Paris Hilton along with her sometimes-partner in crime, Nicky -- is the heiress to the Hilton Hotel fortune estimated at $300 million, and was raised accordingly. Growing up the oldest of four siblings, Hilton moved between several homes, including a suite in the Waldorf-Astoria Hotel in her native Manhattan, Beverly Hills and the Hamptons. She attended schools in Manhattan, California and Conneticut and befriended the likes of Nicole Richie and Kim Kardashian along the way. As a child, she always craved the spotlight and began modeling at charity events before signing a contract with Donald Trump's modeling agency, T Management when she was 19. She's been affectionately making us cringe ever since.