This week, Will Smith and Martin Lawrence’s Bad Boys For Life hits theaters for a January 17 premiere. The longtime friends and fellow actors sat down with the Breakfast Club to discuss the new film, including the franchise’s beginnings, personal growing pains, and their impact on Black culture. At one point in the discussion, Charlamagne Tha God brings up the friendship between Will Smith’s wife, Jada Pinkett Smith, and Hip-Hop superstar, Tupac Shakur.

“We’ve been wildly tested. We have tested each other,” Will Smith says earlier about his relationship with his wife. The couple began dating in the mid-1990s, after a guest appearance on The Fresh Prince Of Bel-Air. They married on the last day of 1997. “We have tested our commitment to the partnership. We have tested our commitment to our family. There is a certain amount of, let’s say, battery that you have to subject each other to in order to know that you are really down.” Then, Smith jokes, “And it ain’t nothin’ I’m talking about on The Breakfast Club.”

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Despite Will Smith’s joshing declaration, Breakfast Club host Charlamagne Tha God presses further, asking Will if he was ever jealous of Jada’s love for Tupac Shakur. “Oh, f*ck yeah. Oh, my God. Dude. That was in the early days,” he notes. In 1994, Tupac was also in Hollywood. “That was a big regret for me, too, because I could never open up to interact with Pac because we had a little bit of a thing, right? [Jada and him] grew up together, and they loved each other, but they never had that. They never had a sexual relationship. But they had come into that age where that was a possibility, and then Jada was with me. 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. I just never could, even we were in the room together a couple of times. I couldn’t speak to him. He wasn’t going to speak to me if I wasn’t going to speak to him.”

Jealousy and unresolved feelings about a partner’s past relationships can create emotional barriers that are difficult to navigate, even in otherwise strong relationships. Will’s openness about his feelings toward Tupac reflects a common challenge couples face—how to handle feelings of inadequacy or comparison. Emotional insecurity often stems from unresolved fears of not being enough or of losing connection, which can silently chip away at a relationship over time. This is where couples therapy can play a transformative role.

In therapy, partners have the opportunity to explore these underlying emotions in a supportive environment, learning how to communicate openly and without judgment. Understanding that a partner’s past does not diminish their present commitment is key to building trust and emotional security. Couples therapy helps individuals recognize and validate their feelings while guiding them toward healthier patterns of communication and emotional intimacy. Addressing these issues head-on allows couples to move beyond jealousy and comparison, strengthening their bond and fostering a deeper sense of mutual respect and understanding.

Jada Pinkett, a native of Baltimore, Maryland, met Tupac during his time there. He wrote love poems for the would-be actress, published after Tupac’s September 1996 murder.

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During the interview, near the 31:00 mark, Charlamagne explains that he thinks Tupac and Will would have had a lot in common. Smith continues, “That’s what Jada would say all the time. She was like, ‘I’m telling you, y’all are so similar. You’ll love him.’ And I just never, you know, that was a huge regret of mine. I couldn’t handle it. I was [perceived as] the soft rapper from Philly, and he was Pac. I was deeply, deeply insecure, and I just wasn’t man enough to handle that relationship.”

There is also old video footage of Jada Pinkett interacting with another late Rap star, Eazy-E.

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Elsewhere in the interview, Will Smith and Martin Lawrence confirm that Bad Boys was initially planned to star SNL cast alums Dana Carvey and Jon Lovitz. Smith remembers giving Queen Latifah, who co-starred with Pinkett in Set It Off, her first acting role. Martin Lawrence also discusses his stand-up career.