Hindsight is always 20/20. This is especially true for Will Smith, who recently admitted to feeling jealous of his wife Jada Pinkett Smith’s friendship with the late rap icon Tupac Shakur.

Smith stopped by Power 105’s The Breakfast Club with co-star Martin Lawrence to promote the highly-anticipated Bad Boys for Life film. When asked if he recalls ever being “jealous” of Pinkett Smith’s friendship with the rapper, he responds, “f—k yeah.”

“That was in the early days,” Smith said. “That was a big regret for me, too, because I could never open up to interact with Pac.”

Pinkett Smith and Shakur met in the mid-1980s at the Baltimore School for the Arts in Maryland. They both rose to fame in the early ’90s as she landed a role in A Different World, and his music with the rap group Digital Underground took off. Though their relationship was completely platonic, Smith said he was never fully comfortable with it.

“They never had a sexual relationship, but now they had come into that age where that was a possibility, and Jada was with me,” Smith explained.  “So Pac had a little thing on that, but she just loved him. He was the image of perfection, but she was with the Fresh Prince.” 

Tupac Shakur (Photo by Kevin Mazur Archive/WireImage)

Smith was man enough to admit that his insecurity about his wife’s friendship with Shakur prevented him from forging a genuine bond with the rapper. “It was like I never could even, we were in the room together a couple of times and I couldn’t speak to him,” he explained. “You know, he wasn’t going to speak to me if I wasn’t going to speak to him.”

Host Charlamagne chimed in that he thought Smith and Shakur would be kindred spirits. Will agreed. “Yeah that’s what Jada would say all the time,” he revealed. “Like, ‘I’m telling you, y’all are so similar you will love him,’ and I just never…That was a huge regret of mine. I couldn’t handle it. I was the soft rapper from Philly and he was Pac. You know what I mean? I was deeply, deeply insecure, and I wasn’t man enough to handle that relationship.” 

Tupac Shakur was notoriously killed in a drive-by shooting in 1996. During an episode of Red Table Talk, Pinkett Smith tearfully opened up about how his untimely death still affects her to this day.

“He was one of those people I expected to be here,” she admitted. “My upset is more anger because I feel like he left me. And I know that’s not true and it’s a very selfish way to think about it… I really did believe he’d be here for the long run. And when I think about it I still get really mad.”

Watch the full Breakfast Club interview below.

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