Appearing on a recent edition of New York radio show The Breakfast Club, the rapper and actor was asked by host Charlamagne Tha God if he ever experienced feelings of jealousy due to the pair’s relationship.
“Fuck yeah,” he responded.
“That was in the early days,” he explained. “That was a big regret for me, too. Because I could never open up to interact with ‘Pac.”
Smith went on to say that 2Pac (real name Tupac Shakur) and his wife “never had a sexual relationship, but now they had come into that age where that was a possibility, and Jada was with me.”
The star added that Jada “just loved” the later rapper, saying: “He was the image of perfection, but she was with the Fresh Prince so it was, like, we were in the room together a couple [of] times, I couldn’t speak to him.
“[Shakur] wasn’t going to speak to me if I wasn’t going to speak to him.”
Smith revealed that despite Jada’s efforts, he and Shakur never struck up a bond. “That was a huge regret of mine,” he admitted.
Jada and Shakur attended Baltimore School of the Arts together before each becoming famous.
Back in November, Jada described her relationship with the ‘California Love’ artist as “complex” during an appearance on Red Table Talk.
“Him feeling like, ‘You’re the only stability I got, I can’t afford for you to put that attention elsewhere’,” Smith told host Robyn Crawford. “For him, it was, we were an anchor for each other. Anytime he felt like that anchor was threatened, oh my God.”
Will Smith, meanwhile, has impressed fans by rapping his entire career history in just 150 seconds during an episode of The Tonight Show Starring Jimmy Fallon.