Fat Joe Says Not Signing Eminem is His Biggest Regret

As Jay Z famously noted on his debut album Reasonable Doubt, "you gotta learn to live with regrets." But some can be harder to dismiss than others. Fat Joe recently talked about a rap game regret that will probably haunt him 'til his grave, revealing he had a chance to sign the biggest rapper in hip-hop history Eminem. Not only did he have one chance. He had multiple opportunities to recognize the then fledgling rapper's talents, but didn't take action. "Man I got so many regrets," the Terror Squad boss told the South China Morning Post in a recent interview. "The biggest is that Eminem gave me so many demos, six different times he approached me and I didn’t sign him. Shame on me."

Em, of course would go on to sign with Dr. Dre's Aftermath Entertainment in 1998 and turned out to be the biggest rap act, well, ever. And the rest they say is history.

While the Bronx rapper did let the big one get away, he should find solace in the fact the he did end up signing another rap legend, Christopher "Big Pun" Rios. Pun, signed with Terror Squad the same year Em linked up with Dre and put out his classic debut album Capital Punishment the same year. The album would cement the Puerto Rican MC as one of the most advanced lyricists in the game and would eventually go platinum, marking him as the first latino hip-hop artist to do so. Pun died in February 2000 after suffering a fatal heart attack.

Still, having Eminem on the roster would have been epic. Can you imagine dozens of Eminem and Big Pun collabs? (Head explodes)