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One was an iconic rapper and poet tragically gunned down and killed in a drive-by hit. The other, a self-confessed “soft rapper from Philly.” But Jada Pinkett Smith loved them both. In a recent interview on radio show The Breakfast Club, Will Smith shocked everyone with his honesty when discussing how he felt about his wife’s special bond with Tupac Shakur.

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On the face of it, the relationship between Shakur and Pinkett Smith seems a surprising one. Shakur was born in East Harlem, New York in 1971, but 13 years later his family moved to Baltimore. It was there that he attended the Baltimore School for the Arts. On his first day there he met the future Mrs Will Smith, Jada Pinkett.

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Pinkett herself was a Baltimore native who had also been born in 1971. She studied dance and theater at the school and was to become exceptionally close to her classmate Shakur. He, for his part, studied poetry, acting, jazz and ballet at the institution. Before he moved to California in 1988, the two cemented what was to be a longstanding connection.

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Even after the rapper had set up home a short distance from San Francisco, Pinkett and Shakur remained in each other’s hearts. He wrote a poem entitled “Jada” in his collection The Rose That Grew From Concrete. In fact, although Pinkett’s life was to take a different direction after high school, she has spoken about how they were kindred spirits as classmates.

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Pinkett, of course, went on to meet and marry rapper and actor Will Smith. A few years older than Pinkett and Shakur, Willard Carroll Smith Jr. had entered the world on September 25, 1968, in Philadelphia, Pennsylvania. Although a promising student, his heart lay elsewhere – in his unique brand of catchy rap. With friend Jeffrey Townes, he formed hip hop duo DJ Jazzy Jeff & The Fresh Prince in 1985.

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Townes was DJ Jazzy Jeff, then, and Smith, The Fresh Prince. Their first single, “Girls Ain’t Nothing But Trouble,” was a hit in 1986, before Smith had even left school. They made an album, Rock The House, before winning a Grammy in 1989 for their performance of toe-tapping track “Parents Just Don’t Understand.”

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But it was to be their follow-up single, “Summertime,” that snared them a second Grammy and international recognition. Yet despite their successes, by 1989, Smith had mismanaged his money and found himself with a huge $2.8 million tax bill. Although he paid off what he owed, a huge acting opportunity in 1990 couldn’t have come at a better time.

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Smith was offered the titular role in what was to become a TV phenomenon, The Fresh Prince of Bel-Air: indeed, the whole sitcom was written around him. In the show, he starred as a kid from the wrong side of the tracks who moves in with his well-off relatives. It ultimately ran for six series from 1990 to 1996 and was an outstanding success.

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It is safe to say that it made Smith a star and his character, The Fresh Prince, a household name. In fact, the sitcom turned out to be one of the most iconic shows of the 1990s. Even today, The Fresh Prince’s street-smart adventures live on in a thousand gifs. Nearly 25 years after the final series, it is rerun worldwide and there are talks of a possible reboot.

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On the back of the show’s success, Smith was offered several major acting roles. His self-declared mission was to become the “biggest movie star in the world,” and by the mid-’90s he was well on his way to achieving his aim. After starring in Six Degrees of Separation in 1993, he hit box-office gold with Bad Boys two years later.

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The latter film, in which he starred opposite Martin Lawrence, grossed over $141 million in cinemas, and later spawned a 2003 sequel, Bad Boys II. A leading role in blockbuster Independence Day, at the time the second-most-successful film of all time, followed in 1996. Smith was turning out to be one of the most bankable stars in the business.

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Then, the following year, the singer-turned-actor hit cinema screens as Agent J opposite Tommy Lee Jones in Men In Black. The film was a triumph in its own right, earning almost $600 million at the box office worldwide. By performing the title song of the movie’s soundtrack, Smith was also to launch his hugely successful solo singing career.

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The single “Men In Black” topped the charts in the U.S. and U.K. in the summer of 1997, along with several other countries worldwide. The album of the same name saw further successful solo hits for Smith, including “Just Cruisin’” and “Gettin’ Jiggy Wit’ It.” The world couldn’t seem to get enough of his brand of family-friendly, infectious rap.

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But behind the scenes, Smith’s love life was proving a little more complicated. He had married Sheree Zampino in 1992, and a son Trey was born in November of the same year. However, the relationship didn’t last and the movie star and Zampino divorced three years later. Smith’s song “Just the Two of Us” in 1998 was based on his experience of bringing up his son despite being separated from his mom.

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Meanwhile, Smith had met Pinkett when she auditioned to play the part of The Fresh Prince’s girlfriend. Ironically, she didn’t score the part: she was deemed too short. They kept in touch, however, and started dating after he had separated from Zampino, eventually marrying on New Year’s Eve 1997. By the year 2000, they had started a family, welcoming a boy, Jaden, and a girl, Willow.

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While Pinkett was establishing the beginnings of a future with Smith, Shakur’s life was taking a different turn. He released his debut solo album, 2Pacalypse Now, towards the end of 1991. It has since been hailed as an inspirational record for rappers including Eminem, Game and Nas. A politically-aware second solo album, Strictly 4 My N.I.G.G.A.Z…, dropped in 1993. It was to go platinum.

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But it was with his third and fourth albums that Shakur’s genius was considered to have been fully realized. Me Against The World and All Eyez On Me have been hailed as two of the most influential records of their genre – ever. At the same time, the accomplished actor starred in several acclaimed movies, including 1993’s Lucky with Janet Jackson.

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Remarkably, one of his artistic successes was to happen without him actually being present. Me Against The World was released in 1995, while Shakur was in jail serving a sentence for sexual assault. It reached number one, making the rapper the first artist ever to top the charts while incarcerated.

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Shakur’s music transcended boundaries, and All Eyez On Me was the first hip hop targeted at the mass market, not just die-hard rap fans. By 1998, it was confirmed as having gone platinum no fewer than nine times. The artist’s fifth album, The 7 Day Theory, was released in 1996. Once again, it smashed the charts and it has since been hailed as one of the best hip hop albums of all time.

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Sadly, the album was to be his last. On the evening of September 7, 1996, at the age of just 25, Shakur was fatally shot in Las Vegas, Nevada. The gunman, who was believed to have been in a white Cadillac, was never identified. For Pinkett, it must have been the ending she’d feared for the icon.

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Now named Pinkett Smith, the star has talked about her relationship with Shakur. In 2017 she admitted in a radio interview that despite the fact she was now a well-loved actress and mom, when she first knew Tupac her life had been very different. She even described how, when she met the rapper, she was dealing drugs herself.

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“One of the things that’s very interesting that I’ve never really said before, is that when I first met Pac, when we first met, I was a drug dealer,” she told Sirius XM’s Sway in the Morning. Yet while she managed to turn her life around, unfortunately opposing forces seemed to be at work for Shakur.

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“As I was coming out of the life, he was coming more into the life,” she told the hosts of the morning show in an emotional chat. “I was coming out, he was going in, there was a point at which we met and then we were kind of going our separate ways.”

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There’s no doubting the depth of feeling the two felt for each other. Shakur wrote the poem “Jada” as part of his The Rose That Grew From Concrete collection between 1989 and 1991. In it, he wrote, “U will never fully understand/How deeply my heart feels 4 U/I worry that we’ll grow apart/and I’ll end up losing u/U Bring me 2 climax without sex/and u do it all with regal grace/u R my Heart in Human Form/a Friend I could Never replace.”

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It was a relationship that Pinkett Smith’s husband was to have a lot of – perhaps understandable – insecurity about. In a recent interview on The Breakfast Club radio show, Smith was asked by host Charlamagne tha God, “Were you ever jealous of the love Jada had for Tupac?” Smith’s answer was nothing less than emphatic.

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“F*** yeah! Dude, you know that…was like 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, ‘cos they grew up together and they loved each other, but they’d never had a sexual relationship.”

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Smith continued with his candid explanation, “But they’d come to that age where now 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!”

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The actor even went on to reveal how his wife had urged him to get to know his imagined rival, but he couldn’t bring himself to offer the hand of friendship. “So it was just like I never could… we were in the room together a couple of times, I couldn’t speak to him.”

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Smith admitted, “You know he wasn’t going to speak to me if I wasn’t going to speak to him!” At this revelation, Charlamagne da God seemed incredulous – maybe in part because of Smith’s normal confidence and friendly demeanor. “Really, y’all have so much in common!” the breakfast DJ countered to the star.

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Smith agreed, commenting, “That’s what Jada was saying all the time. Like, ‘I’m telling you, y’all are so similar, you will love him,’ and I just never…that was a huge regret of mine. I couldn’t handle it. You know, I was the soft rapper from Philly and he was Pac.”

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The actor summed up his open and honest divulgement with the admission, “I was deeply, deeply insecure and I wasn’t man enough to handle the relationship.” Video of the chat was posted to The Breakfast Club’s Instagram account where Smith garnerned respect for his honesty.

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Instagrammer djmon305 posted, “Wow it takes a real solid man to come clean about himself like this.” And journeyjustbegun wrote, “Mad respect,” while hot_damn_its_flame4 commented, “The honesty makes him everything.” Meanwhile da_ulimat3 wrote, “Charlemagne ask the toughest question of his career & Will answered it openly & honestly! Kudos Bro…”

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One contributor though, lamented the fact that Smith hadn’t been able to open up like this to TuPac while he was still alive. Instagrammer sandiego_diva wrote, “Damn, I love the way Will Smith opened up to us about his insecurities where Pac was concerned. It’s just sad that it took 20 years for him to admit that he felt a way about Jada & Pac’s relationship.”

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Perhaps the Hollywood A-lister’s honesty will lay to rest the speculation over Pinkett Smith and Shakur’s relationship. Undeniably it’s one that has been much talked about – and evidently, incorrect conclusions have been drawn. Indeed, the actress was upset by how their relationship was portrayed in the movie based on his life, All Eyez On Me.

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The biopic was released in June 2017, on the day the rapper would have turned 46, had he lived. But Pinkett Smith sent out a series of furious tweets in response to what she claimed were inaccuracies in the motion picture. She called the “reimagining of their relationship” in the movie “deeply hurtful.”

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“Forgive me…my relationship to Pac is too precious to me for the scenes in All Eyez On Me to stand as truth,” she said. In one of a series of follow-up tweets, she wrote of the scene where Shakur reads her the poem “Jada”, “Pac never read me that poem. I didn’t know that poem existed until it was printed in the book.”

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And in Pinkett’s chat with SiriusXM, she said, “Pac and my relationship was about survival. That’s how it started. I know that most people want to connect with this romance thing, but that’s because they don’t have the story. It was based in survival. How we held each other down.”

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It isn’t the first time she has challenged misconceptions of their relationship. In a 2015 interview with shock jock Howard Stern, she dismissed claims that their bond was sexual. Indeed, in a bid to test if they could be attracted to each other, Pinkett even demanded that Shakur kiss her.

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Pinkett Smith described that fleeting meeting of lips as the “most disgusting kiss” – both for her and the hip hop legend. So Smith’s discomfort at Shakur’s special bond with the movie star’s wife appears to have been based not on sexual jealousy, but rather their deep emotional connection. And that particular raw nerve is still apparent almost 25 years after Tupac’s death.

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Signing off her storm of tweets about All Eyez On Me, Pinkett Smith wrote, “Happy birthday Pac, you are cradled in my heart for eternity. I love you. – Jada Pinkett Smith (@jadapsmith) June 16, 2017.” It’s clear that there’ll always be a special place in Pinkett Smith’s affections for Shakur. And it seems this is also something her husband is now coming to accept.

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