In the 1980s, Penthouse is at its height as one of the most successful magazines in America. Following the release of Bob Guccione's infamous Roman porno epic "Caligula," Penthouse faces a moral backlash from both the religious right and feminist left. Always keen to push boundaries, Guccione publishes nude pictures of the first black Miss America, Vanessa Williams, triggering a public outcry while sending sales skyrocketing.

As Penthouse enters the 1990s, the huge success of the magazine has led Bob Guccione to embark on a series of costly investments, including cryogenics and a casino in Atlantic City which is eventually sold to Donald Trump. Bob's youngest son Nick persuades his dad to let him branch out into video production. But the venture doesn't last and Bob pushes Nick out of the company which takes an emotional toll on Nick. Meanwhile Bob's relationship with his Penthouse 'Pets' takes a dark turn.

As Penthouse enters the 2000s, the magazine is in trouble. With sales falling, Bob Guccione pushes for the magazine to go harder against the advice of those around him, and Penthouse loses advertisers. Bob has pushed his three sons out of the business and taps his daughter Nina to help run the business as the age of the internet dawns.