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 when.

As Penthouse enters the 2000s, the magazine is in trouble; Bob pushes his three sons out of the business and taps his daughter Nina to help run things as the age of the internet dawns.