Will Smith Admits His Jealousy Of Tupac and Wife Jada Pinkett Smith’s Relationship, Now The Actor Regrets Never Interacting With Late Rapper

Actor Will Smith is one of the most recognizable film stars in the world but it’s his musician days that still haunt him. The Grammy award winning “Parent’s Just Don’t Understand” rapper thought that his “soft” persona was not enough of a match for Jada’s best friend rapper Tupac Shakur and now he’s sharing his regret of not being able to connect with the slain rapper for the sake of his wife.

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A post shared by Tupac❤️Jada (@tupac.jada) on Dec 22, 2015 at 8:42pm PST

There’s been a lot of renewed chatter about the Smith’s relationships with each other, due to the allegations being levied by R&B singer August Alsina. While neither Will Smith nor Jada Pinkett Smith have directly debunked these rumors, both have issued statements apparently via their representatives.

Jada Pinkett Smith’s youngest, Willow Smith, is also a co-host on her mother’s talk show Red Table Talk, so one can imagine the awkward discussion that might be happening soon on the family show. In a previous discussion on the show with August Alsina, Willow was in fact not at the Red Table Talk table. The other co-host, Willow’s grandmother Adrienne Banfield-Norris was, while Jada drove the interview about Alsina’s struggles with drugs.

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A post shared by ∴ WILLOW ∴ (@willowsmith) on Nov 21, 2019 at 12:24pm PST

Willow’s been affected by one of her mother’s relationships before, however. It’s a well-known fact that Jada Pinkett Smith was great friends with rapper Tupac Shakur, and also that his passing affected her greatly. The two were so close that many assumed they were more than just friends, but Jada’s denied multiple times — because she’s been married to Will since 1997.

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A post shared by Tupac❤️Jada (@tupac.jada) on Dec 22, 2015 at 11:47am PST

Jada previously said that the pair attempted kissing once, but confessed that they lacked the “physical chemistry” necessary when it comes down to romance. It’s resurfaced now that young Willow Smith also was a fan of her mother’s friend Tupac and that she wanted him to “come back” after his death to make her mother “happy.”

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A post shared by ∴ WILLOW ∴ (@willowsmith) on Jun 21, 2020 at 12:02pm PDT

Back in 2012, Willow posted a shot of a letter that she wrote to Tupac on her Instagram. In the now deleted post, Willow wrote, “Dear Tupac, I know you are alive someplace. I think that my mommy misses you. Can you come back so mommy and me can be happy! I wish you were here… I really do! Love, Willow.”

Apparently young Willow Smith was only 11 years old when she wrote the letter, and it seems to show that Tupac’s death did have a profound affect upon herself and her mother Jada.

When asked previously by The Breakfast Club’s Charlamagne Tha God if he ever felt “jealous” of the “California Love” rapper, Will replied: “F–k yeah, and that was in the early days.” He continued honestly: “That was a big regret for me too because I could never open up to interact with ‘Pac. We had a little bit of a thing because they grew up together and they loved each other but they never had a sexual relationship.”

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A post shared by Tupac❤️Jada (@tupac.jada) on Dec 22, 2015 at 11:22am PST

Revealing the extent of the tension between them, Will recalled: “We were in the room together a couple of times and I couldn’t speak to him. He wasn’t going to speak to me if I wasn’t going to speak to him.” Though Pac himself was more of a “hardcore” rapper at the time, Will knew that he wasn’t a total slouch himself.

“‘Pac had a little thing on that, but she just loved him,” he admits. “He was the image of perfection, but she was with the Fresh Prince.” In the end, Will confessed to the fact that he was the immature one between the two and he had regrets about his actions.

“That was a huge regret of mine and I couldn’t handle it. I was the soft rapper from Philly and he was ‘Pac. I was deeply insecure and wasn’t man enough to handle that relationship.”

See the interview below.