As unsigned Eminem lived in New Jersey in the late 1990s. Running with Pacewon and The Outsidaz, doing 12″ singles on small New York City independent labels, the Detroit, Michigan MC made a lot of impact trying to earn a lasting spot in the Hip-Hop/music industry. As fate would have it, it would be the Los Angeles, California-based Dr. Dre who would help make those dreams become every bit of a reality.

However, during that time, Marshall Mathers knocked on other doors. The twenty-something wise-cracking MC famously toyed with running with Buckshot, Dru Ha, and Duck Down Records. The D12/Bad Meets Evil member was also very close to the Rawkus Records nucleus, including Talib Kweli, El-P, and The High & Mighty. However, did you know that Em’ also stepped to Fat Joe looking for that deal?

Speaking with The South China Morning Post last week, Joey Crack recalled the skinny rapper stepping to him on half a dozen occasions. “I got so many regrets,” said the member of Terror Squad and Diggin’ In The Crates (D.I.T.C.). “The biggest [regret] is that Eminem gave me so many demos – six different times he approached me and I didn’t sign him. Shame on me.”

Joe has succeeded in discovering talent though. The Bronx, New York MC (discovered by Diamond D in his own right) is largely responsible for the mainstream breakthrough of Big Pun, Remy Ma, as well as early production work for DJ Khaled.

In 2005, on Joe’s All Or Nothing album, he and Eminem worked together on the “Lean Back remix.” But, die-hard Heads know that Em’ and Joe freestyled in those wild late 1990s, alongside another BX MC, the “rhyme inspector” Percee P:

In the mid-2000s, Fat Joe would be at odds with Eminem’s own star signing: 50 Cent.

Read more about Fat Joe’s recent trip to Hong Kong, his reflection on his career, and upcoming plans in the The South China Morning Post.

How do you think Fat Joe and Eminem’s careers would be different had Joe liked those demo tapes? How would Eminem have sounded alongside Big Pun, Armageddon, Triple Seis, Prospect, and Cuban Link on 1999’s The Album (boasting beats by Alchemist, Buckwild, Juju and more)?

Related: Did You Know Eminem Was Originally Going to Sign with Buckshot and Duck Down? (Video)