4. "99 Problems" (2004)
Jay-Z paid Rick Rubin a visit to "recapture that feeling I had when I was a kid," as he explained in documentary Fade to Black. What came out of that session did have vintage heavy metal riffery reminiscent of Rubin's Eighties work with LL Cool J and Beastie Boys, but lyrically it was a blistering, modern-day critique, taking aim at those who demonize him as a black man and rapper. The hook, borrowed from Ice-T and Brother Marquis of 2 Live Crew – "I got 99 problems but a bitch ain't one" – was bait for talking heads, since verses play with the other meanings of the word. "[E]ven as I was recording it, I knew someone, somewhere would say 'Aha, there he goes talking about them hoes and bitches again!'" Jay writes in Decoded. The song became iconic enough that Barack Obama brought it to the 2013 White House Correspondents Dinner: In light of Jay and Bey's controversial visit to Cuba, he said, "I've got 99 problems and now Jay-Z is one," to hearty laughs.