Sotheby's First Hip-Hop Auction Headlined by The Notorious B.I.G. & Tupac Shakur's Prized Possessions

Notorious B.I.G. photographed in New York City.
Clarence Davis/NY Daily News Archive via Getty Images

Notorious B.I.G. photographed in New York City.

Sotheby will host its first-ever hip-hop auction featuring two prized items from late hip-hop heavyweights The Notorious B.I.G. and Tupac Shakur.

While reflecting on the "Golden Age" of the genre in the mid-1980s to the mid-1990s, the auction features 120 lots and showcases iconic artifacts, contemporary and fine art, one-of-a-kind experiences, vernacular photography, vintage and modern fashion, historic and modern jewelry and luxury goods, and rare flyers and posters. Monica Lynch, the former president of Tommy Boy Records in the '90s who helped launched the careers of hip-hop legends Afrika Bambaataa & Soulsonic Force, Queen Latifah, De La Soul and Naughty by Nature among others, co-organized the auction.

The two headlining items are the crown worn and signed by Biggie Smalls from his epochal 1997 "King of New York" photo from his last-ever photoshoot and an archive of 22 handwritten love letters that Shakur penned to his high school sweetheart.

Photographer Barron Claiborne shot Biggie's regal portrait on March 6, 1997, just three days before the legendary NYC MC (real name Christopher Wallace) was fatally shot in LA on March 9, 1997. Now more than two decades later, Claiborne is giving up the crown after having it in his possession since the memorable shoot day. It bears the inscription "Crown from Biggie KONY Shot NYC 3-6-97" and is autographed by both Biggie and Claiborne. Included with the crown are three 36 x 40" prints of the iconic "K.O.N.Y" photograph that are all signed by Claiborne, the 10th-anniversary K.O.N.Y photograph, and the contact sheet. The estimated price for the Biggie lot is $200-300,000.

"After 23 years in my possession, I’m very excited to share this iconic piece of hip hop history with the public," Claiborne said in a press statement. "With the tragic events that unfolded just days after the photoshoot, this image of a crowned Notorious B.I.G. became much more than a portrait – the image transformed Biggie Smalls into an aristocratic or saint like figure, forever immortalized as not only the King of New York, but a king of hip hop music and one of the greatest artists of all time."

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On the other hand, the Shakur lot highlights his incredibly poetic handwritten love letters to Kathy Loy, who also attended Baltimore School for the Arts. The then-high school sophomore wrote them between March 1987 to April 1988, chronicling the couple's two-month-long romance and a letter of regret he sent the following year. The letters come out to a total of 42 pages on 24 sheets of paper with a singular greeting card, all signed by the West Coast hip-hop titan with numerous terms of endearment: "Love, Tupac," "4 Eternity, Tupac," "With Passion, Tupac," "Forever Yours, Tupac" and "With All My Heart, Tupac."

Enclosed in the letters are mentions of his close friend and fellow classmate Jada Pinkett Smith -- "Jada told me she can see how much I love you...," he wrote to Loy -- as well as his mother Afeni Shakur. He even confesses his doubts about pursuing his embryonic rap career as a full-time profession, writing in one letter, "My old manager came over and said she doesn't want me to retire from rap but I think I am because I can't handle too much rejection and I don't have the time...." The estimated price for the Shakur lot is $60-80,000.

"Since its birth in the Bronx in the 1970s, hip hop has become a global cultural force, whose influence has grown over the decades to shape tastes in fashion, design, art, pop culture, and much more. This auction is a celebration of that story and the many ways in which hip hop continues to resonate across all aspects of culture," said Cassandra Hatton, vp and senior specialist in Sotheby’s Books & Manuscripts Department, in the statement. "We are so pleased to announce the auction with two unquestionable pillars of hip hop — Biggie and Tupac — with lots that offer an introspective look, in their own way, beyond their respective public personas."

A portion of the Sotheby's proceeds will benefit Building Beats, a non-profit community organization based in Brooklyn that teaches entrepreneurship, leadership and life skills in New York City's low-income and minority youth through in-school and after-school DJ and music production workshops.

A dedicated exhibition will be on display by appointment at Sotheby's New York and online in a new immersive digital gallery experience from Sept. 11-15. The live auction will be held on Sept. 15.