Nelly — "Ride wit Me"

"If you wanna go and take a ride wit me..." — HEY, MUST BE THE MONEY! Nelly's acoustic-guitar bounce was the sound of every radio, mall, and school bus in 2001, the laid-back victory lap off Country Grammar.

Released on February 13, 2001, as the third single from Country Grammar, "Ride wit Me" was Nelly's biggest hit yet — number three on the Billboard Hot 100 (and number three in the UK), five-times platinum, with a video that won Best Rap Video at the 2001 MTV VMAs. Where "Country Grammar" bounced, this one glided: an easy acoustic-guitar groove under a hook built for shouting the answer back — "hey, must be the money!", a phrase Deion Sanders had popularized (he recorded a song by that name in 1994). The "brush your hair" section earned DeBarge songwriting credits for interpolating their 1982 hit "I Like It."

The song carries a story most people singing along never knew. The featured third verse belongs to City Spud — Lavell Webb, Nelly's half-brother and fellow St. Lunatic — who was already in a Missouri prison before Country Grammar even came out, serving a ten-year sentence for a 1999 robbery. He couldn't appear in the video (the other Lunatics lip-sync his lines), and by Nelly's own telling, the Band-Aid he famously wore on his cheek — first covering a real basketball scar — was kept on as a tribute to him until his release in 2008. So the breeziest radio song of 2001 doubled as a top-three hit for a man listening from a cell, and the St. Lunatics titled their 2001 group album Free City in his honor.

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