Hip hop and high art collecting has finally found common ground. Now, we can all virtually celebrate its legacy at Sotheby’s upcoming auction. 

Normally associated with classical artefacts, fine art, wine and whisky, some of the world’s preeminent auction houses have been rolling out sales reflecting the interests of the modern day buyer in street culture — whether it’s in Supreme’s highly collectible skate decks or Michael Jordan’s rarest sneakers. Now, it’s hip hop’s turn with some of the most prized pieces going under the hammer.

As Cassandra Hatton, Vice President & Senior Specialist at Sotheby’s Books & Manuscripts Department comments: “Since its birth in the Bronx in the 1970s, Hip Hop has become a global cultural force, whose massive influence continues to shape all realms of culture: music, fashion, design, art, film, social attitudes, language, and more.”

Indeed, this will be celebrated at Sotheby’s upcoming auction on 15 September in New York — the first-ever auction fully dedicated to the impact of hip hop. Up for grabs are 120 lots comprising unique artefacts, contemporary art, one of a kind experiences, photography, vintage and modern fashion, historic and newly designed jewellery and luxury items, rare ephemera including flyers and posters, important publications, and more.

The pieces headlining the auction are none other than Notorious B.I.G’s ‘King of New York’ Crown’ and a set of love letters written by a teenaged Tupac Shakur.

The crown worn and signed by Notorious B.I.G. from the iconic 1997 ‘King of New York’ photograph.

Famously worn by Christopher Wallace (AKA Biggie/Notorious B.I.G)’s during the ‘K.O.N.Y’ portrait session in 1997, the crown has been offered for auction by the photographer Barron Claiborne, who has kept it since photographing Biggie for the cover of Rap Pages Magazine — just three days before the rapper was killed in Los Angeles. Its interior bears the inscription “Crown from Biggie KONY Shot NYC 3-6-97” and is signed by both the rapper and photographer.

The idea behind Claiborne’s concept was to style Biggie as royalty, and although this was originally viewed with skepticism by label owner Sean ‘Diddy’ Combs (who reportedly worried that it made him look like the ‘Burger King’) Biggie was open to the idea. His conviction proved successful, as the photograph went on to become one of the most recognisable images in hip hop culture and one of the most famous portraits ever taken in hip hop.

Alongside the crown are also three specially sized (36 x 40 inch) prints all signed by Claiborne: one being the iconic ‘K.O.N.Y’ photograph, the other the 10th anniversary K.O.N.Y photograph, and lastly, the contact sheet. Together, the four items are estimated at US$200,000-300,000 (HK$1,550,090-2,325,135).

An archive of high school love letters handwritten by teenaged Tupac Shakur.

Next in line are Tupac Shakur’s Teenage Love Letters, written to Kathy Loy, who is the high school sweetheart of 16-year old Shakur at the Baltimore School for the Arts. With 22 in total, and written across 42 pages, the letters are a deeply personal archive written from late March 1987 to April 1988. They are all signed by Shakur in endearing terms: “Love, Tupac”, “With Passion, Tupac”, and “With all my heart, Tupac” as he chronicles the approximately 2-month long relationship with Loy, spanning their first meeting to their subsequent separation, and a letter of regret sent a year later at age 17, recalling their good times spent together, writing “Forgive me while I reminisce… do you remember?”.

Warmly heartfelt and sincere, the letters reveal Shakur’s vulnerability and naturally poetic writing style as he put his emotions into words, as seen in one instance when he wrote “I love you now more than ever, want you now more than before, No one compares to you, the one I adore…” Indeed, auctioneers can further understand his distinctive style and tone as a rapper after reading them. Other key and interesting insights that can be gained from these correspondences are Shakur’s friendship with Jada Pinkett, his home life, his nascent music career as well as his fear of rejection and lack of confidence. The letters are estimated at US$60,000-80,000 (HK$465,027-620,036).

A portion of Sotheby’s proceeds from this sale will be diverted to support the Queens Public Library Foundation in order to support their hip hop programmes, coordinated by “Uncle” Ralph McDaniels, as well as Building Beats, a non-profit community organisation that teaches tech, entrepreneurial and leadership skills to the underserved youth through DJ and music programmes. Besides being on view by appointment in Sotheby’s York Avenue Galleries from 11-15 September, the public can also access it online via the house’s new immersive digital gallery experience, slated to launch at the same time.

Explore the collection at Sotheby’s online.

This article first appeared on Lifestyle Asia Hong Kong.

Lifestyle Asia
Here's where you can read the latest news and stories from Lifestyle Asia, curated from all of our editions in Hong Kong, Singapore, Kuala Lumpur, Bangkok, India and Paris.