Ms. Jackson

While working on their fourth album, Stankonia, the Atlanta duo OutKast found one of its strongest songs taking shape at home. André 3000, one half of the group alongside Big Boi, recalled in Vibe that "Ms. Jackson" began as an acoustic guitar piece he had been playing in his house, which he then converted into something listeners could grasp more easily. The song drew on his relationship with the singer Erykah Badu and her mother, and its lyrics address the mother of the narrator's partner, examining the difficulties of having a child out of wedlock while promising to support the child no matter what happens. The track samples the Brothers Johnson's version of Shuggie Otis's "Strawberry Letter 23", treated with prominent reversing effects.

Released on October 24, 2000, as the album's second single, "Ms. Jackson" topped the US Billboard Hot 100 for one week on February 17, 2001, and reached number one in Germany, the Netherlands, Norway, and Sweden. Its success helped sell Stankonia after the lead single, "B.O.B", failed to chart on the Hot 100 despite wide critical praise. The song went on to win the Grammy Award for Best Rap Performance by a Duo or Group at the 44th Annual Grammy Awards.

Badu later admitted the song hit a sore spot for her, though she respected André's honest verse. Her mother, meanwhile, embraced it fully, buying herself a "Ms. Jackson" license plate, a mug, an ink pen, and a headband.