The history behind Jada Pinkett Smith and Tupac Shakur's relationship

Jada Pinkett Smith and Tupac Shakur’s relationship has been making headlines for decades.

The topic of endless scrutiny, the pair met as teens in Baltimore before each went on to find respective fame. Shakur, as a musician, actor and rapper, and Pinkett Smith, an actor and wife of Hollywood superstar, Will Smith.

Though their friendship had its share of ups and downs, both professed a deep love for one another that lasted right up until Shakur was killed in 1996 during a drive-by shooting in Las Vegas.

While they weren't speaking at the time of his death, Pinkett Smith told Howard Stern in a 2015 interview that the rapper knew how much she loved him.

"I know he knew that," she said in the interview, "because it wasn’t the first time that we had had a bad argument and had stopped speaking and all that. I mean, that was kind of a constant in our relationship."

Shakur, too, often spoke of his affection for Pinkett Smith, even penning poetry in her honor, including the poem, "Jada," in which he wrote, "u r my heart in human form" and "u will never fully understand how deeply my heart feels 4 u."

In a 2022 appearance on Big Boy, Pinkett Smith's son, Jaden, said that at one point Shakur even proposed, saying "Tupac asked to marry my mom and she was like, 'Pac, we're best friends.'"

Pinkett Smith told Stern that their relationship was purely platonic, saying that there was "no physical chemistry between us at all," and the one time they attempted a kiss, it was "disgusting."

While their love may not have been romantic, it's one many people still talk about to this day. To better understand their long history, here's a timeline of Jada Pinkett Smith and Tupac Shakur's relationship.

1986: The beginning

Pinkett Smith and Shakur first met back in the '80s as sophomores at the Baltimore School for the Arts in Maryland. Their connection was instant and the teens became fast friends.

In a 2014 interview with Arsenio Hall, Pinkett Smith recalled, "'Pac was probably one of the first male figures that I had in my life that saw the beauty and the talent and my intelligence separated from sex," she said.

"It was about, ‘You, you’re a beautiful woman. You’re talented. You’re strong and I respect you and you are my girl. You gon’ sit right here and I'ma protect you. I’ma make sure, if nothing else, you get what you need.' That’s what our relationship was like. We kind of did that for each other.”

Of Shakur's appeal, Pinkett Smith told Howard Stern, “I had never in my life met a person like 'Pac. ... He had so much charisma."

According to Pinkett Smith, at the time of their meeting, she was selling drugs. “When we first met, I was a drug dealer,” she shared during a 2017 interview on Sway's Sirius XM radio show, adding that their roles would one-day reverse and that as she was “coming out of the life, he was going more into the life.”

Yet, their friendship was deep and binding and the pair spent much of their high school time together. In an oddly prophetic moment, they humorously lip-synced and recorded a version of “Parents Just Don’t Understand,” the ‘80s hit song by the Fresh Prince himself, Will Smith.

The '90s and the road to fame

Prior to his senior year at Baltimore's School for the Arts, Shakur left the East Coast for Marin City, California, where his charisma and writing skills soon paved the way to success.

In 1991, he released his debut album, "2Pacalypse Now" before being cast in the 1992 movie "Juice," a starring turn that led to other movie roles like "Poetic Justice" and "Above the Rim."

As his career was beginning to take off, so was Pinkett Smith's, who had dropped out of college to pursue a career in acting.

Scoring bit parts in in shows like "Doogie Howser, M.D." and "21 Jump Street," Pinkett Smith got her big break in 1991 when producer Debbie Allen cast her in the TV series "A Different World."

The two friends leaned on each other for support as their respective stars were rising, with Pinkett Smith securing Shakur a guest appearance on "A Different World." In turn, Shakur insisted she be cast in the Hughes Brothers film "Menace II Society," a movie he was originally slated to appear in before suffering a falling out with producers.

"We were always trying to look for opportunities to work together. It was because of 'Pac that I got 'Menace II Society,' and we were always looking out for each other like that. That's just how we did it," she said in an interview with Entertainment Weekly.

A bond that led Will Smith to suffer from 'raging jealousy'

After watching Pinkett Smith on "A Different World," Will Smith felt an instant chemistry with the actor. "I knew that there was something in our energy that would be magic," he recounted during a 2018 episode of "Red Table Talk."

Wanting to meet her, Smith says he arranged to attend a taping of the show. The person set to introduce the two actors was there with Sheree Zampino, the woman who'd go on to become Smith's first wife.

"I went to 'Different World' to meet Jada, and met Sheree, and ended up marrying Sheree and having Trey," Smith recalled on "Red Table." Eventually the couple divorced and, according to Smith, the minute it was final, he called Jada.

"I said, 'Are you seeing anybody?' And she said, 'No?' I said, 'Cool, you're seeing me now,'" Smith said.

The couple eventually married on New Year's Eve in 1997.

Pinkett Smith's close relationship with Shakur proved to be difficult for Smith, who wrote in his 2021 memoir, "Will," that when he and Jada were first together, his mind was "tortured" by her connection with the rapper.

"He triggered the perception of myself as a coward," Smith wrote. "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."

Smith continued, "When Jada and I committed to each other, and the demands of our relationship made her less available to 'Pac, my immature mind took it as a twisted kind of victory."

The "Independence Day" actor says in the book that he had been in the room with Shakur on multiple occasions, but never spoke to him because "the way Jada loved 'Pac rendered me incapable of being friends with him. I was too immature."

During an exclusive interview with TODAY, Pinkett Smith revealed that she and Smith have been separated since 2016.

1994: Shakur is sentenced to prison

Just as Pinkett Smith was leaving her drug-dealing days behind, Shakur was slipping into a dark world.

By 1994, the rapper had been arrested several times on weapons charges and convicted twice for assault. In November of that year, Shakur was robbed of $45,000 and shot multiple times during an attack in New York City, according to the Washington Post.

A few weeks later, while still recovering, Shakur was convinced of sexually abusing a fan and sentenced to prison starting in 1995.

"Jail was a very difficult experience for him," Pinkett Smith tells Stern during their 2015 interview.

After serving eight months of his four-year sentence, Shakur was released on bail and Pinkett Smith says that upon his release, the rapper had "changed quite a bit" while serving his time.

"We were on two sides of the spectrum," Pinkett Smith told Stern, saying that while they'd always had "intense conversations," upon Shakur's release from prison, they had a "very hardcore" falling out.

"I just wasn’t in agreement with the direction that he was taking," she explained. "And I just told him that it was a very destructive direction."

In return, Shakur accused Pinkett Smith of having "got Hollywood."

After the heated argument, the friends went their "separate ways," she said during the 2017 Sirius XM interview with Sway.

"I just felt like, 'OK, God, one day you're gonna do for 'Pac what you did for me, which is, you saved me.' And that just never happened for him," she said.

1996: Tupac Shakur is murdered in Las Vegas

On Sept. 7, 1996, Shakur attended a boxing match between Mike Tyson and Bruce Seldon at the MGM Grand Hotel in Las Vegas, according to the New York Times.

After the match ended, Shakur and an entourage that included Marion "Suge" Knight, co-founder of Shakur's label, Death Row Records, were driving to a nightclub when they pulled up to a stoplight.

While stopped, a white Cadillac pulled up alongside the BMW they were riding in, rolled down the window, and shot the rapper four times, leaving Shakur in critical condition.

Six days later, Shakur, 25, died in a Las Vegas hospital from his wounds.

"That was a huge loss in my life," Pinkett Smith said on "Red Table Talk."

"He was one of those people that I expected to be here and my upset is more anger because I feel that he left me. And I know that’s not true. And it's a very selfish way to think about it, but I really did believe that he was going to be here for the long run," she explained on the episode.

During a 2017 segment on TODAY, Pinkett Smith told Hoda Kotb and Kathie Lee Gifford that she sometimes struggles to come to terms with having survived her rocky past, while Shakur wasn't as fortunate.

"I often question, how can that be, how can that happen? How can two people, you know, have these parallel lives? One makes it and one doesn’t," she said. "And just realize, you know, even in his death, just feeling like he’s not getting his just. And I had to realize that’s, that’s not for me to decide, I have to let it go. I have to have peace with what 'Pac's fate is, what his destiny is and that it's not up to me to fix anything."

More than 25 years after Shakur was murdered in Las Vegas, Duane Keith Davis, a self-described gang member, was indicted in September of 2023 for killing the rapper in 1996, according to NBC News. To some, the arrest finally put closure on the long-unsolved crime.

“Now I hope we can get some answers and have some closure. R.I.P. Pac,” Pinkett Smith posted in an Instagram story after it was announced.

As for losing her best friend, "It definitely taught me a lesson," she told Howard Stern in 2015. "Which is life is too short. Do not let disagreements stand in between you and people that you love and care about."

This article was originally published on TODAY.com