The auction was led by the crown worn by Christopher Wallace (aka Biggie/Biggie Smalls and Notorious B.I.G.) during the 1997 ‘K.O.N.Y. (King of New York)’ portrait session, which sold for $594,750. Five bidders competed for more than 7 minutes driving the price to nearly triple the low estimate of $200,000. Recently showcased in the groundbreaking book and exhibition Contact High: A Visual History of Hip-Hop by Vikki Tobak, the crown was offered by the photographer Barron Claiborne, whose possession it has remained since the ‘K.O.N.Y’ photoshoot, which took place just three days before Biggie was killed in Los Angeles. Included in the lot are three specially sized (36 x 40") prints – all 1/1 printed and signed by Claiborne – of the iconic ‘K.O.N.Y’ photograph, the 10th anniversary K.O.N.Y. photograph, and the contact sheet. The interior of the crown bears the inscription “Crown from Biggie KONY Shot NYC 3-6-97” and is signed by both Biggie and Claiborne.

Hired by Rap Pages Magazine to photograph Biggie for the cover, Claiborne’s concept was to portray the rapper as the King of New York on his throne but in a stripped-down manner – a departure from the popular over the top Hip Hop imagery of the late 90s. To style Biggie as royal, Claiborne brought two crowns of different sizes to the shoot; one was far too small, and in order to make the now-legendary crown fit, the interior foam cushioning had to be removed. Sean "Diddy" Combs, owner of Biggie’s label Bad Boy Records, accompanied the artist on the shoot, and was reportedly unhappy with the concept, worrying that it made him look like "the Burger King". However, Biggie was open to the idea, resulting in one of the most recognizable images in Hip Hop culture and one of the most famous Hip Hop portraits ever taken.

Another standout lot was a Rammellzee vs. K-Rob “Beat Bop” original, sealed 12-inch single featuring original artwork by Jean-Michel Basquiat from 1983. Considered a “holy grail” Hip Hop record, the vinyl achieved $126,000 – exceeding its high estimate by more than 50 times. In addition to creating the graffiti-influenced cover and label artwork, Basquiat also produced, directed and independently issued the vinyl in a run of only 500 copies on his own Tartown Inc. label. The vinyl was consigned by Profile Records Co-Founder Cory Robbins, who will be donating 100% of the sale proceeds to the Archive of Contemporary Music. The sale also marks the LP as the most expensive vinyl Hip Hop record sold at auction.

Created by world-renowned Roc Nation DJ and collector of all things Hip Hop, DJ Ross One, The Wall of Boom sold for $113,400. The art installation features 32 extremely rare and vintage boomboxes from the early 1980s through the early 1990s, displayed together on a custom-built shelf, and wired together to function as a singular sound system.

A deeply personal archive of 22 autographed love letters written by a 16-year-old Tupac Shakur to Kathy Loy, a high school sweetheart and fellow student at the Baltimore School for the Arts fetched $75,600. A total of 42 pages on 24 sheets of paper and one greeting card, the letters range in date from late March 1987 to April 1988 and chronicle the approximately two-month long romance between the pair – spanning their first meeting, to their eventual break-up, and a letter of regret sent a year later. The heartfelt and sweetly sincere correspondence reveals Shakur’s vulnerability and naturally poetic writing-style, with frequent lyrical turns and separate love poems included in the body of the letters, which set the foundation for his distinctive style and tone as a rapper. Shakur writes about his nascent music career, divulging his doubts about pursuing rap as a profession, in addition to providing small glimpses into his home life with mentions of his mother working late night and his responsibilities to help care for his cousins.