19. Mariah Carey: October 27th, 1990
Carey was just three years out of high school in Greenlawn, New York, when she hit the SNL stage. Dressed like she was on her way to the mall, the singer effortlessly performed a pyrotechnic version of her debut Number One hit, "Vision of Love," and the lung-bursting "Vanishing." She would play on the show three more times over the years, and cast member Cheri Oteri honored Carey with an impression in 1998.