Biggie’s Crown and Tupac’s Love Letters Highlight Sotheby’s Epic Hip-Hop Auction

The international auction house's first foray into hip-hop opens in Manhattan on Sept. 15

September 11, 2020 8:05 am
Created by DJ Ross One, The Wall of Boom (estimate $70-$100,000) is an art installation that features 32 vintage boomboxes.
Created by DJ Ross One, The Wall of Boom (estimate $70-$100,000) is an art installation that features 32 vintage boomboxes.

Unique artifacts, artwork and other items with deep ties to a style of music that was born on a block in the Bronx in the ’70s are set to cross the block at a Sotheby’s auction in Manhattan later this month.

Being held starting September 15, Hip Hop features more than 120 lots that celebrate the history and cultural impact of the style of music DJ Kool Herc is credited with birthing at a party at 1520 Sedgwick Avenue in 1973.

The first ever dedicated hip-hop auction to be presented at a major international auction house, Hip Hop features lots including the crown the Notorious B.I.G. wore in his 1997 “King of New York” photograph (estimate $200,000-$300,000), an archive of high-school love letters written by a teenage Tupac Shakur ($60,000-$80,000), Salt-N-Pepa’s “Push It” jackets from their 2015 Geico Super Bowl commercial ($8,500) and DJ Ross One’s Wall of Boom, a working art installation featuring 32 vintage boomboxes ($50,000).

The crown worn by The Notorious 1997.

In addition to physical items, the auction is also offering up one-of-a-kind experiences with industry legends like a “Sweat The Technique” lyric writing lesson with The God MC Rakim Allah and a virtual wine tasting with Big Daddy Kane.

Organized by Sotheby’s VP and senior specialist Cassandra Hatton in conjunction with former Tommy Boy Records president Monica Lynch, Hip Hop mostly features items that were consigned directly by artists or their estates, and a portion of the proceeds will benefit the Queens Public Library Foundation as well as Building Beats, a non-profit that teaches life skills to underserved youth through DJ and music programs.

As Hatton explains to InsideHook, she’s been trying to put together this auction for nearly a decade for a very simple reason: she loves hip-hop.

Salt-N-Pepa’s “Push It” jackets.

“If you look at all of the sales I do, they also focus on things that I personally am passionate about. I do sales on space exploration, I do sales on the history of science and technology. I decided a long time ago I would only handle things I really liked,” Hatton says. “That is part of why I decided to do a hip-hop sale. Everybody loves hip-hop, it’s huge. Hip-hop is an international cultural phenomenon. So, I knew, at least from a commercial sense, there would be a lot of clients out there. That’s a consideration when you’re putting together an auction. I mean, I could also have a passion for knitting needles. Nobody’s going to let me do an auction on knitting needles.”

Though all the lots in the auction have sales estimates, Hatton acknowledges it was really difficult to guess at how much value clients would place on items that had never been sold before.

“I think the estimates on the majority of the items in the sale are on the conservative side. It’s important to have estimates be conservative because you are waiting for the buyers to tell you what the value is, and you want to have as many people participating as possible,” she says. “I think they all have the potential to do much better than their estimates. When you look at jewelry and gold, those have inherent value. But these items, the value isn’t coming from the material they’re made of, it’s coming from the symbolism and the story behind them. I think all these items have really fantastic stories. So, I’m excited to see who agrees with me.”

Tupac Shakur’s high school love letters.

It will be particularly interesting to see how one of those items, Biggie’s crown from his final photoshoot, does with bidders.

“It’s just a plastic crown, but there’s this symbolism of turning this young, talented man into a king, into royalty. I think is a very powerful thing,” Hatton says. “It’s one of the most recognizable items in the history of hip-hop or in music period, right? Everybody knows this item. Normally I don’t do this, but I looked back at comments on different articles that have been written about the crown. Some people say it’s the Mona Lisa of hip-hop and it belongs at the Smithsonian. Other people going say it’s just a trashy piece of plastic. It’s so bizarre to see that huge gulf in opinion because, for me, it is a symbol of a movement that has gone on to be a powerhouse in terms of cultural influence. That’s what that crown means to me.”

The love letters from Shakur are also one of Hatton’s favorite items.

“They’re so sweet and so disjunctive with what the public image of someone like Tupac is,” she says. “People think of him as this hard gangster rapper, but I’ve seen several letters he wrote and he really was a sweet, respectful young man. Some of the content of the letters is racy. I definitely blushed while I was reading some of them, but you could see that even at the age of 16, he was already a star. He was already there. It’s really interesting to be able to see things that let peek into the life of someone before they really hit it big.”

To schedule an appointment to view property from the sale, contact

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