Will Smith Regrets Jealousy Over Jada Pinkett Smith's Friendship With Tupac The actor revealed on ‘The Breakfast Club’ that he "couldn't handle" how close his wife was to Shakur. Pinkett Smith and Shakur met as teens and remained close until the rapper’s death. The ‘Bad Boys for Life’ star admitted his jealousy kept him from getting to know Shakur, despite Pinkett Smith's encouragement. Will Smith, via ‘The Breakfast Club’ Smith and Pinkett Smith met in 1994 on the set of ‘The Fresh Prince of Bel

Why Will Smith says he regrets never being Tupac’s friend

Will Smith may seem as if he’s the epitome of confidence, but the actor recently admitted wife Jada Pinkett Smith’s years-long friendship with Tupac Shakur made him jealous.

The “Bad Boys for Life” actor made the candid confession during a stop on “The Breakfast Club” radio show earlier this week.

» RELATED: Jada Pinkett Smith disputes accuracy of Tupac Shakur film

“That was in the early days,” said Smith, who was joined by his co-star Martin Lawrence. “That was a big regret for me, too, because I could never open up to interact with Pac.”

Pinkett Smith and Shakur attended Maryland’s Baltimore School of the Arts as teenagers. She explained in an episode of Facebook Watch’s “Red Table Talk” the pair had a “complex relationship” and that Pac would be protective over her as she dated.

She said that complexity emerged “in those moments of his, ‘Who’s that?!’” despite the fact that “there ain’t nothing like that between us.”  

Regardless of a lack of romance between the classmates, Smith explained that with Pinkett Smith and Shakur’s history, they’d “come into an age where now that was a possibility and then Jada was with me.”

» RELATED: Jada Pinkett Smith: There have been 'betrayals of the heart' during Will Smith romance

“So Pac had a little thing on that, but she just loved him like he was the image of perfection, but she was with the Fresh Prince,” he continued. “We were in the room together a couple of times and I couldn’t speak to him. You know, he wasn’t going to speak to me if I wasn’t going to speak to him.”

Smith admitted his wife told him he and Pac had lots in common, but the movie star couldn’t get past his jealousy to learn more about the rapper. 

He called it “a huge regret of mine.”

» RELATED: What was actor Will Smith doing in Pooler?

“I was deeply, deeply insecure, and I wasn’t man enough to handle that relationship,” Smith said.

Shakur was fatally shot in 1996, and Pinkett Smith has remarked on “Red Table Talk” about how much anger his death caused her to feel.

“(H)e was one of those people I expected to be here,” she said. “My upset is more anger because I feel like he left me. 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.”

Support real journalism. Support local journalism. Subscribe to The Atlanta Journal-Constitution today. See offers.

Your subscription to the Atlanta Journal-Constitution funds in-depth reporting and investigations that keep you informed. Thank you for supporting real journalism.

X