43. Monica "The First Night" (1998)

Director: Joseph Kahn
Album: The Boy Is Mine

Monica isn't going to have sex with you right away, and her method of letting you will be elaborate. Hence, this video. "The First Night" was a No. 1 hit in America, and the supporting visual pushed forward the thought that Monica was the nation's new sweetheart. The dance moves were cute, the concept was simple, and it all came together perfectly in front of the camera. -Ernest Baker