[UPDATE 9/16/20]: The plastic crown worn by The Notorious B.I.G. in his final photoshoot before his death—which produced the iconic “King of New York” image used as a 1997 cover photo for Rap Pages magazine—sold for $594,750 at the Sotheby‘s hip-hop auction on Tuesday night, according to the New York Post.

As photographer Barron Claiborne, who initially purchased the crown prop and shot the famous photo (as seen above), explained, “This crown is a novelty item; I bought it at a place on Broadway called Gordon’s. Without Biggie, the crown would not be worth [six figures]. I only paid six bucks for it.”

“I’m not sure that I even got paid for it,” he said. “I was mostly shooting celebrities and reportage. I did this because I liked taking pictures of Biggie. The time before, I photographed him in a white suit — instead of the tracksuit that most rappers were wearing back in 1997.”

Claiborne also noted that the photoshoot nearly didn’t happen, as he initially received pushback from Biggie’s label head, Sean “Puff Daddy” Combs: “He said it would make Biggie look like Burger King. … But Biggie didn’t listen. He wore it anyway. And nobody’s ever told me that they look at the photo and think the crown is plastic.”

Other lots included in the first-ever Sotheby’s hip-hop auction included a set of letters written by Tupac Shakur while he was in high school. The letters wound up selling for more than $75,000.

You can browse all the sale results from the auction here.

[9/25/20]: Famed auction house Sotheby’s is dipping its toes into the hip-hop world with a special auction of high-value memorabilia from Tupac ShakurThe Notorious B.I.G., and more.

“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, via press release. “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.”

The auction features 120 lots including iconic hip-hop artifacts, contemporary and fine art, vintage and modern fashion, jewelry, and luxury goods, and rare posters and flyers from the genre’s mid-’80s–mid-’90s “Golden Age.” The auction was co-organized by Monica Lynch, the former president of Tommy Boy Records, which helped launch the careers of a generation of hip-hop acts like De La SoulQueen LatifahAfrika Bambaataa, and Naughty By Nature.

Related: Watch A 17-Year-Old Biggie Smalls Spit Fire On A Brooklyn Street Corner [Video]

The marquee items up for auction include the crown worn and signed by The Notorious B.I.G. from his iconic “King of New York” photoshoot with photographer Barron Claiborne in 1997, his final photo session before he was gunned down in Los Angeles just three days later. The crown, which has been in Claiborne’s possession since the shoot, bears the inscription “Crown from Biggie KONY Shot NYC 3-6-97″ and is autographed by both Biggie and Claiborne. Included with the crown’s lot are three 36″ x 40” prints of the famous photo, the 10th-anniversary “K.O.N.Y.” photo, and the contact sheet. As Billboard notes, the Biggie lot is expected to sell for anywhere between $200K and $300K.

“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 release. “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.”

Related: Third Man Records To Auction Used Instruments, White Stripes Memorabilia, Rare Studio Gear, More

The Tupac Shakur lot at the Sotheby’s hip-hop auction is not as directly tied to the foundational West Coast M.C.’s career. Rather, it pulls from his pre-fame days in the form of love letters written to former flame Kathy Loy when he was a sophomore at Baltimore School for the Arts. Notes Billboard, “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.'” Tupac’s Sotheby’s lot is expected to fetch anywhere from $60K to $80K at auction.

Of note, the letters also make reference to Shakur’s longtime friend, actress Jada Pinkett Smith (“Jada told me she can see how much I love you”). In the letters, he expresses doubts about pursuing a career in music. As Tupac writes in the letters, “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 refection and I don’t have the time…”

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.