Jay got famous first and foremost for rapping well on hit songs. He's definitely mostly famous for being famous now, but 99-03? Nah dogg. The music brought him to the party - dumb "mogul" myth making and marrying Beyonce kept him there.
Drake is cool. In fact I loved "Take Care" and last year's "If You're Reading This" was my favorite album of 2015...and he's definitely as big now as Jay was in 2000 I'll give you that. But Drake is probably the most deliberate rap star we've ever seen. I mean who knows if he even writes his own songs, right? That's evidence of someone who's obsessed with perception. He wants to be everything to everybody, and that's ok too because he's actually pretty good at everything (great on SNL last night) But all Jay wanted to be from 99-03 was the most badass rapper in the world - and he was.
Drake is good but he doesn't have a Can I Live. Period. No Dynasty Intro, no Heart of the City, no So Ghetto. Drake's Tuscan Leather is awesome; U Don't Know is an earthquake. Even Drake's smashes don't compare to Hov's honestly - Drake would sell a testicle for an anthem as unanimously approved of as Big Pimpin.