Minnie Driver), Blank’s high school sweetheart who he stood up on prom night to join the army, seems to bring out Cusack’s best side while equally adroit at pulling no punches and needling or teasing Blank at all costs. The rest of the story is a tug of war match between Grocer (Dan Akroyd), a competitor assassin who sets out to kill Blank, and Debi, who is as much in love with Blank and he is with her.

What ages the film gracefully is the fact that Debi is a radio DJ for a local station, which Blank visits a few times to see her. No Cusack starring vehicle makes the actor’s cold-blooded killer streak feel as authentic and endearing as his flair for romance. The shot of Blank choking a crook out in his high school’s hallway is the perfect metaphor for the actor’s talents —someone stuck between child-like innocence and the need to inflict pain. The fact that Cusack plays Blank as a straight-man instead of over-the-top grounds the film with a sense of humanity is not otherwise seen.

“I just honestly don't know what I have in common with those people anymore... or with anyone, really,” Blank tells his therapist, Dr. Oatman (Alan Arkin), over the phone. This bit of on-the-fly therapy sessions appears throughout the film. “I mean, they all have husbands and wives and children and houses and dogs, and, you know, they'll have made themselves a part of something, and they can talk about what they do. And what am I going to say? ‘I killed the president of Paraguay with a fork. How've you been?’”

What Blank finds at the reunion strikes him most vividly when he holds up his ex-classmate’s months old baby in his arms. As Queen and David Bowie’s “Under Pressure” plays on in the background, the baby mouths a few words to Blank as he looks in disbelief that this creation could manufacture any sort of communication with him. The baby is a portal through an alternate life Blank could very much well be living though he chooses not to. To provide a healthy dose of nostalgia and gunplay is something only a combination of George Armitrage (director) and Cusack could muster. Though no film ever matched up with his one’s wit and tightness, Cusack found his wheelhouse with similar pictures in The Ice Harvest, he also did a good deal of genre hopping and worked with some name-brand directors in the following decade, including Clint Eastwood, Terrance Mallick, Spike Jonze, James Mangold and Harold Ramis.

Perhaps, then, what Cusack displays in The Paperboy shouldn’t come as a surprise. As with 1408, the actor’s interest in more brutal and suspenseful material certainly picked up and in Lee Daniels’ southern neo-noir sleazefest, Cusack plays Hillary Van Wetter, a small-time crony and alligator hunter on death row for killing a cop from stab wounds. Most of Wetter’s scenes come from the film’s main characters' visits to see him and extract information. What unfolds is Wetter, fittingly, wetting himself by getting off (without hands) to Charlotte Bless (Nicole Kidman) in front of three other people in the waiting room.

The scene is somewhat funny, even when Cusack’s Wetter is anything but. Wetter it’s quickly determined is a repugnant individual with crazed hair shooting out from the back of his head, as if he just spent many years numbed with pills at a mental institution. Cusack’s scratchy voice and his hypnotic, doe-eyed expression unearths something haunting and otherworldly. There is no humor to Cusack’s performance, he’s gone completely awry and fully committed to an ignoble cause. This also feels like a legitimate criminal and not Cusack’s imitation of one. The slow talking, epithet spouting, vile Wetter is unlike any role the actor took prior but it showed the fact that he too has range to explore as his age creeps up and Hollywood shuns him to VOD land.

Cusack continued to give another terrific performance in David Cronenberg’s Hollywood diatribe Maps to the Stars just two years later. Cusack, as Stafford Weiss, plays a TV psychologist with an impressive list of celebrity clients and a knack for exploiting them and others — think Tony Robbins meets Tom Cruise’ Frank T.J. Mackey in Magnolia — which almost makes sense given Cusack’s tendency to win audiences over by way of his buoyant charm in the decades prior. To make matters more awkward he’s also married to his sister (though he doesn’t discover that until many years later).

The film effectively reveals the toxic establishment seeping out and into the entertainment industry strata that pollutes the Tinseltown. For example, Cusack’s son plays a Bieber-like teen star and his wife Cristina (Olivia Williams) plays a zealous control-freak. As in The Paperboy, Cusack’s nefarious side transpires by way of unhurried movements, faceless expressions, unexpected beatings, and ghost-like, disguised home break-ins. There is no overacting or hysteria in Cusack’s Weiss, so when he becomes violent it comes as a shock and is imminently disturbing. Leave it to a director as prolific as Cronenberg to recognize that Cusack is, at this point in his career, less so an object of affection than he is a changed talent harboring untapped fury and diabolic proclivities.

To look back at John Cusack’s career in crime, black-comedies, and thrillers is to recognize that he had a dark side all along. Perhaps we, the audience, were the true subject of his Cusack’s con jobs and his winsome smirks. He, like Welles’ Quinlan in Touch of Evil, performed a massive feat of trickery in letting us believe that yeah he could kill or bankrupt a few people, but he was still the hero. Aside for High Fidelity and Say Anything, Cusack’s greatest talents were on display when he was able to get his hands dirty and play with the crime genre in a way intended by hard-boiled authors of the 50s and 60s. Martin Blank, for example, surely feels like a modern offshoot of guys that Jim Thompson or Donald Westlake would have written about. Making Grosse Pointe Blank stands in a class of its own.

To paraphrase Keyzer Soze: it’s not that Cusack’s greatest trick was convincing the world that his menacing side didn’t exist, but that his dyspeptic qualities could go so far in the other direction. As Cusack once successfully transitioned from teenage rom-com status to black-comedy and drama galore, so too he’s done it again the past decade. He’s become an actor willing to take bigger swings, tweak his career based on what’s offered, while never losing sight of that wry smile.

MATT BELENKY is a lawyer, Alanis Morissette enthusiast, reader of hard boiled crime novels, and a Coen Brothers devotee. His writing has been featured in Pittsburgh Orbit, Jedidah Ayres' blog, and on his website at www.thethirdtake.com.