Tupac Shakur and filmmaker Allen Hughes will forever be intertwined. Hughes and his twin brother, Albert Hughes, directed Shakur’s first video, for 1991’s “Brenda’s Got a Baby,” when they were just teenagers. Their creative relationship flourished and the trio continued pumping out projects together.

But that all changed in 1993. Following Shakur’s breakout role in Juice, the Hughes brothers recruited him to star in their inaugural film, Menace II Society. By then, Shakur was a bona fide rap star and Allen noticed he’d become “unpredictable.” His volatility ultimately forced Allen to fire him. In retaliation, Shakur and nearly a dozen gang members attacked Allen, leading to a two-week stint in jail for Shakur. Despite a public apology, the two never spoke again. Shakur died three years later.

Allen says he loved Shakur and deeply regrets never having made peace. Perhaps as an amends of sorts, he took on the daunting task of telling the stories of Shakur and his mother, former Black Panther Afeni Shakur, in the FX series Dear Mama. The five-part documentary, which was nominated for a 2024 Grammy Award for Best Music Film, illustrates the fragile relationship between mother and son and shines a light on the injustices they faced not only as Black people but as public figures.

Allen spoke to HITS about the Grammy nomination, what made it particularly meaningful and his biggest regret.

Were you surprised when you got the Grammy news?

It was a surprise. We were blessed to win in 2018 for The Defiant Ones [Hughes’ HBO docuseries tracing the careers and relationship of Dr. Dre and Jimmy Iovine], so I was thinking all week that the nominations were going to be announced, but for some reason, that day it slipped my mind. Then my phone… I was thinking someone had died the way my phone was stacking up… and I was, like, “Oh!”

When any bit of good news comes in related to this project, I talk to Tupac’s aunt, Glo, Afeni’s sister. She’s featured prominently throughout the film, and she’s just the best. So I’ll take any excuse I can get to talk to her and celebrate. I usually get to have an hour conversation. It makes me so happy and thankful to share these things with her because for so long after Tupac’s passing, there were stages of mourning and people misunderstanding things. Now, to see the matriarch of the family have a sense of completion is so rewarding. It warms my heart.

I can imagine, then, that this nomination is particularly meaningful to you.

It’s probably the most meaningful thing I’ve worked on since Menace II Society. What it’s saying, the theme of the relationship between these two characters, especially the rich social-justice narrativeâ€•they’re fighting for human rights, women’s rights and obviously for Black people in the Black Panther organization… There’s so much on Afeni’s side that was just erased or forgotten, so that’s why it’s so rewardingâ€•to bring her narrative, that struggle and her role in that movement, to the forefront of the culture. When you look at Tupac, you see, “Wow, the fruit doesn’t fall far from the tree.”

Knowing Tupac personally and having a creative relationship and friendship, too… I thought The Defiant Ones was personal, but this one’s really personal.

From “Changes” to “Brenda’s Got a Baby,” how involved were you in selecting the songs that went into each episode?

I’m the one who’s gotta select them. God bless the estate and the family because they never forced me to do anything.

The hits are in there, but between my lead editor, Lasse Järvi, and me… What I love about Lasse is that he likes obscure things. He wanted to put [Tupac’s song] “Troublesome ’96” in The Defiant Ones. I’d never even heard “Troublesome ’96.” Sometimes Lasse will find a diamond in the rough, though sometimes it’s so rough around the diamond that I’m, like, “Nah.” But there is that rare case when he finds something, and I’m, like, “Let’s give it a whirl.” Mostly, we discuss the things I want to put in the movie. I’m very musical—I don’t play any instruments, but I’m very into music.

When you revisit “Brenda’s Got a Baby” in the film, I was blown away by how insightful Tupac was as a teenager. Have you ever encountered another MC like that?

Hell no! “Brenda’s Got a Baby” came out when he was 20, and he wrote it when he was 18. To this day, point me to one male rapper who consistently writes female-centric songs. What makes that song unique is that it’s one long verse. It’s storytelling at its finest.

At one point, you step in front of the camera.

Which I never wanted to do. My partner and producers were, like, “You gotta do this.” But I was, like, “How does it look, me directing this and then doing a formal interview?” That’s why it was cool when Atron Gregory, Tupac’s first manager, was, like, “Sit down and get in the hot seat!” We were just joking. Then, all of a sudden, it gets serious. I got bamboozled! But it was genuine.

Considering your history with Tupac, was there ever any doubt that you were the one to tell this storyâ€•or does that history make you the perfect person to tell it?

The family wanted me to do it, so the only doubt came from me, because there are some rabid fans who are pretty crazy because of the altercation, and they’re a little prejudiced. I was apprehensive at first, but now I see, and Glo always reminds me, “You are the perfect person given your history and where your heart is.” You want it to hit home with people not because of the tragedy [of Tupac’s death at age 25] but because you want the relationship with his mother to be the universal thing people connect to, even outside the song “Dear Mama.” You’ve got to be really mindful about making it a universal story. The dynamic of the relationship is universal, and that’s a difficult thing to achieve on film.

Is there anything you’d have done differently with Tupac?

I would have gone to see him in prison [Shakur served 11 months on sexual abuse charges but was released in 1995 pending an appeal of his conviction]. Because, funnily enough, I would have had a captive audience. We were so young—I just think it would have been the mature thing to do. I wish I would have gone and seen him. That’s the big regret.

You’ve said you didn’t know until this year that Tupac said some nice things about you in the 1995 interview he did with MTV’s Tabitha Soren. What was your reaction to that?

I felt like an idiot for being so immature. What it showed me was like with brothers, like with any youth, you gotta fight, and sometimes it’s going to be a fistfight. But you can’t let that be the thing that makes you never talk again. The family reminded me over and over, to know Tupac and to love Tupac was to fight with Tupac.