Supreme Marvin Gaye T-shirt.

When Guillermo Andrade, the designer behind streetwear brand 424, sat down with buyers from Barneys New York, they asked him which artist he wanted to collaborate with the most. He immediately said Tupac, and because the multihyphenate entertainer is no longer alive, everyone in the room had a bit of a laugh. But a few weeks later, Andrade received a call from the team at Barneys saying they could make it happen — sort of. Because of Barneys’ relationship with Bravado, which has the global apparel rights for Tupac, Andrade could collaborate directly with the late rapper’s estate to conceive a collection that would be sold exclusively at the department store.

“I was more excited than anything else,” said Andrade, who grew up in Guatemala and moved to the U.S. as an undocumented immigrant in 1993. “For a person with my background and where I come from, the possibility to be associated with the Tupac estate was a big crazy win on a personal level.”

Andrade met with Bravado and they connected him with Tupac’s estate. He recalled them as a warm group made up of Tupac’s friends and family who wanted to protect his image and honor his legacy. They let Andrade try on Tupac’s jewelry and study his beloved hockey jerseys and custom-made pieces by Gianni Versace. He presented his sketches to Tupac’s aunt, Gloria Cox, who approved of the work. She told Andrade they reminded her of Tupac’s own sketches — before he died he was working on a clothing line with his then girlfriend Kidada Jones.

A portion of the collection was released at a Barneys The Drop event in Los Angeles last year. Andrade designed graphic T-shirts intersecting 424 with a raised fist and “2Pac,” a leather trucker jacket and matching pants informed by Tupac’s love of the rich, sumptuous fabric, and shirts with Versace-esque scarf prints.

424 x Tupac at Barneys The Drop

424 x Tupac at Barneys The Drop. 

Andrade’s collection didn’t use any photographs of Tupac, but with the rise of merch and streetwear, the fashion industry’s continued obsession with the Nineties, and designers’ political awakenings, more and more brands are using images of important black and brown personalities on apparel. It’s not a new thing — the streetwear line PNB Nation did this often during the Nineties — but as of late it’s been more pronounced.

Kith recently released a “Poetic Justice” capsule that features an image of Tupac from the 1993 movie — Kith worked directly with Sony Pictures and Tupac’s estate declined to say whether or not it was involved in this collaboration. This month R13 released a Notorious B.I.G. collection. And, in December, Supreme dropped a Marvin Gaye T-shirt — over the years Supreme has displayed everyone from Sade to Michael Jackson to the actual Supremes on its boxy T-shirts. Even Fashion Nova is selling tops with images of Aaliyah, Jay-Z and Biggie, while emerging streetwear brand Strange Fruit places mug shots of Huey P. Newton and Snoop Dogg on track pants.

But who should be making money from clothing covered with black or brown artists?

In 2017, when Kendall and Kylie Jenner promoted a line of band T-shirts that placed their faces over pictures of Tupac, Biggie, Kiss, Ozzy Osbourne and others, the public got a glimpse of how merchandise bearing images of artists — specifically dead ones — works.

In order to sell a piece of clothing featuring a photo of Tupac, for example, the company must acquire a license that covers likeness rights, which are owned by the estate, and copyrights, which are typically owned by the photographer. While copyrights are instituted globally, postmortem likeness rights vary from state to state. The Jenners neglected to go through any of these channels so they were sent cease and desist letters and sued by various parties. They eventually pulled the shirts and settled with all involved entities out of court.

Jeff Jampol, the president of Jampol Artist Management, an agency that manages the estates of artists including Janis Joplin, Otis Redding and Jim Morrison, was one of the parties that sued the Jenner sisters. Jampol still seems aggrieved by the act: “The dirt under Jim Morrison’s fingernail can wipe the floor with their credibility,” he said over the phone. But he also offered that it’s his job is to introduce his clients to a younger demographic or a new fanbase, who probably follow the Jenner sisters on Instagram.

“I’m trying to figure out what that magic is about my client and I have to present that in ways that are credible and authentic to people who are 11 to 30 years old,” said Jampol, who noted that streetwear has been a vehicle for that. “Older fans have the album. They have the T-shirt. They went to the concert. I’m looking for new fans.”

This also seems to be Bravado’s strategy with the Tupac apparel collaborations. Before her death, Tupac’s mother Afeni Shakur granted executor rights for the estate to Tom Whalley, a veteran record executive who signed Tupac to Interscope Records — Whalley declined to be interviewed. Over the past few years, Bravado has created cobranded Tupac apparel with 424, Trapstar, Vfiles, Marvel and Vlone. The Vlone tie-up was probably its most ambitious effort to date since it paired a pop-up shop of merchandise next to Sweet Chick, a chicken-and-waffles spot on the Lower East Side that was converted to Powamekka Cafe, a restaurant Tupac envisioned and sketched while in jail.

R13 x Notorious B.I.G. capsule

R13 x Notorious B.I.G. capsule. 

Jampol views apparel collaborations as a legacy exercise first, a marketing one second and a revenue generating one last.

“I’m not looking at how much money can I make. I’m looking at how a T-shirt will feed into 20 or 30 different other areas relating to my client,” he said.

But there is money being made from the category, especially as such merchandise aligns with fashion and is no longer confined to concert venues, hip-hop centers itself as pop, and more agencies like Bravado emerge. The Thread Shop, which sits under Sony Music Entertainment, was formed in 2009 and handles merch for clients including Nas, A Tribe Called Quest, Big Pun and Miles Davis.

How much money this product makes varies per artist — Jampol noted that although The Doors have sold more records than The Ramones, they undersell them significantly in terms of apparel — but industry sources say the estates usually make 10 to 20 percent of wholesale for merchandise partnerships.

Chi Modu, the photographer behind iconic images of Tupac, Biggie, Nas and others, says he’s getting the least. When he was taking these photographs, hip-hop was considered a niche music category and publications weren’t concerned about image copyright. But he knew they would be valuable one day and made sure to own all of his images.

A lot of Modu’s licensing deals are with TV networks that use his photographs for programming, but he has worked with manufacturers like Bravado, which he had to sue in 2017 for using images of Tupac on T-shirts sold in Macy’s and Urban Outfitters beyond the license expiration date. He thinks the current photo licensing and merchandise model is broken and in order to fix it he’s taken all of his images offline, which means all of his license contracts for apparel collections expired in December 2018.

He’s hoping that by not having his images in the market, it will force manufacturers to create better contracts. But he would also like to reduce how much middlemen like Bravado and Remyrylie, which handles the apparel licensing for Biggie and lost the Tupac rights to Bravado, are taking from these deals.

“I’m compensated a flat fee for the license and that’s it. Some people can attach that to royalties, but manufacturers fight aggressively against that,” said Modu. “I make substantially less — less than a quarter of what these companies are making.”

Modu believes he should be working directly with the estates or the likeness rights holder, which he’s trying to foster with Full Frame Agency, and splitting the profits (minus production and miscellaneous costs) with the likeness right holders.

“The photograph of the artist is driving the sale of the T-shirt,” said Modu. “I wasn’t just there — I was taking a picture and projecting how I saw that artist to the world. The beauty of someone in my position is that this is money you won’t make without me because I won’t let you access the photographs. If you are a smaller brand using the images in the name of creativity, I don’t mind. But if you are trying to mass produce something, please cut me in.”

Fashion Nova x Poetic Justice

Fashion Nova x Poetic Justice 

But beyond the legalities and the economics of using this imagery, there are questions around if some of these tie-ups make sense creatively or philosophically, and if the execution properly honors the artists’ legacy.

When Tupac was alive, he made a concentrated effort to wear black-owned streetwear brands including Karl Kani — at the  height of his career, Tupac didn’t charge Kani to appear in his ad campaign because he was black — and Walker Wear, a line founded by April Walker, who also created custom pieces for Tupac to wear in the 1994 film “Above The Rim.”

“I have my opinion and I respect the opinion of the estate, but I think it’s been a little diluted over the years,” said Walker. “Someone else has control of the estate who doesn’t have the same vision that Tupac had and that’s when things get lost in translation and it leaves room for culture vultures.”

Kani had similar things to say, mentioning that companies have watered down Tupac’s imagery. They also both agreed that if any company affiliates itself with Tupac in a commercial way, proceeds should go toward one of the causes he championed when he was alive.

“You have to tie it into something that we know is close to Tupac’s heart,” said Kani. “He was talking about police brutality and jail reform in ’95. Donate something to those causes. If people are just using it to put money in their own pockets and not pay homage, it ain’t real.”

Kith x Poetic Justice

For Jampol, when deciding who his clients should co-brand with, he’s trying to achieve parity to ensure that both his artist and the company he’s working with are elevated by the partnership. Jampol said that Supreme, which he’s worked with before, offers that. He described the company as the “coolest of the cool” and explained why a Supreme Marvin Gaye T-shirt makes sense.

“Marvin Gaye was f–king cool. Just think about Motown and him coming out with ‘What’s Going On,’ and telling Berry Gordy to f–k off because he wanted to sing about what’s going on in the streets,” said Jampol. “And when Supreme is lying in the gutter 10 or 20 years from now, Marvin Gaye will still be soaring above the planet being iconic, special and radiant. Supreme understands that and that’s why they put him on a T-shirt.”

Supreme has been challenged about its execution around placing artists on T-shirts, which some call lazy because, they claimed, it’s usually just a screen printed T-shirt with little creativity. During interviews, the same was mentioned about Kith’s “Poetic Justice” capsule that was also a screen printed T-shirt with “Kith Just Us” sitting above Tupac’s head.

“People just take the lowest hanging fruit. They settle for average or OK content and not the content that shows they really believe in the artist as opposed to just wanting to profit from their name,” said Modu. “People have to be careful with ‘Pac because he’s bigger than whatever simple idea you have.”

Awake NY Michelle Obama T-shirt

Awake NY Michelle Obama T-shirt. 

For his Awake NY line, Angelo Baque, who used to work for Supreme, has featured Frida Kahlo, Gil Scott Heron, John Coltrane and Michelle Obama on T-shirts. He feels privy to using this imagery based on his staff, his background and his intentions.

“Since I’ve moved forward with Awake, I’ve tried to use this platform to educate our kids on what’s going on socially and politically, so using someone like Michelle Obama was important to me because Barack is the obvious choice,” said Baque. “But when I was growing up, my mother ran the house and even within my company, my right and left hands are women. I don’t know any other streetwear brand that has this kind of structure. These kids are smart nowadays and they will call bulls–t on any brand that throws black or brown imagery on a T-shirt, but isn’t donating anything to charity or employing people of color.”

Andrade from 424 is still sitting on the second half of his Tupac collaboration and he keeps in touch with the estate. He’s hoping to do a capsule project connected with Tupac at some point. According to Andrade, anyone, no matter what race, age or sex they are, should be able to use the imagery as long as they are being thoughtful about it.

“You can’t tell someone who they can and can’t be inspired by. And we live in a different time now where it’s possible that a 12-year-old white kid loves only rap and is motivated by the people he listens to,” said Andrade. “But I do think we should all have more sensitivity about how we make money off these artists.”

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