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The Original iPhone, iPod Touch, and iPhone 3G on a glass table with magazines underneath
The Original iPhone, iPod Touch, and iPhone 3G on a Glass Table by Masaaki Komori (CC BY-SA)

It’s not hard to understand why items of historical value go for astronomical sums at auction, but then there’s the occasional oddity that sells for more than anyone would imagine. Case in point: An unopened first-generation iPhone from 2007 is sold at auction for $63,000 — considerably more than the initial $599 price tag. Whether run-of-the-mill or extraordinary, an object’s value often bears little resemblance to its practicality, as suggested by the record amounts spent at recent auctions of items in various categories.

Related: The Most Expensive Clothing Items Ever Sold at Auction

The Hourglass From ‘The Wizard of Oz’

Judy Garland (right) as Dorothy and Margaret Hamilton as the Wicked Witch of the West in the musical film 'The Wizard of Oz', 1939.
Silver Screen Collection/Getty

Price: $495,000Year: 2022

Dubbed “the most recognizable signature prop from the film” by the auction house that sold it, the hourglass ticked off the moments the Wicked Witch of the West said Dorothy had left to live, cackling, “You see that? That’s how much longer you’ve got to be alive! And it isn’t long, my pretty! It isn’t long! I can’t wait forever to get those shoes!” Don’t get any ideas about using the wood-and-paper maché prop as a real timer, though. The glass is filled with red glitter for display, but it doesn’t flow through the hourglass’ narrow neck. Related: Iconic Movie Props That Went Missing

Mark Zuckerberg Baseball Card

Mark Zuckerberg Little League Baseball Card
ComicConnect

Price: $105,000

Year: 2022

Though baseball cards from acclaimed athletes such as Mickey Mantel and Babe Ruth have been known to sell for millions of dollars, a baseball card from Mark Zuckerberg’s Little League days just fetched an impressive $105,000 at an auction hosted by Comic Connect. After including a buyer’s premium, the total came to $120,750. The card, which was signed by Zuckerberg and features the Meta CEO at age 8, also sold as a non-fungible token, or NFT, for 11 ethereum (about $14,800) in a simultaneous digital auction. Ethereum is a form of cryptocurrency.

Related: Sports Collectibles That Scored Big at Auction

Adolf Hitler’s Watch

German Fuhrer and Nazi leader Adolf Hitler watches soldiers with his back facing the camera at a Nazi rally in Dortmund, Germany.
Hulton Archive/Getty

Price: $1.1 million

Year: 2022

In a more controversial auction at a Maryland-based auction house, a wristwatch that belonged to Adolf Hitler, complete with his initials and a swastika, sold for $1.1 million — despite being valued at $2 million to $4 million and labeled as a “World War II relic of historic proportions,” by Alexander Historical Auctions in Chesapeake City. But Jewish leaders and community members disagreed, saying the watch had no historical value and they even referred to the auction as “abhorrent” in an open letter signed by 34 individuals in an attempt to have the watch removed from auction. For his part, the president of the auction house, Bill Panagopulos, defended the sale since the buyer was a European Jew.

Buzz Aldrin’s Apollo 11 Moon Jacket

Alexi Rosenfeld/Getty Images

Price: $2,772,500

Sold: 2022

The jacket Buzz Aldrin wore on his historic first mission to the moon in 1969 recently sold for nearly $2.8 million in an auction at Sotheby’s. The winning bidder made the sale in a short 10-minute bidding war. The jacket has Aldrin’s name tag above the Apollo 11 mission emblem and is made of unique fire-resistant material.

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2 Japanese Melons

Japanese Melon
Yubari Melon by Captain76 ((CC BY))

Price: $29,251 Sold: 2018

The president of a fruit and vegetable packaging company paid this amount for just two melons grown in Yubari, Japan. It easily beat the previous record ($27,423.28) set in 2016, and more than doubled the amount ($13,711.64) paid for a similar pair last year. Shinya Noda, the president of Hokuyu Pack, wanted to set a record to celebrate his company’s 30th anniversary and planned to cut the melons into pieces and give them to customers.

Related: Foods That Sold for Big Money at Auction

Leica 0-Series No. 122 Camera

Leica No.122 Camera
LHSA.org

Price: $2.97 million Sold: 2018

This is a 1923 prototype produced before this German-made line of upscale cameras went to market, and it’s pricey whenever it goes on sale. Another version sold for $2.6 million back in 2012, but this one hit the block with a starting price of just $492,000. A private collector in Asia made the final phone bid for this camera, which was in original condition.

A Bunch of Grapes

Ruby Roman Grapes
Ebay

Price: $11,000 Sold: 2016

This price is for a bunch, mind you: 30 grapes, at $360 apiece. Ruby Roman grapes were developed during 14 years and bred for minimal acidity and maximum sweetness. The supermarket owner who bought them gave customers a taste of his prize; in a previous grape auction in 2011, the purchasing chef threw them right into a dessert.

1943 Patek Philippe Watch

1943 Patek Philippe Watch, Ref. 1518
Phillips

Price: $11,136,642Sold: 2016

A 13-minute bidding war pushed the price for this steel-cased, perpetual-calendar chronograph into eight digits. Since it’s one of only four in existence, you’ll forgive the bidders their urgency.

Lunch With Warren Buffett

Warren Buffett
Warren Buffett by USA International Trade Administration ((CC BY))

Price: $3.5 million Sold: 2016

For more than a decade, Berkshire Hathaway billionaire Warren Buffett has auctioned off a lunch at a Smith & Wollensky steakhouse in New York to raise money for the Glide Foundation, which helps the homeless in San Francisco. In 2016, however, an anonymous donor won the eBay auction with this numerically sequenced bid. Gaming companies and hedge fund managers have paid more than $2 million for this lunch in previous years, but this bidder did without the publicity.

M4 Enigma Coding Machine From World War II

German Enigma Machine
Giorez/istockphoto

Price: $365,000Sold: 2015

Germany’s formerly uncrackable coding device from World War II resurfaces occasionally around the globe, but only about 150 of the 1,500 built still exist. Built with four rotors instead of three to thwart Allied codebreakers at the end of the war, the M4 was cracked by mid-1943 and both German and Allied forces destroyed the machines toward the end of the war to preserve state secrets.

Indian Prime Minister Narendra Modi’s Suit

Narendra Modi
PM Modi by Narendra Modi ((CC BY-SA))

Price: $691,890 Sold: 2015

A diamond merchant bought the Prime Minister’s suit, which was embroidered with Modi’s name in gold, with the proceeds supposedly going to cleaning India’s holy river, the Ganges. Modi wore the suit during one of former president Barack Obama’s trips to India.

1856 1-Cent Magenta Stamp From British Guiana

One-Cent Magenta Stamp
Sotheby’s

Price: $9.5 million Sold: 2014

This item is the only known example of the rarest of stamps, and it sold for nearly 1 billion times its face value. Printed on a newspaper press brought over explicitly for its creation and rediscovered by a 12-year-old Scottish boy living in South America in 1873, it has set records each time it’s changed hands since 1900. In 1932, it sold for $32,500. In 1970, $280,000. During its previous sale in 1980, it fetched $935,000.

Romanée-Conti Wine

Romanee-Conti Wine
Sotheby’s

Price: $1.6 million Sold: 2014

This 114-bottle superlot was already a big deal when it went up for bid in October 2014. But with a final price reaching $1,700 a glass for 912 glasses, this wine should probably should be reserved for the most special occasions.

The Macallan Imperiale M Whisky

Macallan Decanter
Sotheby’s

Price: $628,205 Sold: 2014

Forty of these 28-inch tall, 6-liter decanters were created, but only four survived the process. Named after the Roman emperor Constantine, it took 17 craftsmen more than 50 hours to complete. The rare whisky inside comes from seven casks dating back 25 to 75 years. 

Flowing Hair Silver Dollar Coin

Flowing Hair Silver Dollar
Flowing Hair Silver Dollar by National Numismatic Collection, National Museum of American History ((CC BY))

Price: $10 million Sold: 2013

Why $10 million for just one coin? Well, considering that it was struck in 1794, it is believed to be the first from the U.S. Mint in Philadelphia. Though it was sold several times before, this version depicting Lady Liberty on one side and an eagle on the other is in incredible condition and has historic value far outweighing its features.

Vostok Space Capsule

Vostok Space Capsule
Sotheby’s

Price: $2.88 million Sold: 2011

This spherical space capsule was flown with a cosmonaut mannequin named Ivan Ivanovich in March 1961, just 18 days before Yuri Gagarin’s first space flight. An exact twin of Gagarin’s Vostok 3KA-3 capsule, this ship not only paved the way for Gagarin, but was used by other cosmonauts in training exercises. It served as the model for Russian spy satellites but, after this sale, became the only Vostok spaceship outside of Russia and the only one that is privately owned.

John Lennon’s Tooth

John Lennon
John Lennon by Nationaal Archief

Price: $36,857 Sold: 2011

It’s already weird that Dr. Michael Zuk, a Canadian dentist, spent this much on a molar reportedly belonging to John Lennon. That the molar has its own website hawking tooth-related merchandise is even more bizarre. But the assertion that the tooth can be used to clone John Lennon himself is likely where this molar’s brief run of fame should end.

Pink Diamond Barbie

Pink Diamond Barbie
If It’s Hip, It’s Here

Price: $302,500 Sold: 2010

Designed by Australian jeweler Stefano Canturi, this version of the classic doll wears a black evening dress and a 1 carat pink diamond necklace with 3 carats of white diamonds around it. Proceeds from the auction went to breast cancer research.

‘Do I Love You (Indeed I Do)’ 7-Inch Vinyl Record

Frank Wilson Vinyl
The Men Of Motown Records/facebook.com

Price: $33,861 Sold: 2009

Motown singer Frank Wilson released one single, in 1965, and only 250 copies were ever pressed — with most destroyed when Wilson decided to switch to writing and producing. The song, however, became a huge hit in the U.K. when the 7-inch vinyl record was stumbled across in the late 1970s. The seller, Kenny Burrell, meanwhile, says he parted with it only to enhance his credibility as a record expert.

Baseball Autographed by Joe DiMaggio … and Marilyn Monroe

Joe DiMaggio and Marilyn Monroe Baseball
Etsy

Price: $191,200 Sold: 2006

The iconic actress married and divorced New York Yankees Hall of Fame center fielder Joe DiMaggio in 1954, but by the time they reconnected at the Yankees’ spring training in Florida in 1961, they were trying to reconcile. That’s where this ball from the estate of late Associated Press photographer Harry Harris was signed, and that’s what makes it one of the rarest discoveries in baseball memorabilia

666-6666 Phone Number

iPhone
CatLane/istockphoto

Price: $2,746,498Sold: 2006

The foreboding phone number sold for 10 million Qatari riyals ($2,746,498) in a charity auction in Qatar. The auction started with eight interested buyers and quickly narrowed to two competitors, who fought it out until the bitter end.

Hand-Cut Jigsaw Puzzle

Hand-Cut Jigsaw Puzzle
Ebay

Price: $27,000 Sold: 2005

Rachel Page Elliott hand-cut this wooden puzzle to benefit the The Golden Retriever Foundation and sold it during a charity event at the Eisenhower Conference Center in Gettysburg, Pennsylvania. The author of a book and video on canine anatomical structure and movement, Elliott created a work consisting of 467 interlocking pieces, with many cut in her unique designs of birds, cats, horses, and golden retrievers.

Virgin Mary Grilled Cheese

Grilled cheese
AimeeLeeStudios/istockphoto

Price: $28,000 Sold: 2004

Floridian Diane Duyser made a sandwich but couldn’t eat it when she saw an image of the Virgin Mary in the bread — so she held onto it for 10 years, untouched. An online casino bought and resold it, with at least part of the proceeds going to charity. How does a grilled cheese not get moldy in that time? Well, according to Slate, if you keep moisture out, use fatty margarine to cook it, and use high-calcium American cheese to boost acid content, a grilled cheese can remain unspoiled for years.

Keith Moon’s Drum Kit

Keith Moon Drumset
Christie’s

Price: $252,487 Sold: 2004

This five-piece 1968 Premier drum kit was used by The Who’s Keith Moon until 1970. With The Who logo on it in orange and black, the kit was used at The Rolling Stones’ Rock N Roll Circus, The Who’s U.S. tour, Woodstock, the Isle Of Wight Festival, and the concert at Leeds University that led to the “Live At Leeds” album. A private U.S. bidder paid nine times the presale estimate of $26,740.

A Kiss From Sharon Stone

Sharon Stone
Sharon Stone by Gage Skidmore ((CC BY-SA))

Price: $50,000 Sold: 2003

Fan Joni Rimm paid for a 45-second kiss with the “Basic Instinct” actress 15 years ago as part of a charity initiative. The proceeds went to Project Angel Foods — a Los Angeles based charity providing free meals for people with HIV and AIDS.

World’s Oldest Postcard

Vintage postcard
1970s/istockphoto

Price: $41,758 Sold: 2002

This correspondence may also be the most expensive practical joke ever sold at auction. The card was sent in 1840 to Theodore Hook in Fulham, an English playwright and novelist noted for his wit and drollery. Hook sent it to himself as a joke, but its discovery in 2001 was historic: Before then, it was believed that the postcard was invented in Austria, Germany, or the United States some two decades later.

117-Year-Old Cadbury Chocolate Bar

Cadbury Chocolate Bar
Rinelle/istockphoto

Price: $687 Sold: 2001

Though not as expensive as some of this other items on this list, it’s not less valuable. This more than 100-year-old Cadbury’s chocolate bar accompanied Capt. Robert Scott’s first expedition to the Antarctic from 1901 through 1904. The 4-inch bar, wrapped and uneaten in a cigarette tin, was part of 3,306 pounds of cocoa and chocolate Scott took on the trip.

Dr. Alexander Macklin’s Diary

Alexander Macklin and crew sailing to Antarctica
Royal Geographic Society

Price: $153,573 Sold: 2001

His isn’t the biggest name in history, but it’s one of the more significant. Macklin served as a surgeon to Sir Ernest Shackleton during his exploration of Antarctica from 1914 to 1917. The diary and archive that Macklin compiled were deemed so historically important that the U.K.’s National Heritage Memorial Fund paid the cost.

Dorothy’s Ruby Slippers

Dorothy’s Ruby Slippers, 1938 by David ((CC BY))

Price: $660,000 Sold: 2000

The Smithsonian says there are five pairs of ruby slippers from the 1939 movie “The Wizard of Oz” kicking around, but they have a habit of disappearing. The first pair wasn’t offered for sale until 1970 and went for $15,000.

Meet the Writer

Jason Notte is a personal finance reporter for TheStreet. His work has appeared in several outlets including The Newark Star-Ledger, The New York Times, The Huffington Post and The Boston Globe. He previously served as the political and global affairs editor for Metro U.S. and the layout editor for Boston Now, among other roles at various publications. Notte earned a Bachelor of Science in Journalism from the S.I. Newhouse School of Public Communications at Syracuse University in 1998