Written by Lauryn Hill, this was the singer's debut single. The song is a warning against guys who are more interested in frivolous, expensive things than their girlfriends or families. Hill had some difficult relationships that may have inspired this; she dated Wyclef Jean from her group Fugees and was once engaged to Rohan Marley, son of Bob Marley.
This won the 1998 Grammy Award for Best Female Rhythm & Blues Vocal Performance. Hill also won for for Best Rhythm & Blues Song. The album received 11 nominations, making it the first hip-hop record to receive that many. It won five, making Hill the first female artist to win that many.
The album was named after The Mis-Education Of The Negro, a book by Professor Carter G. Woodson, an American black history expert, and The Education of Sonny Carson, an autobiographical film about the title controversial activist. The album, which was written, arranged and produced entirely by Hill, was about the education one receives after leaving school, the life learning process.
With this song, Hill became the first woman since Debbie Gibson to debut at #1 on the Billboard Hot 100 with a song she wrote, recorded, and produced on her own. Gibson did the same with "Foolish Beat
" in 1989.
It was an accomplishment Hill was not encouraged to make. "For some reason, women aren't taken seriously as thinkers and creators and arrangers and producers," she told Playboy
. "The industry thinks there always has to be some man somewhere puppeteering the whole situation. It doesn't make you feel good as an artist when you are having conversations about your music and people don't take it seriously."
Hill wanted to prove that a female artist could use her brains to have a chart-topper rather than her body, unlike fellow performers like Lil' Kim. She told Details magazine: "I'm not dissing them, I'm dissing their mind-set. My music talks about a certain way of thinking, and if the cap fits, you know? I knew girls like Kim growing up - I might have even been one at certain age - and there's a huge lack of self-esteem behind that thinking. I mean, when I was 14 I thought that if a guy didn't whistle at me, that meant I wasn't pretty. But either you mature past that or you get caught in the concept of, 'Oh, I have to show some ass, 'cause that's the only way I can feel beautiful.' Sex is cool, but it's only part of the story."
The music video, shot in Manhattan's Washington Heights, uses a split-screen to show two different Hills performing the song. On the left, she's decked out like a '60s-style R&B star, while on the right she's a modern hip-hop performer.
This was used on the MTV animated series Daria in the 1999 episode "Through a Lens Darkly."
Glee's Amber Riley and Naya Rivera covered this on the 2014 episode "Back-Up Plan."