Album: In My Lifetime, Vol. 1
Label: Roc-A-Fella/Def Jam
You can love or hate Jay-Z. Either or. You can roll with him or get rolled over. No exceptions.
On “Who You Wit,” Jay-Hov was hard on a chick and gave you nothing but that silver-tongue pimp talk. Thug bitches, shy bitches, and rough bitches? Yeah, Jay was an all inclusive mack.
Obviously, the player days are over for Young Hov, but his pimp hand was heavy in the late '90s. Even if Vol. 1 is often criticized for being too glossy, this record still worked. It's also worth noting that this line—“I sink this ball in your hole, I'm Tiger Woods"—would take on a whole new meaning a decade later. The man is a prophet!
55. Jay-Z "Who You Wit II" (1997)