Jay-Z f/ Blackstreet "The City Is Mine" (1997)

When platinum plaques eluded Jay-Z's Reasonable Doubt, he sought them out with the more radio-friendly follow-up In My Lifetime, Vol. 1. He scored a minor hit with "The City Is Mine," which paired Jay's trademark lyrical finesse with guest vocals from Teddy Riley's R&B group Blackstreet. Jay was in rare form, but Blackstreet's rehash of the old Glenn Frey hit "You Belong to the City" felt out of place and reeked of desperation for a bankable hit. Also, we're still waiting for someone to explain to us what being "A man of the night" entials and how it applies to Jigga.