1) Paris Hilton
While Paris Hilton may have starred on The Simple Life, she certainly was not living the simple life in real life. Her party girl lifestyle started when she was a teenager living at Waldorf Astoria in New York City. She started going to clubs with her sister, Nicky Hilton. In the early 2000s, Hilton was everywhere and her partying was crazier. She has been arrested for a DUI and spent 23 days in jail. Hilton continues to be scene at all the newest hot spots with her always changing current fling.