Despite being one of the biggest stars of the 90s, Will Smith still found himself getting jealous of Jada Pinkett Smith’s close relationship with 2Pac.

Jada and the late, great rapper were famously close friends, attending the Baltimore School for the Arts together. In his new memoir, simply called Will, Smith reveals that he was very insecure about their relationship back then, as per Complex.

“Though they were never intimate, their love for each other is legendary – they defined ‘ride or die,’” Smith says in his memoir. “In the beginning of our relationship, my mind was tortured by their connection. He was PAC! and I was me. He triggered the perception of myself as a coward. I hated that I wasn’t what he was in the world, and I suffered a raging jealousy: I wanted Jada to look at me like that.”

The Fresh Prince of Bel-Air icon also admitted that he was “too immature” to be able to be friends with the rapper. “If she chose me over Tupac, there was no way I could be a coward,” he writes. “I have rarely felt more validated… I was in a room with Tupac on multiple occasions, but I never spoke to him. The way Jada loved Pac rendered me incapable of being friends with him. I was too immature.”

The actor has been open previously about his struggles with his now-wife’s bond with 2Pac. When he was asked on The Breakfast Club last year if he ever felt “jealous” of their closeness, he was forthright with his answer. “Oh, fuck yeah. Oh my god, that dude. And you know that was in the early days, too. That was a big regret for me because I could never open up to interact with Pac.”

He continued: “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. But then come into that age where now that was a possibility, and Jada was with me, so Pac had a little thing on that. But she just loved him, he was the image of perfection but she was with the Fresh Prince.”

For more on this topic, follow the Film & TV Observer or the Hip Hop Observer.

Check out Will Smith discussing Jada and 2Pac’s relationship on The Breakfast Club: