Kate Wolff joins Jon to discuss Britney’s iconic 1998-2003 run. They remember her wildest videos and live performances, the bizarre way the press treated her, and the electric Justin Timberlake relationship and breakup. They also weigh in on the Madonna vs. Britney debate, and we consider whether anyone utilized MTV as well as Britney. Kate also makes a compelling case directly to the Princess of Pop about why they should be best friends.

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