Unfulfilled by family life and a desk job, Hugh Hefner strikes out against American puritanical values by launching a magazine that celebrates sex. He creates the first issue of Playboy from his kitchen table with the help of Marilyn Monroe as his first pin-up girl.

Hugh Hefner convinces his new subscription manager to pose as the magazine's first centerfold and the girl next door becomes Playboy's formula for success.

During the mid-1950s, Hugh Hefner and Playboy gain national success, giving Hefner an opportunity to speak out about social issues while enjoying the perks of being Mr. Playboy.

To bring Playboy's bachelor lifestyle to the public, Hugh Hefner opens the Playboy Club in Chicago and creates the perfect nightlife hostess - the bunny.

Hugh Hefner creates the Playboy Interview, giving a platform to cultural leaders to discuss pressing social issues, and publishes a controversial interview with Malcolm X.

Hefner becomes addicted to an amphetamine drug that lets him work around the clock, using the pages of the magazine to fight for civil rights and ultimately publish what would become Martin Luther King Jr's final written words.

While Hugh Hefner finds love and success in Hollywood, Playboy fights Penthouse in the pubic wars.

Hugh Hefner's secretary and close friend, Bobbie Arnstein, finds herself at the center of a conspiracy to take down the Playboy empire and her loyalty to Hefner proves deadly.

After the death of Bobbie Arnstein, Hugh Hefner retreats permanently to his Los Angeles mansion, only to face the murder of Playmate Dorothy Stratten.

With Playboy on the brink of bankruptcy, Hefner sacrifices friends and leans on family to secure the brand's future.