Americans are intrigued by charismatic con artists. From “Dirty Rotten Scoundrels” to “The Talented Mr. Ripley,” “Paper Moon” to “Catch Me If You Can,” there’s something enthralling about witnessing someone accumulate wealth by outsmarting others. These narratives subtly imply that attaining the American Dream is more accessible if you start with financial resources, crafting the con-man story as one of an underdog relying purely on charm and cleverness.

Why is Derek Cianfrance creating a con-man comedy? Renowned for his intense dramas like “Blue Valentine,” “The Place Beyond the Pines,” and “The Light Between Oceans,” which showcase serious actors like Ryan Gosling and Michael Fassbender, his newest endeavor is a romantic comedy featuring Channing Tatum and Kirsten Dunst. It’s inspired by a real-life con artist and convicted felon known as “Roofman.”

The unexpected shift in genre isn’t the problem; it’s that “Roofman” is baffling in its implementation. Following its debut at the Toronto International Film Festival, it’s uncertain whether Cianfrance has failed to craft a memorable con-man comedy or succeeded in critiquing the fundamental idea of the genre.

“Roofman” recounts the true tale of serial cat burglar Jeffrey Manchester. Between 1997 and 2005, the ex-U.S. Army Reservist targeted fast-food establishments and major retail outlets, breaking in through their roofs. Through voiceover, Jeffrey (Tatum) confesses to robbing 45 McDonald’s restaurants before being apprehended. In the film’s initial heist, he’s not merely an armed robber; he’s a “nice” one. He suggests the employees don their coats before locking them in the walk-in fridge, even offering one to the shift manager.

Jeffrey’s voiceover advocates for his actions, claiming he committed these offenses to provide for his ex-wife and children, glossing over the harm he inflicted. “Roofman” swiftly recounts his arrest, conviction, and early prison period. The film’s triggering event is his escape, filled with ingenuity and criminal artfulness. Now a fugitive, he finds refuge in a Toys “R” Us.

It’s a ridiculous premise that holds a degree of truth. While evading capture, Manchester forged new relationships, including a church-going girlfriend who knew him as John Zorn. Cianfrance’s second act ventures into romantic-comedy territory. A charming man entices a kind woman — single mother Leigh Wainscott (Dunst). They share flirtatious moments, enjoyable intimacy, and deep conversations about parenting and ethics. However, a sinister undertone lingers.

Is “Roofman” exonerating or critiquing Jeffrey Manchester? Tatum, recognized for roles in “Magic Mike,” “Logan Lucky,” and “21 Jump Street,” is a clever selection for Manchester. As John, Jeffrey captivates Leigh, her daughters, and church acquaintances, including Ben Mendelsohn as a pastor and Uzo Aduba as his spouse. Yet, Jeffrey’s charm is built on falsehoods regarding his identity, occupation, and living situation.

Numerous rom-coms depict a lie being revealed as a crucial moment that jeopardizes a happy ending. However, few involve glossing over violent offenses. As “Roofman” advances, Jeffrey’s allure and justifications become disquieting. He attempts to balance his actions by giving away stolen toys or assisting his girlfriend. The film raises doubts about whether Jeffrey can attain redemption or if he’s merely a self-deceiving fraud.

“Roofman” shifts to a darker narrative, surprising viewers of its cheerful promotional campaign. The romance with Leigh suggests Jeffrey merely needs a fresh start. But reconnecting with an old criminal associate (LaKeith Stanfield) and pursuing a Toys “R” Us manager (Peter Dinklage) indicates an impending escape.

With law enforcement closing in, Jeffrey makes a self-centered choice, leading to a climactic moment that dismantles the “polite” robber image. Nonetheless, the resolution softens with Leigh’s return. Exiting the theater, one ponders whether Cianfrance compromised the film’s darkness. Was the conclusion a feel-good resolution, or did it excuse Jeffrey’s misdeeds for the sake of entertainment?

The film’s closing credits feature the real Leigh and the pastor discussing John Zorn, blurring the boundaries between sin and crime. The takeaway isn’t about redemption but forgiveness. While Jeffrey may be the film’s focal point, he isn’t its hero.

Cianfrance utilizes the con-man motif similarly to how Jeffrey employs John Zorn, as bait for a different agenda. “Roofman” isn’t about a cunning con artist evading repercussions. Rather, it delves into redemption and the potential for misapplication. “Roofman” isn’t the delightful comedy or crime adventure its trailer implies. It’s darker, intricate, and leaves its message regarding con men and Jeffrey Manchester for the audience to interpret. Cianfrance steers clear of a straightforward conclusion, rendering “Roofman” a frustrating yet deliberate viewing experience.

“Roofman” made its debut at the Toronto International Film Festival and hits theaters on Oct. 10.