The women involved in the strip club scheme that Hustlers is based upon are all very real, very complex characters. Destiny (Constance Wu) and Ramona (Jennifer Lopez), in particular, are stand-ins for real-life hustlers Roselyn Keo and Samantha Barbash, respectively, the two women at the center of a 2015 New York Magazine article, "The Hustlers At Scores," about their exploits swindling hundreds of thousands of dollars from rich Wall Street men. Part of the thrill of Hustlers, after all, is knowing that these events happened in real life.
Similarly, the way the con inevitably unravels in the film is also based on true events. In the movie, a customer named Doug [Bleep], played by actor Steven Boyer, goes to the cops not only with a story, but the evidence to back it up — leading to the eventual downfall of that particular strip club hustle.
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In real life, an anonymous strip club patron, referred to as "Fred" in the NYMag story, called into the New York City Police Department to file a complaint that he’d been drugged and had his credit card run up at a strip club (a claim that the police received often). Much of the circumstances surrounding "Doug" in the movie match "Fred" in the article (he lost his mortgage payment, asked Keo to give it back, found a way to prove they wronged him). The key, though, was that he had recorded evidence of what happened to him: in the NYMag piece, writer Jessica Pressler recounts how the man played a recording of a conversation he had with an unnamed perpetrator (also, exactly like the movie).
“I just want to know what happened to me,” he says on the audio recording, to which the woman on the other end of the line finally admits that he was “fleeced by a gang of ex-strippers who had spiked his drink with narcotics. Just a sprinkle.”
With that evidence in hand, the police tracked down the woman, likely one of Barbash’s associates, and questioned her about the strip club scheme. (See: the scene in Hustlers in which Madeline Brewer's Dawn gets brought in.) She told them pretty much everything, and agreed to help them with a sting operation meant to catch Barbash and Keo in the act. (See: Another scene in which Dawn wears a wire to one of the Hustlers' usual cons.) The sting operation ultimately failed, but not long afterward, a headline-making lawsuit caught the authorities’ eye and led them almost directly to the two women running the hustle. (See: Lopez's Ramona and Wu's Destiny being arrested and sent to jail.)
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But Doug/Fred/Anonymous wasn't the only guy who helped bring it all down. In April 2014, strip club Scores alleged that New Jersey cardiologist Zyad Younan had failed to pay a whopping $135,000 bill he’d racked up over the course of four visits to the club, and the New York Post picked up the titillating story. The police recognized the pattern from the previous man’s claims, and detectives launched an investigation. (In the movie, this role is filled by the architect who keeps trying to feel up Lili Reinhart's Annabelle upon first meeting her.)
By June 9, 2014, police had tracked down Barbash and arrested her at an ATM in her neighborhood, just like Ramona in the film. They then rounded up Karina Pascucci, the woman who had hustled Younan, and Marsi Rosen, another one of Barbash’s associates. They picked up Keo last.
The foursome was charged with forgery, conspiracy, grand larceny, and assault, among other things, which they all pleaded guilty to. Their punishment, however, varied greatly: Pascucci and Rosen served weekends in jail for four months with an added five week probationary period, while both Barbash and Keo managed to avoid jail time altogether; Barbash was sentenced to five years probation and Keo did not actually spend any time behind bars.
To this day "Doug" or "Fred" has remained out of the public eye, and kept his identity secret. Probably because as Lopez's Ramona jokes in the movie, men don't like everyone knowing they've been swindled by women. "What's he gonna say? I spent $5,000 at a strip club, send help?"