Sharper Seals Its Duplicity with Kiss after Kiss

Photo: courtesy Apple and A24.

Early on in Sharper, two romantic characters are gawking over a first edition copy of Jane Eyre in a bookstore set in the SoHo neighborhood of Manhattan. The woman asks the very simple question of, “Is it real?” The nodding yes she gets back isn’t convincing enough. She follows up with, “How can I be sure?” To that, the man leans in for a passionate kiss, the couple’s first. My, oh my! Nice move, young man. 

Pausing in that moment, wouldn’t it be amazing if all of life’s questions could be confirmed with mood-altering and knee-weakening kisses? That sealed kiss is also the first of many expected and unexpected ones in the movie that may or may not have truth, love, and conviction behind them. Greater than the smooches, that connected question of reality becomes the true orbicularis oris muscles of Sharper as it seeks to seduce us in mystery.

Two young people walk through a park.
Photo: courtesy Apple and A24.

Sharper is keenly broken into five chapters titled after characters in the movie. The first two sections cover the duo we see sharing that first kiss. Justice Smith (The Voyeurs) opens the narrative as Tom, the bookstore owner swept off his feet by the lovely NYU doctoral student Sandra, played by Briana Middleton of The Tender Bar. Over Japanese dinner dates, sunlit New York City strolls, and gentle pillow talk, the two become very close.

Matters hit a serious swerve when Briana’s unseen brother needs $350,000 to pay off a gambling debt, money that Tom is surprisingly able to provide easily. We (and Sandra) learn Tom comes from a wealthy family and is committed to help. However, the money and the woman turn the corner and disappear from Tom’s life, spiraling the jilted man to a new low of depression.

Lo and behold, the second chapter sheds light on where the seemingly perfect Sandra really came from. Dirtied up without refinement, she’s really a former junkie and parole violator who is acquired, of sorts, and groomed into an attractive co-conspirator of confidence schemes by the decadent and dangerous Max, played by Sebastian Stan. His larger target is Tom’s billionaire father Richard Hoobes (John Lithgow) and his new trophy wife Madeline (Oscar winner Julianne Moore). The taste of high society money is too good to pass up.

A woman and man sit on a couch apart in Sharper
Photo: courtesy Apple and A24.

Sharper’s second chapter on Sandra and third chapter on Max focus on creating the ideal con artist. Max propositions the beleaguered Sandra his goal to “teach you about everything so you can lie about anything.” It’s a slick little line and is pitted against the tenet that “You can’t cheat an honest man.” The indoctrination stage for Sandra in Sharper is fascinating and allows for some acting range from Middleton. 

As Sharper weaves double-crosses into triple-crosses and bags of cash meant for certain people to stay and others to go away are stuffed, it is up to the audience to determine who the honest ones are while the predatory presences lean, with years of practice, on their own mantra of “Never feel sorry for the mark.” The challenge for the viewer’s enjoyment is finding a character or position worth committing your allegiance towards inside the seedy decadence of fleecing the vain 1% crowd.

The best bet for that in Sharper is the dynamic between Briana Middleton and Sebastian Stan. Because of the split we see in Sandra/Sandy, we scoot forward to see what Middleton, the freshest face of the stacked cast, is capable of in the alluring department. The power of the movie’s trickery relies on her. Likewise, it is becoming a treat to see Stan, the hunky Marvel hero to many, tap into the sleazy-and-sexy mode he has pulled off so well in Fresh and Pam & Tommy over the past few years. Maybe the wildest card of the bunch is waiting for any kind of shoe to fall with the screen presence clout that comes with Academy Award winner Julianne Moore. The clashes to come are worth the spin. 

A hidden man listens to a kitchen conversation.
Photo: courtesy Apple and A24.

Needless to say, the doubts pile up quickly. To stretch out more plot directions would spoil further developments arranged by the team of prolific TV talent stepping up to feature films. Sharper is helmed by Benjamin Caron, who’s been slaying the small screen with high-profile stretches on Andor and The Crown. This collaboration with Apple and A24 stands as Caron’s confident feature debut. Granting him this knotty and simmering thriller are the Superstore and Comrade Detective writing team of Brian Gatewood and Alessandro Tanaka, who are returning to the big screen for the first time since 2011’s The Sitter. 

Calling Sharper an improvement from that forgettable Jonah Hill bomb is easy. Hopefully, Sharper’s embedded twists are not equally easy. Astute audiences will likely pick up on a few threads and call a few shots, but the volume of potential surprises is ample enough for the casual filmgoer. It just needs its chance to be seen in a weak February and hiding on AppleTV+.

Matching a line of threatening advice from Lithgow’s big fish, the aim of Sharper from Caron and company is quite high and rightfully so: “If you’re going to steal, steal a lot.” Frankly, a polished movie like this one, from the clean sets to the ominous Clint Mansell score, would have been relished in that fondly remembered mid-1990s marketplace of star-driven movies marketed for adults. Mature and malicious while skirting the line with a dash of kink, movies like Sharper don’t get made enough nowadays. Enjoy its casual boldness.

Written by Don Shanahan

DON SHANAHAN is a Chicago-based Rotten Tomatoes-approved film critic writing here on Film Obsessive as the Editor-in-Chief and Content Supervisor for the film department. He also writes for his own website, Every Movie Has a Lesson. Don is one of the hosts of the Cinephile Hissy Fit Podcast on the Ruminations Radio Network and sponsored by Film Obsessive. As a school teacher by day, Don writes his movie reviews with life lessons in mind, from the serious to the farcical. He is a proud director and one of the founders of the Chicago Indie Critics and a voting member of the nationally-recognized Critics Choice Association, Online Film Critics Society, North American Film Critics Association, International Film Society Critics Association, Internet Film Critics Society, Online Film and TV Association, and the Celebrity Movie Awards.

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