Sotheby's recent Hip-Hop-themed auction achieved groundbreaking milestones with the sale of two deeply personal and significant items which belonged the late Tupac Shakur. His iconic custom made crown ring, purchased by rapper Drake, sold for $1 million. According to CBS News, the winning bid was well above Sotheby's pre-sale estimate of between $200,000-$300,000, making it the most Hip-Hop artifact ever sold according to the auction house.

In a heartwarming juxtaposition, a love letter penned by Tupac during his high school years sold for over $5,000 to Dr. Khalid El-Hakim, founder of the Black History 101 Mobile Museum. "Although the monetary value may not be as substantial as the ring, the letter's emotional worth and historical significance are immeasurable," El-Hakim told Rock The Bells.

Sotheby's held another historic auction at their first Hip-Hop-themed auction in 2020. A plastic crown owned and worn by The Notorious B.I.G. during his last photo shoot sold for $594,750. The crown which was signed by the "One More Chance" MC had an estimated presale value of between $200,000 and $300,000. According to Sotheby's, the Hip-Hop themed auctions are "dedicated to the genre's history and cultural impact."

Other lots in Sotheby's initial Hip-Hop auction include a drum kit once owned by Questlove of The Roots, one of Slick Rick's eye patches and a pair of leather jackets worn by Salt-N-Pepa in a 2015 Super Bowl commercial.