Will Smith Admits He Was Jealous of Jada Pinkett Smith’s Relationship With Tupac Shakur — ‘Oh, F*ck Yeah’

Will Smith and Jada Pinkett Smith were thrust back into the public eye this summer because of Jada’s entanglement with August Alsina. However, the couple proved their relationship is rock solid when discussing the transgression on Jada’s Red Table Talk. Will also admitted this year that he was jealous of his wife’s relationship with the late rapper Tupac Shakur. 

Jada Pinkett Smith and Will Smith
Jada Pinkett Smith and Will Smith | Ron Wolfson/WireImage

Jada Pinkett Smith met Tupac Shakur on her first day of high school

The young teenagers, Jada and Tupac, met at the Baltimore School for the Arts, and they immediately became friends. 

“But as soon as he approached me, he was like a magnet,” Jada once told Howard Stern. “Once you paid attention to him, he kind of sucked you in. And we hit it off from that moment on… I don’t think either one of us thought we would have made it in the way that we did, but we knew we were gonna do something.”

The two were very close, but there was no physical connection between them. 

Jada Pinkett Smith and Tupac Shakur
Jada Pinkett Smith and Tupac Shakur | Kevin Mazur Archive/WireImage

“There was a time when I was like, ‘Just kiss me! Let’s just see how this goes,'” Jada told Stern. “And when I tell you, it had to be the most disgusting kiss for us both.” 

Jada revealed that she was getting out of a life surrounded by crime, while Shakur was getting into it. She was devastated when the rapper was killed in 1996.

Will Smith revealed that he was jealous of Jada’s relationship with Shakur

When Will was promoting his film Bad Boys for Life with Martin Lawrence, he opened up about jealousy during an interview with The Breakfast Club radio. Will was asked if he was “ever jealous of the love Jada had for Tupac?”

“Oh, f**k yeah,” the actor responded. “That was in the early days. That was a big regret for me, too, because I could never open up to interact with Pac.”

Tupack Shakur in 'Gridlock'd'
Tupac Shakur in a scene from the film ‘Gridlock’d’ | Gramercy Pictures/Getty Images

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Will revealed that he couldn’t bring himself to speak to Shakur, despite being in the same room with the late rapper numerous times. 

“They had come into the age where now that was a possibility, and Jada was with me,” Will recalls about the Jada and Shakur finally being old enough to have a physical relationship. “Pac had a little thing with that, but she just loved him. He was the image of perfection, but she was with the Fresh Prince.”

Jada thought Will and Shakur had so much in common

Will seldom used profanity in his music, while Shakur used plenty of swear words. The two rappers seemed like opposites. However, both Jada and co-host of the radio show, Charlamagne the God, believed the two have more in common than they thought. 

Actors Trey Smith and Jaden Smith and Jada Pinkett Smith,  singer Willow Smith and actor Will Smith
Actors Trey Smith and Jaden Smith and Jada Pinkett Smith, singer Willow Smith and actor Will Smith | Randy Shropshire/Getty Images for Environmental Media Association

“That’s what Jada would say all the time,” Will responded. ‘I’m telling you, y’all are so similar, you would 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.”

If Shakur was alive today, maybe he and Will would be friends after all.