Long before Jada Pinkett Smith met Will Smith, she shared a rather close bond with Tupac Shakur. When the Smiths met on the sets of The Fresh Prince of Bel-Air, neither had any idea as to how their lives would soon be entwined for decades to come. Now married for 26 years, the couple’s relationship has seen its fair share of ups and downs. Earlier in their relationship, some of the rifts that formed even surrounded the now-deceased 2Pac.

This is because the Emancipation actor was battling some shocking insecurities that he later ended up regretting.

Smith on his relationship with Tupac Shakur

In 2020, while interacting with The Breakfast Club, Will Smith revealed how “deeply insecure” his wife’s relationship with 2Pac made him feel. Not only did he feel “jealous” of their bond, but also failed to “interact with Pac” because of it, which became a “big regret” of his. Even when both rappers were in the same room, they would refuse to initiate a conversation. Regardless of his wife insisting that they were both pretty “similar“.

While Smith admitted to being insecure, his wife Jada Pinkett Smith does not harbour the same feelings. A few years back, she revealed how she did not find her husband being attracted to other women problematic. Yet, the King Richard said that back then he did not feel “man enough” to accept their relationship. Which was a shame considering the musical masterpiece that could have resulted from a jamming session between them.

All this begs the question as to why Will Smith felt insecure about 2Pac in the first place.

Why did Jada Pinkett Smith and 2Pac’s love scare Will Smith?

As per the I Am Legend actor, he was just a “soft rapper from Philly” back then, whereas Shakur was a legend and also the “image of perfection” in his wife’s eyes. However, it was not only Shakur’s relationship with his wife that made him “jealous.” In Smith’s memoir which came out in 2021, he also delved into why the ‘Dear Mama’ rapper’s passion and fearlessness made him envious. 

According to him, the way Shakur was able to stand up to his abusive father was something that made him feel inadequate in himself. Often, the Smith family household’s dirty laundry is aired out in public. However, it is the same trait that makes the celebrity family so endearing to fans. 

What do you think of the Bad Boys actor’s regrets over the past with Tupac Shakur? Share your thoughts in the comments.