The Jay-Z/Sinatra link isn’t so far-fetched. Both grew up on the poor fringes of New York — Sinatra in Hoboken, Jay-Z in the Marcy projects in Brooklyn — and made A-number-one through mastery of craft, business smarts and exploitation of their own hyper-masculine poise. Theirs is the story of the bad boy made very, very good, who breezes stylishly through high society with an impossibly glamorous woman on his arm, yet never loses his street-smart edge.
Jay-Z Boasts He’s the New Sinatra - NYTimes.com