24 Iconic Pop Culture Items That Sold for a Ton of Money
While society tends to put celebrities on a pedestal, they aren’t above offloading merchandise to pay hefty tax bills or support ne’er-do-well offspring. Use these stars (and fortunate recipients of celebrity keepsakes) as inspiration for your own garage sale, if you wish.
Many of the items on this list belonged to some of the most beloved celebrities of their era, including Elizabeth Taylor and Jerry Garcia. If you have disposable income, you might consider whether investing in unique celebrity merchandise could prove a lucrative strategy. As you will soon see, the allure of popular culture can be a potent investment vehicle.
While you might list your little-used personal items on Craigslist or OfferUp after reading, the rich and famous turn to auctioneers like Sotheby’s to peddle their wares. A select few celebrities and those fortunate to own their trinkets found that their seemingly run-of-the-mill items commanded a modest fortune in the public marketplace.
1. Kurt Cobain’s MTV Unplugged Guitar: $6 Million
MTV Unplugged stripped back the polished production tricks from artists, making for some of the most intimate, soulful concerts of their era. Nirvana’s concert is particularly iconic, as it was recorded in November 1993, only months before Cobain’s unexpected death in April 1994.
The acoustic-electric 1959 Martin D-18E Cobain used in the unscripted, raw performance holds a special place in fans’ hearts. Rode Microphones founder Peter Freedman bought the instrument at a 2020 auction for about $6 million.
2. Elizabeth Taylor’s La Peregrina Pearl Necklace: $11.8 Million
Elizabeth Taylor served as the gold standard for elegance in mid-20th century American culture, and her jewelry serves as the gold standard of celebrity memorabilia. Items like her La Peregrina Pearl necklace have inherent value, but the fact that the necklace belonged to Taylor explains the accessory’s $11.8 million sale price.
The piece includes over 50 pearls, multiple rubies, and other valuable stones. Its ownership also traces back to European royalty, which is why it was one of Taylor’s most prized possessions.
3. Marilyn Monroe’s JFK Dress: $4.8 Million
The term “generational beauty” is thrown around far too often. Only as generations come and go can you truly brand someone as a once-in-a-generation icon, and Marilyn Monroe has passed that test.
The blonde bombshell’s cultural impact seems to grow with each decade. In 2016, her bedazzled dress, which Monroe wore as she serenaded President John F. Kennedy during his 45th birthday party, sold for $4.8 million. This makes it a compelling (and expensive) historical garment.
4. Audrey Hepburn’s My Fair Lady Dress: $4.5 Million
When it comes to high-value celebrity memorabilia, names like Taylor, Monroe, and Hepburn are among the most bankable. Died-in-the-wool Hepburn fans rank Hepburn next to Mother Teresa in terms of idols, and not necessarily in that order. This rare degree of fandom helps explain why Hepburn’s iconic dress from My Fair Lady fetched $4.5 million in 2011.
The fact that My Fair Lady won eight Oscars, including for Best Costume Design, only enhances this high-priced item’s value.
5. Jerry Garcia’s “Wolf” Guitar: $3.2 Million
When someone says, “cult following,” there is no greater example than The Grateful Dead fanbase. These fans are loyal enough to travel worldwide, attending one Dead concert after the next.
It should be no shock that Jerry Garcia’s favorite guitar, Wolf, commanded a sale price of $3.2 million (to go to charity) in 2017.
6. Michael Jordan’s Game-Worn Shoes: $2.24 Million
His Airness is synonymous with shoes. When someone says “Jordans,” most know they’re referring to the revered line of athletic sneakers. When someone says, “Air Jordan XIIIs worn in Game 2 of the 1998 NBA Finals,” they’re referring to the autographed pair that sold for $2.24 million in 2023.
While Jordan was not the seller, he has made a habit of giving away shoes that go on to sell for eye-popping sums, making him a kingmaker.
7. John Lennon’s “Imagine” Piano: $2.1 Million
Who is better suited to appreciate the historical significance of John Lennon’s “Imagine” piano than a fellow musician? George Michael reportedly outbid fellow Brit musicians Robbie Williams and the Oasis duo Noel and Liam Gallagher to acquire the iconic instrument at a 2000 auction.
Imagine paying $2.1 million for the piano used to compose a song with the line “Imagine no possessions.” Now, that is rich.
8. Bob Dylan’s Handwritten “Like a Rolling Stone” Lyrics: $2.045 Million
Bob Dylan is a musician you can’t put in a box. He went acoustic, electric, and even religious throughout his prolific musical career, and “Like a Rolling Stone” remains one of his most replay-worthy hits. Dylan fans are diehard by nature, as evidenced by the 2014 purchase of the handwritten “Like a Rolling Stone” lyrics for $2.045 million.
The lyrics, written on hotel stationary, even include lines that did not make the song’s final cut. As far as Dylan’s memorabilia goes, this is as unique as it gets.
9. Elizabeth Taylor’s Taj Mahal Diamond: $8.8 Million
Elizabeth Taylor lived a high-flying life with iconic stories, luxury goods, and timeless memorabilia. A Taj Mahal diamond gifted to Taylor by Richard Burton for her 40th birthday is one of the most coveted of all Taylor-centric merch.
The diamond has been the focus of a legal battle since its 2011 sale for $8.8 million. Whether the diamond was owned by the Emperor who commissioned the construction of the Taj Mahal is one of several points of contention between the Taylor estate and Christie’s auction house.
10. Judy Garland’s Ruby Slippers: $2 Million
Some films are so monumental that memorabilia associated with the movie has a guaranteed market. The Wizard of Oz tops the list of such attention-commanding movies, and the ruby slippers are arguably the most important memorabilia from the era-defining movie.
A group representing the Academy of Motion Picture Arts and Sciences purchased one of the few ruby slippers Judy Garland (aka Dorothy) worn for $2 million in 2012.
11. Michael Jackson’s Autographed Thriller Jacket: $1.8 Million
No music video looms larger in popular culture than “Thriller.” The video felt like a mini-movie, and Michael Jackson’s red leather jacket is seared in the memories of pop-loving fans for eternity.
Two years after Jackson’s passing, in 2011, one King of Pop fan from Texas purchased the iconic outfit for $1.8 million with plans to raise money for children’s healthcare. Last we heard, the jacket was displayed at Dell Children’s Hospital in Austin, TX.
12. Judy Garland’s Dress from The Wizard of Oz: $1.565 Million
Judy Garland’s iconic blue and white gingham pinafore dress is not in Kansas anymore. As of 2015, the dress is in the possession of a wealthy, successful bidder who paid $1.565 million for the timeless piece of Hollywood memorabilia.
Ding, dong, the auction is over. Perhaps the next auction will be yours, as that Wizard of Oz DVD you never watched might be ripe for an eBay listing.
13. Marilyn Monroe’s Seven Year Itch Dress: $4.6 Million
Marilyn Monroe’s initials (MM) are, perhaps not coincidentally, also shorthand for “millions.” You won’t get your hands on any significant Monroe memorabilia without shelling out millions, and her dress from the movie The Seven Year Itch is no exception.
You don’t own the dress, but you know it. It is the white billowing garment Monroe held down as a breeze from a subway grate gusted upward. Actress Debbie Reynolds owned the dress when it sold for $4.6 million in 2011.
14. Julie Andrews’ Sound of Music Dress: $1.56 Million
The Sound of Music remains near the top of most “Best Movies of All Time” rankings, as few musicals blend frolicking in fields and Axis invasion so seamlessly. When outfits from the movie hit the auction block in 2013, high demand was a certainty.
Yet, even the most optimistic auctioneers could not have predicted that Julie Andrews’ iconic “Do-Re-Mi” dress and certain other clothing from the film would fetch $1.56 million. The Sound of Music is eerily similar to the sound of money.
15. Producer David O. Selznick’s Gone with the Wind Oscar: $1.54 Million
Not every Oscar trophy holds the same value, and producer David O. Selznick’s Oscar for Gone with the Wind is the cream of the crop. The film won Best Picture in 1939 and remains one of the most revered, before-its-time movies in the Hollywood pantheon. Selznick is an accomplished producer who worked on A Star Is Born, King Kong, and other iconic films.
Michael Jackson purchased the trophy for $1.54 million in 1999, further enhancing the lore of the valuable keepsake.
16. David Prowse’s Darth Vader Helmet: $1 Million
Darth Vader once menacingly boasted to Lando Calrissian, “I am altering the deal, pray I don’t alter it any further.” Fortunately for one diehard Star Wars fan, the auctioneer overseeing bidding at a 2019 auction honored the terms of the deal. Those terms were $1 million in exchange for the Darth Vader helmet actor David Prowse wore in Star Wars: Episode V: The Empire Strikes Back.
Rare Star Wars merchandise will always find a financially-endowed fanboy (or fangirl) willing to pay a modest fortune. Consider this fact as you build your investment portfolio.
17. Audrey Hepburn’s Breakfast at Tiffany’s Dress: $807,000
Breakfast at Tiffany’s has been called a film that “will never go out of style,” and Audrey Hepburn’s fashion choices play no small role in the film’s interminable cool.
The black Givenchy dress Hepburn’s Holly Golightly wore in the movie prompted several fans to bid high. The dress sold for $807,000 in 2006, with proceeds going to assist the plight of India’s significantly impoverished population.
18. J.K. Rowling’s Writing Chair: $394,000
The Harry Potter franchise has proven a veritable cash cow imported from the United Kingdom. Author J.K. Rowling has become a billionaire selling film rights, securing endless merchandising opportunities, and even approving the creation of a Wizarding World in Orlando, FL.
Yet, the sale of J.K. Rowling’s oak chair (in which she reportedly wrote the first two Potter novels) for $394,000 may be her most impressive act of magic yet.
19. Mahatma Gandhi’s Gold-Plated Glasses: $340,000
Mahatma Gandhi once said, “An ounce of patience is worth more than a ton of preaching.” If he were alive, Gandhi might be shocked to learn that one pair of his gold-plated spectacles is worth $340,000.
The pair sold for more than 17 times its estimated value in 2020. Now, the buyer can see the world as Gandhi did. Hopefully, the hefty purchase price will come with a heaping helping of enlightenment.
20. Kurt Cobain’s Cardigan Sweater: $334,000
Kurt Cobain’s short but impactful run as Nirvana frontman has made him a cash cow even in the afterlife. Cobain remains a potent brand among music and pop-culture aficionados, from college dormitory posters to remastered records. If you’re not convinced of this, consider that a stained, cigarette-singed cardigan Cobain wore during a 1993 MTV Unplugged performance fetched $334,000 in 2019.
When someone tells the sweater owner to “come as you are” to the Christmas party, they’d be a fool not to wear the $334,000 sweater as an unrivaled conversation piece.
21. John Lennon’s Sunglasses: $183,000
Imagine all the people…who bid on John Lennon’s sunglasses to pump the bidding to $183,000. Former Lennon chauffeur Alan Herring tasked Sotheby’s with selling the shades in 2019, and the final sale price far outpaced the expected value of between $8,000 and $10,600.
The story goes that Lennon was only wearing the glasses for the look, so he thought nothing of leaving them to Herring after Lennon forgot the sunglasses in his chauffeur’s vehicle.
22. Elvis Presley’s Hair: $115,120
In almost every circumstance, keeping a vial of someone else’s hair is creepy. There are a few exceptions, like when a spouse has gone to war, passed away, or gifted the hair in some sentimental way. The other glaring exception is when the hair belongs to The King of Rock and Roll, Elvis Presley.
In 2002, the ultimate Elvis buff paid $115,120 for a jar of the king’s hair, which has frizzed considerably over the years. Collected from Elvis’ haircuts, the jar is the “largest and most well-documented collection of Elvis’ hair in the world,” as if there is a robust market for Elvis’ hair.
23. One Direction’s Niall Horan’s Half-Eaten Toast: $100,000
You might not recognize the name Niall Horan if you were born in 1992 or earlier. He’s one of the members of One Direction, an unfathomably popular pop band with a dedicated horde of followers that make Beatles fans look sedated by comparison.
An Australian broadcaster listed a half-eaten toast on eBay after One Direction visited the studio and sampled the breakfast platter. A bidder forked over $100,000 for the gnawed-on bread, making it the most expensive piece of toast in the history of sliced bread.
24. Michael Jackson’s Party Jacket: $65,625
Kim Kardashian purchased a party-worn jacket formerly owned by Michael Jackson for $65,625 in a classic case of taking from the rich to give to the rich. The 2019 purchase reportedly went straight to Kim’s daughter North West.
If there is anyone who can appreciate the historical significance of Michael Jackson’s bedazzled jacket, it’s a child.
