Genre: Biography/Drama
Director: Damien Chazelle
Writer: Dwight Gallo
Cast: Andrew Garfield, Jesse Plemons, Felicity Jones, Adam Scott, Cuba Gooding Jr., Lili Simmons, Ashley Greene
Plot: Hugh Hefner (Andrew Garfield), a copywriter for Esquire magazine in Chicago, enters his boss' office to ask for a $5 raise. When he is denied, he quits and storms out of the building. He takes out a loan against his house, without telling his wife Millie (Felicity Jones), and goes to various investors with his friend Eldon Sellers (Jesse Plemons) to raise money to start his own magazine: Stag Party. However, he is soon notified that a magazine named Stag will sue him if he publishes his magazine with that title. Sellers suggests the name "Playboy".
Hef decided the selling point of the magazine needed to be a nude photograph of a woman. No matter how he crunched the numbers, he would not have enough money to hire a model to photograph themselves. Sellers tells Hef that he just heard that Marilyn Monroe had posed topless for a Chicago calendar photographer before she changed her name and became famous. With only $1,000 left in the budget, Hef is unsure if they'll be able to afford the photo, but when they go to see him, the photographer only asks for $600. Hef proceeds to haggle the photographer down to $500. Hef, Millie and Sellers produce the magazine in the kitchen of the Hefner home.
When Playboy hits the newstands, it's an instant success. Hef scrambles to produce enough copies of the magazine to send to news stands. One night Hef invites Sellers and his wife Janie (Ashley Greene) over. Hef, Millie, Sellers and Janie all watch a stag film together. Hef proposes to everyone that they sleep with eachother's spouses. Hef sleeps with Janie, but Millie backs out of sleeping with Sellers.
Now that they can afford to hire models for the magazine, Hef comes up with the idea of having a different model each month to be a centerpiece. Sellers suggests they call the model the "Playmate of the Month". Hef talks to art director Art Paul (Adam Scott) about coming up with some sort of logo for the magazine to help with recognition. Art comes up with several ideas, but Hef is immediately drawn to the idea of a rabbit. The logo debuts in the second issue of the magazine, which also sells well, proving the first issue wasn't a fluke. Hef and Sellers move the operations of the magazine to offices in downtown Chicago.
While the magazine continues to grow in success, Hef and Millie's marriage fails and the get divorced. Following the divorce, Hef reinvents himself as a man about town sort, frequently donning a silk smoking jacket with pipe in hand. He buys a mansion in Chicago where he throws numerous extravagant parties. He also opens a nightclub in downtown Chicago where the food and drinks are served by "Playboy Bunnies", many of whom are models for the magazine. Hef becomes well-known for his high-class lifestyle and for sleeping with many of his magazine's models. Hef, having established himself as a celebrity, begins hosting his own television variety show.
Playboy Magazine publishes a magazine that features Jayne Mansfield in bed with a man present. Authorities arrest Hef arrested on charges of selling obscene literature. He stands trial, with his defense team citing the freedom of the press guaranteed by the First Amendment of the Constitution. The criminal charges are dropped after the jury fails to reach a verdict. The trial does nothing to negatively affect Playboy's popularity.
Hef wants the magazine to be taken more seriously, so he hires Alex Haley (Cuba Gooding Jr.) to begin the "Playboy Interview" section of the magazine and interview various famous figures. These interviews help the magazine be taken more seriously by the mainstream media. Hef begins dating Barbi Benton (Lili Simmons), although he still sleeps with other women to maintain his image.
Hef decides to take Playboy Enterprises public, earning him enough money to purchase the new Playboy Mansion in Los Angeles.
Hef floats in the pool of the new expansive Playboy Mansion as countless nude playmates swim and play around him.
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