Hugh Hefner sold himself as a champion of free speech who created the Playboy brand to set off a sexual revolution that would liberate men and women alike, but over the years he used Playboy to manipulate women to compete for his favor and silenced whistleblowers.

In the 2000s, Hugh Hefner reinvented himself and his brand through the runaway success of the reality show "Girls Next Door," starring his girlfriends Bridget Marquardt, Kendra Wilkinson, and number one girlfriend Holly Madison. The series made mansion life seem like a fairytale, but Holly and Bridget reveal that the reality was a life full of rigid rules, gaslighting, and infighting.

The Playboy Bunny was the most famous sex symbol of the 20th century. Playboy hired the most attractive women in the world to don the ears and tail by promising an environment where they would always be protected. But outside of the clubs, at the Playboy Mansion itself, and in the company of Hefner's VIP customers, the Bunnies faced dangers and abuses that were covered up by the Playboy "cleanup crew."

This episode explores the 1970s DEA investigation into Hefner, Playboy, and drugs through the lens of two women who lived and worked at Playboy: Hefner's right-hand woman Bobbie Arnstein, who died by suicide while being investigated for drug trafficking, and Playboy Bunny Adrienne Pollack, who died of a drug overdose in 1973.

After decades of silence, Hefner's former number one girlfriend Sondra Theodore shares her story detailing how she was groomed by him to participate in his increasingly abusive sex life. Sondra's testimony shines a spotlight on Hefner's mechanisms for controlling and breaking women.

The Playboy corporate world was billed as a welcoming place for women, but Playmate and eventual Director of Playboy Promotions Miki Garcia and Bunny Mother PJ Masten reveal the rampant sexual harassment they faced as they attempted to climb the corporate ladder.