There is something extremely maladroit about films set in Manhattan that center on really sweet automobiles. The majority of New Yorkers view the irrelevance of cars in their city as a bonus rather than a shortcoming, but many filmmakers still seem intent on having rich men in New York drive convertibles through Midtown Manhattan.

This discrepancy can be tolerated in certain venues, but in “August,” in which Josh Hartnett plays a smooth-talking dot-com hotshot trying to capitalize on the downfall of old media before the Internet bubble fully bursts, it is a strangely old-fashioned approach to the urban commute.

The mint-green 1969 Camaro driven by Tom Sterling (Mr. Hartnett) may be beautiful, but it undermines his ostensible place as the ultimate tech insider. Director Austin Chick (“XX/XY”) introduces us to Tom after a tryst in the bathroom of Bungalow 8, leaving the audience to ponder one thing as he drives away from 27th Street after a long night of partying: Don’t rich people move to New York City to avoid drunken-driving charges?

The smart ones, at least. And if Tom cares about one thing besides making money, it’s looking like a smart person. Throughout the film, though, small discrepancies like this one weaken his effort to mesmerize his peers and navigate his company into an earnings windfall.

Tom’s goal is to distract the market from his company’s dwindling bottom line. His pursuit of swank offices, expensive gifts, and jet planes is meant to inspire confidence in an uncertain time. But his bluff can’t hold for much longer. It is August of 2001. The tech prosperity of the 1990s is drying up, and the dot-com world is unaware that terrorists are about to send the Nasdaq sinking even lower.

Tom founded his company, Landshark, with his brother, Josh (Adam Scott). Like the film itself, Landshark is long on image and short on substance. But at the onset of “August,” the company is basking in the afterglow of an impressive IPO. Unlike the competing firms that have cratered into dot-com bubble free fall, Landshark has a mostly infallible plan for market dominance: No one, including Tom, seems to know what the company does.

As each passing day reduces Landshark’s stock price, Tom retaliates with increased decadence, drunkenness, and disparagement of his peers. He rants about all that is over and gives emphatic speeches on the power of “E”: “What you want is E. Pure E. Not E-commerce. Not E-business. Not click and mortar. Dear God, please not that. E. Not old, not tired, not stepped-on. Not one gram of E and 10 grams of baby laxative. Pure E.”

It may be the late 1990s, but Tom is not talking about Ecstasy; he’s talking about the powers of the Internet, and he does not appear to have any idea what he’s blathering about. Snide but earnest accounts of the importance of the Internet and how it will revolutionize the universe, without any attention to detail or context, seem to impress those around him, but the sermons have one little flaw. They are intensely comical.

Mr. Hartnett (egged on by screenwriter Howard A. Rodman) takes to his speeches with gusto, but he often lets on that some of the subject matter lies outside the reach of his vocabulary.

The dot-com era is rife with opportunities for satire, and “August” provides plenty — nonsense- speak about the tech boom, useless trinkets deployed as carpet-bombing branding, an influx of T-shirts under blazers. The touch point here is whether the filmmakers realize that they have constructed a cult of personality around an attractive windbag.

Tom can’t even choose the right woman after whom to futilely chase. Between meaningless flings, he is inexplicably drawn to Sarah (Naomie Harris), seemingly due to her strange accent and desire for him to show up on time for her events. Meanwhile, Melanie (Robin Tunney) struts around his office like a cat in search of a mouse to maul. As Landshark’s COO, she sucks the air from the room each time she enters, lusting after Tom while he muddles in a stupor of hungover adolescence, seemingly unaware.

At its core, “August” is covetous of Tom’s nonchalance, even as it undermines his business strategy. Woozy in its fascination with New York City, the film takes off running with Tom’s hipster aesthetic, but it leaves his plight comical where it should be serious, and glib where it aims for tragic.

When a corporate raider named Ogilvie (David Bowie) finally kicks Tom to the curb, it’s hard to muster up the sympathy the script requests. The dot-com era may only have been momentarily lush, but the moral was lasting: It’s hard to turn a profit when you don’t have a business model.