24. "Imaginary Player" (1997)
Bad Boy in-house producer Daven "Prestige" Vanderpool inverts "Imaginary Playmates," R&B duo Rene and Angela's 1981 hit about fantasy lovers, into this track comparing Jay's stacks to jealous rappers with "little to no dough/Sell a bunch of records and you still owe dough." All of Jay's trademarks at the time – the humor, the braggadocio, the quiet cockiness – are embodied on In My Lifetime, Vol. 1's slickest track. "Y'all want to take my flow, and run with it," he rhymes. "That's cool, I was the first one with it." "The original 'Imaginary Playmates' tag/hook and beat fit perfectly into their version beat-wise," Rene and Angela's Angela Winbush tells Rolling Stone. "A 13-year-old once asked me why was I singing ["Imaginary Player"] in my show and wrote so many lyrics to Jay-Z's song! I just laughed and said go ask your mother or grandmomma." Ma$e claimed to be the target of Jay's vicious broadsides, but whoever it's about, this is Exhibit A whenever you hear Jay's flow described as "effortless."