I Want to Be a Hilton featured people who "Wanted to be like a Hilton." The finalist of the competition receives a prize package that includes a $200,000 trust fund, a new apartment, wardrobe and the opportunity to get to know the Hiltons. They resided at a fancy New York hotel and were divided into two teams, "Park" and "Madison". In each episode, they were required to perform certain tasks, ranging from dog grooming, a fashion show and organizing a charity event, while learning etiquette and manners. As they competed, Hilton guided them through a variety of challenges that cover subjects ranging from art and culture to beauty and fashion. Hilton met with the losing team at the end of each episode and eliminated one contestant with the catchphrase, "You're not on the list." The show was originally entitled The Good Life, to tie it in to Paris Hilton's reality show The Simple Life. The show was not renewed for a second season.

This documenary reveals the story behind the now-defunct "Park Avenue Peerage" blog. In the height of heiress-era NYC, an anonymous blogger infiltrated Manhattan's elite, bringing socialite celebrity to new heights, according to the doc’s logline. When the website's creator was unmasked, the mastermind was not who anybody expected.