29. Mariah Carey "Always Be My Baby" (1996)

Director: Mariah Carey
Album: Daydream

The Fresh Air Fund named a summer camp after Mariah Carey for all her support of the organization—specifically, using the backdrop of a lake and a tire swing as her set in the video for "Always Be My Baby," a story of young love. It's a dream sequence of two young kids sneaking out from their bunks at summer camp to escape to a campfire by the lake. Carey still sings, even while the kids party by the fire, in her ultra-'90s full-denim ensemble. -Lauren Nostro