Legendary Biggie Smalls Crown Leads Sotheby's First-Ever Hip Hop Auction

“Every time I thought of Biggie,” Claiborne said in an interview, “I always thought of him as a big, fat West African King. Puffy wasn’t so into it, he kept saying that he worried Big looked like ‘the Burger King.’ So Big was trying to reassure Puffy and it turned out fine.”

It went down as one of the most recognized photographs in hip hop history and one of the strongest representations of hip hop’s infiltration of American visual culture. Three days after the shoot, Biggie was killed. His death cemented the symbolic power of the image, which would be carried throughout Biggie’s funeral procession.

“There are images of black people, rappers or not, that you don’t see in American culture,” said Claiborne. “You rarely seem them as regal.”

Rivaling the crown in symbolism is a trove of revealing and intimate love letters by a teenage Tupac to his high-school sweetheart while at the Baltimore School for the Arts. The twenty-two letters, which realized $75,600, falling within estimates, are an early record of the sensitive, lyrical writing style Tupac would later be known for, and offer a diaristic glimpse into his struggles and aspirations as a budding rapper.

Featuring memorabilia, photography, contemporary art, and one-of-a-kind experiences, from across the highpoints of hip-hop from the 1970s to today, the sale brought in $2 million with a 91-percent sell-through rate.

For Hutton, the auction was a long time coming. “I actually first had the idea for this sale about seven years ago, but it wasn’t until about two years ago when I met Monica Lynch, who is the former president of the very influential Hip Hop label Tommy Boy Records and serves as a consultant on the auction, that the sale started to take shape," she told Art & Object. "From then on the sale really gained momentum.”

Also making a splash was a 12-inch single with original artwork by Jean-Michel Basquiat, Rammellzee vs. K-Rob “Beat Bop,” which sold for $126,000 (on a $2,500 low estimate) making it the most expensive hip-hop vinyl record ever sold at auction.

Salt-N-Pepa’s “Push-It” jackets sold above their estimates for $23,940. Photographs did well too. Chi Modu’s image of Biggie in front of the World Trade Center sold for $30,240 on a $6,000 low estimate, setting a record for the artist at auction. Others by the photographer of Tupac, Eazy E, and Snoop Dogg also outpaced their estimates.

In terms of artwork, DJ Ross One’s installation of thrity-two vintage boomboxes brought in $113,400 (on a $70,000 low estimate), while a limited edition painted cast vinyl and metal sculpture by Daniel Arsham realized $13,860.

The experiences, a special feature of this auction that was slightly unusual for a Sotheby’s sale, fell within expectations or slightly below. An atelier visit with Harlem Tailor Dapper Dan sold within its estimate for $11,340, while a private lyric writing session with The God MC Rakim Allah went for just under its estimate for $18,900. A virtual wine-tasting with Big Daddy Kane didn’t find a buyer.

“I really wanted to include items that you don’t normally find at auction and experiences are not something that are traditionally included in a Sotheby’s sale. The experiences on offer are truly once in a lifetime experiences that you can’t do anywhere else. We’re lucky enough to be working with living legends so including these experiences is way for people to really get close to them.”

The sale comes at a time when auction houses are expanding into new territories for memorabilia related to fashion, music, sports, and pop culture. Just last month, Christie’s sold a pair of sneakers worn by Michael Jordan for a record $615,000, and in May Sotheby’s first set the record for a pair of sneakers with a sale of another pair of Air Jordans for $560,000. Sotheby’s inaugural hip hop auction is likely to see some records as well. 

A portion of the sale’s proceeds will go to benefit the hip hop programs of the Queens Public Library Foundation.