The opening,of the script by Brian Koppelman and David Levien ("Solitary Man," "Oceans 13") with Timberlake's presence, suggest a somewhat less exceptional variation on "The Social Network's" focus on maverick entrepreneurialism in the Ivy League. Threatened with expulsion from Princeton unless he shuts his online gambling site, finance grad student Richie Furst (Timberlake), with nothing now to lose, heads for Costa Rica determined to stick it to the undisputed king of computer gambling, Ivan Black (Affleck).
Arriving during the boss's annual blowout, the Midnight Black Expo, Richie cleverly scores an audience with the bodyguard-festooned Ivan. Lounging on his hero's yacht, Richie and brazenly accuses him of cheating him on his site ... and Ivan readily admits it. In the film's best-written scene, Ivan affably agrees to reimburse the kid for his losses and then some — and then asks Richie if he'd like to come work for him. Seven, maybe even eight figures a year beckon.
With Puerto Rican locations doubling for Costa Rica, the allure of Ivan's world looks pretty tacky no matter how doused in money it is. With the help of a couple of other Yankee college boys who are given no character dimension whatsoever, Richie quickly learns the ropes and gets mixed signals from Ivan's glamorous factotum Rebecca (Gemma Arterton), who may or may not be on exclusive reserve for the boss. All goes swimmingly until, a third of the way in, Richie is kidnapped by none other than the FBI, whose local agent Shavers (Anthony Mackie) tries to coerce the kid into informing on Ivan's business.
When Richie tells his boss what happened, Ivan waves it off, claiming it happens to everyone who works for him. But Ivan has a little unpleasantness of his own in store for his eager acolyte, as he forces him to blackmail a top client into a continued business relationship, then starts using him as a bagman to pay off local authorities.
The overriding problem with the direction by Brad Furman ("The Lincoln Lawyer," "The Take") is that it lacks a real pulse, a throb of excitement that pulls you into this unsavory world and will accept no resistance. Furman stuffs the screen with luxurious digs, fancy cars, cool boats, private jets and parties loaded with scantily clad women, but there's no undercurrent, no intoxicating hook used to snare the audience, along with Richie, for the ride.
Finally, the drama's final stretch, in which Richie must desperately try to turn the tables on his boss if he has a chance of escaping with his hide intact, is dependent upon arcane financial and strategic moves that it is impossible to judge if it is realistic.