The music video to the song, which was filmed in February 1990 and was styled to resemble a 1930s and 1950s musical, featured Cyd Charisse, The Nicholas Brothers, and Cab Calloway in one of his last on-screen appearances. Anthony Thomas choreographed the video, with some scenes staged by veteran Hollywood choreographer Michael Kidd. The video begins with Jackson and two male dancers, including Richard Gaines, all wearing flashy zoot suits sitting on a bench. A paperboy throws newspapers on them. They wake up and read the frontpage of the newspaper, from which they learn Calloway is in town for the premiere of his Alright film. Jackson and her dancers take a cross-town journey to the premiere. There, Jackson, her dancers and Calloway fans wait for Calloway to make his grand entrance. Jackson seemingly envisions herself as Calloway's glamorized female guest, getting pushed to the red carpet. Calloway takes her hand and helps her up. Jackson and her dancers get in Calloway's limo. They arrive at large dance out in the middle of a street. Jackson and her dancers climb on the back of a car and Jackson notices her watch is missing. They get off the car and are sprayed by a street cleaning truck. They sit on the bench. Later that night, Jackson and her dancers are homeless people asleep on the bench—revealing the video to have been a dream. Cab Calloway, in the meantime, walks to the bench and places Jackson's watch in her hand. He sneaks away saying, "Alright". There is also an extended version that features rapper Heavy D. Jackson won a Soul Train Music Award for Best R&B/Soul or Rap Music Video in 1991.