Hilton and her sister, Nicky, are known for their jet-set lifestyles. Paris in particular has been trying to build herself into a marketable brand much like Donald Trump, claiming she must be regarded as a role model. She has been widely discussed by tabloids. In 2000, the National Enquirer reported a casual friendship with Leonardo DiCaprio as something far more intimate. She has also been linked with other young celebrities, including actor Edward Furlong, boxer Oscar De La Hoya, model Jason Shaw, Chicago Bears football player Brian Urlacher, and singers Rob Mills, Deryck Whibley, and Backstreet Boy Nick Carter.
In the fall of 2004, Hilton released a book, Confessions of an Heiress: A Tongue-in-Chic Peek Behind the Pose, which brings full color photographs of her and gives her tips on the dos and don'ts of living as an heiress. Hilton was reportedly given a $100,000 advanced payment for this book. Some in the media panned the writing as amateurish, and the book was parodied by Robert Mundell on The Late Show with David Letterman. Still, it became a New York Times bestseller.
The cover of the March 2005 issue of Playboy