Where to even begin with Britney's infamous 2003 interview with Diane Sawyer? There's the fact that the veteran journalist asked the then-21-year-old intimate details of her sex life with ex Justin Timberlake. 'Now you're making me sad that I came because you're hurting my feelings,' she finally told Letterman after he rebuffed repeated attempts to change the subject, while the audience laughed at her expense.ġ5 Britney Spears on ABC Primetime - 2003 At first, she tried to laugh the questions off, but Paris became increasingly and visibly upset the longer the nearly 10-minute interview went on. 'How'd you like being in jail?' he asked a clearly blindsided Paris. Ahead of time, the talk show host had agreed to focus on the icon's business venture, but the moment she sat down, he started peppering her with mean-spirited questions about her time behind bars.
After spending two controversial weeks in jail that summer for a probation violation, the socialite mounted a comeback tour to promote her new fragrance, Can Can.Īs part of the media blitz, she agreed to appear on the Late Show with David Letterman. In 2007, Paris Hilton was at the height of her legal troubles as one of the most notorious It Girls in all of Hollywood. 2 Paris Hilton on the Late Show with David Letterman (2007)
