Outkast - "Ms. Jackson"
Reached No. 1: February 17, 2001 Weeks at No. 1: One
Although it's an obvious classic now, "Ms. Jackson” is arguably the track that propelled the underground kings of Atlanta onto the global stage. The second single off of the masterful Stankonia, "Ms. Jackson" won a Grammy in 2002 for Best Group Rap Performance and it’s been in rotation ever since; people pride themselves on knowing every single word to this song. Apparently “Ms. Jackson” was originally written as an acoustic track—which thank Basedgod didn't stick, because that guy at the party with a guitar would have played it four times by now.
What’s best about “Ms. Jackson” is it’s sweet earnestness. The song is about the pair's relationships with mothers; their own mothers and the mothers of their children, and Big Boi and André say some pretty deep things about the transience of relationships that are worth listening to twice.