19. “Money Ain’t A Thing” Feat. Jermaine Dupri From Vol. 2… Hard Knock Life (1998)
Jay has recruited some of the greatest rappers ever in his catalog of collaborations: Eminem, Nas, Big Boi and Kanye to name a few. Jermaine Dupri will not make that list of greats. This was Dupri’s best-rapped song, which is kind of like saying you’ve seen Star Jones’ sexiest picture. It’s catchy despite Jermaine’s best efforts, but lackluster nonetheless.