Exclusive: Britney Spears' Manager Tells the Story Behind the Infamous Madonna VMAs Kiss

According to Rudolph, "Madonna had been very, very, very rigid about the rehearsals. She was telling Britney and I every day, 'Be here tomorrow at 10 o'clock,' he tells Billboard. "She would never address me by name, she would just say, 'You make sure Britney's here tomorrow at 10 o'clock.'" Not wanting to upset one of the biggest stars of all time, Rudolph did his part.

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All that rigidity paid off. After the performance, Rudolph ended up in an elevator with Madonna, and it turns out she remembered his name. She "wrapped her arms around my waist and gave me a big kiss on the lips," he remembers. "And she said, 'You see Larry, it was all worth it.'"