Rapper Dads and Their Rapper Sons Talk About the Family Business

Photographs courtesy of subjects, Getty Images; Collage: Gabe Conte

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When he was 16, Demetrius Gray, the son of multi-platinum rapper Juvenile, had a very clear birthday wish: he wanted his father to buy him a 1971 “Glass House” Chevy Caprice. Instead, the New Orleans superstar gave his son—now better known as Young Juve—a new Apple laptop, Pro Tools, and a few pieces of recording equipment. At the time, the teenager was disappointed, but that decision wound up not only changing his life, but also his relationship with his father.

“I was mad as hell,” Young Juve says. “I wanted what I wanted, [in the end] I got what I wanted, but I ended up getting it on my own.”

Juvenile and Young Juve are just two of a growing niche in hip-hop: the father-son rapper tandem. With the genre celebrating its 50th anniversary last year, we’re now in a place where chart-topping MCs from the ‘90s and ‘00s are in their late 40s and 50s, and have raised young men who’ve continued their musical legacy. And in the cases of Juvenile and Young Juve, E-40 and Droop-E, Big Hit and Hit-Boy, and Mac Phipps and Bandana Kin, they’re not just working in the same field but actively working together. It’s certainly different from the usual familial footstep-following, but the artists GQ spoke to approach these situations like any caring, thoughtful parent would.

“I put that extra push behind him once I realized he was serious. And that's what I think all parents [should do],” Juvenile says. “I wasn't behind him the whole while [saying], ‘Man, you need to rap.’ But once he showed me he was seriously rapping, that's when I got really behind him.”

At age nine, Jay-Z and Beyoncé’s daughter Blue Ivy became the second-youngest Grammy winner ever, thanks to her appearance on her mom’s 2020 record “Brown Skin Girl,” but Droop-E began showing up on his father’s tracks at just two years old. 40’s 1992 debut features the interlude “Questions,” in which the pair recreate their usual banter on a car ride to day care.

A few years later, Droop-E would actually rap on his father’s magnum opus, 1995’s In A Major Way. Billed then as Lil E, he appears on “It’s All Bad,” a contemplative track about society, police violence, and systemic racism. (E-40 having his son ask his father to “sprinkle me with more game” is one of hip-hop’s truly perfect moments.) 40 wrote his son’s verse, but the five-year-old nailed it, showing a natural comfort and skill as a vocalist. The pair continue to make music together, though Droop-E has carved out his own sonic niche, from collaborations with Kendrick Lamar to alternative-leaning projects like 2023’s 4005: Lovesong EP. His father, who released 10 studio albums between 2010 and 2013, is one of the most prolific figures in all of music, and that work ethic has inspired Droop-E since childhood.

“He made a statement to me maybe four months ago," 40 recalls. "He said, ‘Pops, ever since I was born, all I’ve ever seen you do was hustle.' I thought about it and realized ‘You fucking right.’”

Young Juve, who attended the music-focused college Full Sail, knows how to produce and mix, and has also been involved in designing merch for his dad. Droop-E serves as president of 40’s Sick Wid It label, and has made beats for not only his father, but Yelawolf, Too Short, and Keak da Sneak, too. Droop-E began working for his dad’s label when he was still in high school, and effectively became its president immediately after finishing high school. Sick Wid It began in 1989, a year after Droop-E was born, and it still stands today as a testament to 40’s singular musical legacy, one that he’s thrilled to have his son shepherding.

“I'm glad this is a family business and he feels right in place, playing this position,” E-40 says. “It means everything to me.”

In the cases of Mac Phipps and Big Hit, making music with their sons has helped them build a bond and make up for lost time. Both artists missed much of their boy’s life due to incarceration, Phipps in a case of wrongful conviction for manslaughter that kept him in prison for 20 years and Hit for offenses like drug possessions that resulted in two decade-plus stints.

Phipps’ case was a high-profile incident of rap lyrics being used as evidence in a criminal trial, and the former No Limit MC does acknowledge that he felt some reservations about his son rapping particularly when he heard some of the “street element” in Kin’s music.

“That's kind of what they used against me in court,” he says. “I don't think it was an overwhelming sense of urgency, but I was just nervous for him because I never wanted him to have experienced [what I did].”

Phipps is a strong supporter of laws that restrict the use of song lyrics in trials, but that campaign is still a work in progress. Still, he loves sharing a passion with his son, and says that Kin’s early music helped him connect to and empathize with the child who was only three months old when his father began serving time.

“It came to a point where when I wanted to understand things about him, I listened to his songs, because he was more comfortable sharing them in songs than he was actually expressing them to me,” Phipps says.

Phipps has obviously shared his own music with his son, and during his time in prison he actually wrote a few tracks intended for Kin, more commercially-minded records he says were designed “for my son to make some money.” Kin, as any normal kid would be, was appreciative of the effort, but wanted to carve out his own artistic identity.

“He'll never steer me wrong. I know whatever he writes, it'll be best for me. But I'm authentic. I like to write my own stuff,” says Bandana Kin.

During his incarceration, Big Hit wrote “folders” full of song lyrics and sent them home. Hit-Boy recalls being just 10 years old, reading songs his father had written about “the court system, and judges, and all this different type of shit that I didn't really understand at the time.”

The two released a couple tracks together back in 2014 before Big Hit’s second sentence began, including the hustling manifesto “Grindin’ My Whole Life." Hit-Boy went on to become one of the defining producers of the 2010s, a Grammy winner who's worked on defining songs by Travis Scott, Kanye West, and Beyoncé. Big Hit says he didn’t grasp the full extent of his son’s success until he was free. Since his release, they've released three albums and plenty of songs, including a record with The Alchemist and Big Hit’s solo debut, The Truth is in My Eyes. It's the continuation of a partnership that was interrupted a decade ago; they're committed to not just recapturing that momentum, but building on it.

“We know this shit needs to be heard and the story is motivating people and we can’t waste no time,” Hit-Boy says. “[I’ve] never seen him for longer than a year on the streets, for my whole life, and that shit is still in the back of my head. That shit's still a true fear.”

It’s worth noting that many of these artist pairs come from cities with robust, storied rap scenes and families filled with musicians. E-40 and Droop-E hail from California’s Bay Area, and 40’s group The Click includes his sister, brother, and cousin. Though Young Juve was born in St. Louis, he eventually moved back to New Orleans and has become ingrained in the city’s vibrant rap scene, scoring several local radio hits and forming close friendships with BG’s son TY and the late Soulja Slim’s son Lil Soulja Slim. (Juvenile actually organized a group called Ghetto Children, named after a 400 Degreez album cut, composed of the trio.) Musically, they do pull from the same sounds that inspired their fathers—classic New Orleans hip-hop in Kin and Young Juve's case, the hyphy sound of the Bay Area in Droop-E's—but they’re far from carbon copies. Juve’s melodic tenor flows are a stark contrast to his father’s gravely bluesman voice, while Kin’s approach is more similar to Louisianans like YoungBoy Never Broke Again or the late JayDaYoungan. Kin embracing that more pained, soul-baring style of rap is understandable, given the challenges he faced quite literally from birth.

“I just wanted the world to know where I come from. I wanted the world to know that I had a father taken away from me, and I wasn't even born. I wanted them to know my life,” Kin says. “I just wanted people to hear me out.”

Thanks to a widely-acclaimed appearance on NPR’s Tiny Desk series last June and an appearance at Coachella 2024 with Jon Batiste, Juvenile is back in the zeitgeist in a way he hasn’t been since the late 2000s. He (and his son) are making the most of their deserved flowers, with a live band tour. It’s a true crowning moment for the pair, whose musical relationship dates back to a 10-year-old Young Juve writing and performing for his father a rap referencing the 30-plus tracks on his UTP: The Movement mixtape. Now, Juvenile says that his son is crucial to keeping his creative flame lit three decades into his career. With his biggest tour in a decade later this year, the “Back That Azz Up” MC explains that he simply couldn’t imagine doing it without his son by his side.

“It was a few years ago when I really realized that, ‘Damn, I need him on stage.’ You don't realize until you do a couple shows and somebody's not there…I missed him and I was like, ‘Goddamn. This shit is real weird without him on stage.” Juvenile says. “He'll tell you right now—I can't perform without him.”

Originally Appeared on GQ