Auction Results: Sotheby’s Hip Hop Sale

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Memorabilia representing Biggie Smalls, Tupac, Salt-N-Pepa, and others realize high results

Crown worn by Biggie Smalls during “King of New York” photoshoot. Photo by Angela Weiss/AFP via Getty Images.
Crown worn by Biggie Smalls during “King of New York” photoshoot. Photo by Angela Weiss/AFP via Getty Images.

The crown worn by Biggie Smalls for the “King of New York” cover photo highlighted Sotheby’s inaugural hip hop sale last week. Taken three days before he was shot and killed, the image remains a testament to Biggie’s power and the void left in his absence. The crown came to auction with an estimate of USD 200,000 to $300,000 and sold for nearly double the high estimate at $594,750. 

The lot was emblematic of an overall strong auction for Sotheby’s. Many of the highlighted lots crossed the auction block at or above their high estimate. “Achieving an overall total of $2 million, the auction was a celebration of the history and cultural impact Hip Hop has had on art and culture,” said Sotheby’s on their official Instagram page shortly after the sale.

Love letters written by Tupac Shakur to a high school sweetheart were another featured lot. They offered a look into the rapper’s psyche in his late teenage years, including his fear of rejection. “I just want to be less sensitive and less of a pest,” he admits in one letter. The lot realized $75,600, on the high end of its $60,000 to $80,000 estimate.

Tupac Shakur letter from Clinton Correctional Facility. Photo by Sotheby’s.
Tupac Shakur letter from Clinton Correctional Facility. Photo by Sotheby’s.

Another letter written by Tupac nearly beat its high estimate sixfold, selling for $17,640 against a $2,000 to $3,000 estimate. Tupac wrote this letter while serving a sentence at Clinton Correctional Facility at the age of 24. Describing a date he had with the letter’s recipient before incarceration, Tupac’s fear of rejection appears once more. “I was so nervous around u constantly in fear of Saying or doing the wrong thing,” he writes. “It was a comfort to hear i didn’t ruin my first impression of me to your eyes!”

Representing Salt-N-Pepa in this sale was the group’s leather jackets, worn for a performance of “Push It.” These were not, though, the original jackets worn during performances of the popular single in the 80s. Those were stolen from the group’s dressing room decades prior. 

In 2015, Geico decided to do a “Push It”-themed commercial for that year’s Super Bowl. The original jackets’ designer, Christoper “Play” Martin, was tapped to make faithful reproductions. He recalls in a Vogue interview the all-nighter he needed to pull to create the new pieces. Two of the jackets from the Geico commercial were estimated to sell for $12,000 to $18,000 and realized $23,940 at the Sotheby’s auction.

Salt-N-Pepa “Push It” jackets. Photo by Sotheby’s.
Salt-N-Pepa “Push It” jackets. Photo by Sotheby’s.

Encapsulating much of hip hop history, DJ Ross One’s installation of retro boomboxes, named The Wall of Boom, sold for $113,400. That was $13,000 above the high estimate. Among the notable boomboxes in the installation are two JVC M90s, which are especially loud boomboxes popularized by hip hop artists like LL Cool J and the Beastie Boys. 

The Beastie Boys were also represented elsewhere in this sale. A Licensed to Ill Tour concert poster from 1987 was made available. Licensed to Ill was the Beastie Boys’ inaugural album. Revisiting it years later, music critic Gwen Ihnat noted the group’s “brashness—an almost unhinged confidence that this record will be one for the ages.” The poster’s sale at $3,528 doubled the high estimate of $1,500.

View each lot alongside the price realized on Sotheby’s website. Those interested can also learn more about the event from Auction Daily’s presale coverage.