When OutKast dropped “Ms. Jackson” in the fall of 2000, the world was stunned. Nobody had ever heard a hip-hop song that sounded anything like this. But there’s never been anybody like OutKast before. The Atlanta duo, made up of Andre 3000 and Big Boi, brought their innovative hip-hop style to the pop charts with “Ms. Jackson,” from their album Stankonia. “Ms. Jackson” blew up into their first Number One hit, and it’s gone down in history as one of the group’s definitive classics. It comes in at Number 145 on Rolling Stone’s list of the 500 Greatest Songs of All Time.
Stankonia was OutKast’s fourth album, but the first one since their big commercial breakthrough with the 1998 blockbuster Aquemini, which made them superstars. Expectations were high. The first single from “Stankonia” was “B.O.B. (Bombs Over Baghdad),” a radically inventive Afro-futuristic behemoth that proved too much for radio to take. “B.O.B.” exploded out of the speakers with elements of gospel, rock, and drum-and-bass beats. For many fans, it still remains the peak of their jam-packed catalog. But it was too revolutionary to make it on the radio. “Ms. Jackson” sounded nothing like “B.O.B.,” yet the two songs had that same innovative spirit, breaking down different kinds of barriers. This time, the radio couldn’t resist. Nobody could.
“Ms. Jackson” sounded daringly confessional, with Andre 3000 sending a song out “to all the babymamas’ mamas’ mamas.” He addressed his real-life broken romance with Erykah Badu, and his strained relationship with her mother. “I’m sorry, Ms. Jackson, I am for real,” he sings to his ex’s mama. “Never meant to make your daughter cry / I apologize a trillion times.”
Andre was going for deep soul, writing the song on acoustic guitar before bringing in the beats. “Ms. Jackson” was so vulnerable and open, it made everything else on the radio sound a little half-hearted. He pledges to be there for their son as a father, but also mourns the evanscence of love, asking, “Forever? For-ever-ever? For-EVER-ever?” Big Boi comes in with a very different perspective on breaking up and moving on. The groove comes from a Seventies funk classic, “Strawberry Letter 23” by the Brothers Johnson. It sums up the independent spirit that Andre and Big Boi have always shared, whether together or alone, right up to Andre’s flute music and Big Boi’s owls.
“Ms. Jackson” became a universal smash, hitting Number One in February 2001. Everybody loved this song — even the real-life inspiration. “How did my mama feel?” Badu said on the Rap Radar podcast. “Baby, she bought herself a ‘Ms. Jackson’ license plate. She had the mug, she had the ink pen, she had the headband, everything. That’s who loved it.”
On this week’s episode of Rolling Stone’s 500 Greatest Songs, hosts Rob Sheffield and Brittany Spanos discuss “Ms. Jackson,” and how it fits into the long illustrious OutKast story. They’re joined by their brilliant Rolling Stone colleague Simon Vozick-Levinson as they break down this song, its timeless appeal and the mighty legacy of OutKast.
In 2004, Rolling Stone launched its 500 Greatest Songs of All Time list. Tabulated from a massive vote that had artists, industry figures, and critics weighing in, the list has been a source of conversation, inspiration, and controversy for two decades. It’s one of the most popular, influential, and argued-over features the magazine has ever done.
So we set out to make it even bigger, better, and fresher. In 2021, we completely overhauled our 500 Songs list, with a whole new batch of voters from all over the music map. Rolling Stone’s 500 Greatest Songs takes a closer look at the entries on our list. Made in partnership with iHeart, Rolling Stone’s 500 Greatest Songs finds Brittany and Rob discussing a new song each week, delving into its history and impact with the help of a special guest — including fellow RS colleagues, producers, and the artists themselves. It’s our celebration of the greatest songs ever made — and a breakdown of what makes them so great.
Check out the latest episode above, on iHeart, or wherever you get your podcasts, and look for new episodes every Wednesday.
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