32. Monica, "The First Night"
Although dueling teen divas Monica and Brandy spent the summer at Number One with their claws-out duet "The Boy Is Mine," they scored much livelier hits on their own. In "The First Night," Atlanta girl Monica dishes about her sexual prerogatives – "I wanna get down, but not the first night" – over a filthy disco bass thump sampled from Diana Ross' "Love Hangover," via her producer Jermaine Dupri. It wasn't the easiest year to be a one-named celebrity called "Monica" – the headlines were full of a certain stained blue dress – but she rode "The First Night" to Number One for five weeks. Monica went on to star in the BET reality show Monica: Still Standing and married NBA star Shannon Brown.