Ms. Jackson – OutKast | Top 40 Chart Performance, Story and Song Meaning

UPDATED:Apr 14, 2026 6:46 PM
POSTED:Apr 14, 2026 5:43 PM

Chart Performance: Pop (#1) and R&B (#1); 2000

Story Behind The Song By Harris Sterling

In 2000, OutKast released Ms. Jackson as the second single from their album Stankonia. Written and produced by André 3000 and Big Boi, the track became the duo’s first #1 hit on the Billboard Hot 100.

The song was inspired by André 3000’s relationship with singer Erykah Badu and, specifically, his desire to address tensions with the mother of a former partner. Rather than direct confrontation, the lyric takes the form of an apology and acknowledgment of shared responsibility.

Released in late 2000, Ms. Jackson climbed to #1 on both the Hot 100 and the R&B chart. Its success expanded OutKast’s mainstream audience while maintaining their distinctive Southern hip-hop sound.

Built around a crisp drum pattern and melodic hook, the production balanced rap verses with a memorable sung chorus. The lyric reflects on the complications of relationships and parenthood, delivered with candor rather than defensiveness.

Ms. Jackson won the Grammy Award for Best Rap Performance by a Duo or Group and remains one of OutKast’s signature recordings.

Produced by:
André 3000
Big Boi

Lyrics Written by:
André 3000
Big Boi

Awards:
Grammy Award for Best Rap Performance by a Duo or Group (2002)

Harris Sterling

Harris Sterling

Independent music label executive Harris Sterling has worked in the music industry for most of his career.

As Executive Vice President for independent music label Madacy Entertainment, he led the strategic marketing and business development for the label, negotiating agreements with the major record labels to release custom music compilations under license with major brands, such as Ford Motor Company, Crayola, Care Bears and Elvis Presley Enterprises.

Harris also led Madacy’s strategy for the licensing of its entire music catalogue to Apple for their launch of the IPOD.

In 2011, Harris co-founded Starting Five Media, a company that specializes in recording and licensing custom renditions of popular songs as well as clearing the rights to the music composition for use by their clients in media projects.

Harris has negotiated publishing and master recording rights for many Top 40 songs for use in various media projects, TV Commercials and more.