The 1996 murder of Tupac Shakur can have a sense of the inevitable about it.
"He's blowing past all the stop signs," Allen Hughes, Emmy-nominated director and executive producer of the FX documentary series Dear Mama, told E! News in an exclusive interview, "and it's a moving train wreck at a certain point. It's heartbreaking."
At the same time, Tupac's violent death at 25—even when viewed through the prism of all the beefing and erratic behavior that make his legacy so complicated—was still wildly shocking.
"When he lost his life," Hughes said, "that was the first time people were like, 'Oh, s--t, this is real.'"
Though gunfire made headlines, the battle of words between rappers and their often sprawling cast of associates had for the most part remained just that. And there had always been a sense of the performative about these hip-hop feuds, which the Menace II Society director compared to professional wrestling.
"Even though they're emotional," Hughes explained, "it's still WWE action. But then with a lot of the labels at the time, the streets started coming into the suites, art was imitating life and that line started to blur, big-time. And keep in mind, no one had been killed up till that point. So it wasn't a reality that this was a reality."
But that's not to say Tupac, who had recovered from being shot in 1994, didn't already see himself as living on borrowed time.
"When I heard 'Hit 'Em Up' before he died," Hughes said of the brutal diss track released June 4, 1996, featuring Tupac going hard on onetime friend Notorious B.I.G. (whose murder six months after Tupac's also remains unsolved), "I knew he wasn't gonna be around. You can hear it, he's taking this to another level."
And the filmmaker still regrets never reconciling with Tupac in person after their own creative partnership unraveled 30 years ago.
"We loved hard for like a year and we were gonna do everything together," the now 51-year-old auteur recalled of the time when the Hughes Brothers (as he and twin brother Albert Hughes were credited) directed two music videos for Tupac in 1992 and were working on a third when an argument turned violent.
"What happened at the end, we were both very passionate, highly charged individuals—and my brother as well," Hughes said. "So it makes sense it kind of went like that."
Shakur ended up sentenced to 15 days in jail for his involvement in what Hughes described in Dear Mama as a rather unfair fight, the director briefly appearing on camera to reminisce about the incident.
"For the record," he said in the series, "Tupac didn't beat me up. Ten other motherf--kers beat me up." ("That's when n---as had posses," cracked Snoop Dogg, one of a number of Tupac's friends, family members and fellow artists interviewed in Dear Mama.)
Unfortunately, Hughes told E!, he and Tupac never spoke face to face again. He points to Tupac's 1995 sit-down with MTV News' Tabitha Soren—"Dissing the Hughes Brothers, I wish I hadn't done that"—and the prison interview the rapper gave to Vibe in which he said he "was apologizing" as signs they would have made up.
Hughes said he didn't even know until nine months ago, from reviewing all the raw footage, that Tupac had also told Soren he'd love to work with the Hughes Brothers again, if they'd have him.
"My biggest regret," he said, "was I wasn't man enough—even though he was in the wrong about the situation—to go see him in prison. I would've had a captive audience."
Hughes' own history with Tupac admittedly factored into his initial ambivalence about whether to do the docuseries at all, wary of the inevitable moment he'd become part of the story.
But ultimately, he said, a perfect storm of political, cultural and personal upheaval converged to make it exactly the right project for him.
Hughes was first approached about the series in 2018, when he was already grappling with the divisive political climate and resurgence of racist rhetoric in the public arena. And Tupac's mother, Afeni Shakur, who died in 2016, had been a member of the Black Panther Party, probably one of the most controversial—and misunderstood—organizations in American history.
"They believed in a rainbow alliance, they knew how to bring people together," Hughes said. "I'm that guy, I don't want to be disenfranchised from any culture."
But after current events started "making racism pop" again, he continued, "I'm back in therapy with that s--t."
Then along came "the perfect vehicle to explore all this stuff," he said, "and figure out, 'What is it that I can do? What can we do to shed light on what this condition is? Why are we like this? Where did this come from?' I had all these questions."
So Hughes dove in, thinking "this'll be three years of my life that I can devote towards exorcising this anger—poetically, artistically, creatively—through Dear Mama."
To be clear, though, he stressed, he was motivated because he was appalled by the division he was seeing.
"I believe in all of us doing this together," he said, "and I didn't like that feeling."
He was also reminded during the making of the series that "you're never at the top of the mountain," that the fight for civil rights, women's rights, human rights "is an eternal struggle," he said. "And I was naïve enough to forget that."
Weaving Tupac's story with Afeni's—they both contained multitudes, to say the very least—Dear Mama busts the myth of "two Tupacs," the charismatic poet raised by a radical feminist vs. the volatile face of small-t thug life who was arrested half a dozen times and spent eight months in prison after being convicted of sex abuse (charges he vehemently denied).
"What stayed with me, knowing Tupac," Hughes said, "was the sense of compassion I have for him and his journey now that I just didn't have before. I see the inherited trauma he's born into. I see the expectations the Black Panther Party, his mother had for him. I see what poverty does to the psyche of a young poet."
The prolific rapper and up-and-coming actor, who didn't live to see several of his films come out, basically spent his short adult life torn between the man he thought he was supposed to be and the rock star he was, with all the excesses that entailed.
Growing up with a single mother who accomplished so much as an activist but struggled to keep her household together taught Tupac to revere and protect women, but empowerment anthems were on a downswing and gangsta rap was on the rise when he signed his first record deal. "So there's always that conflict in his journey as an artist," Hughes said. "The toxic masculinity of hip-hop at the time, he was always struggling with it."
He was also the consummate performance artist who fully inhabited whatever character he was playing at any given time, be it fiery revolutionary, mama's boy or millionaire playboy rapper.
"His gift was the power of that transcendent charisma and passion, and anger and love and joy and pain," Hughes said. "All of it with Tupac was like a 10."
Dear Mama is streaming on Hulu.