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The Most Expensive Things Ever Bought at Auction, Ranked by Regret

A banana, a dinosaur and a stamp that lost a million dollars. Ranked from no regrets at all to he ate it.

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Maurizio Cattelan, Comedian, Sotheby's, 2024
Photo via NBC News

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Auctions are where very rich people go to make decisions in public, quickly, while a man with a gavel says “fair warning.”

We looked at some of the most spectacular sales of the last few years and ranked them by a scientific measure we invented: how the buyer must feel now. We start with no regrets and work our way to the fruit.

The Rankings

6. The Stegosaurus

"Apex" Stegosaurus skeleton, Sotheby's, 2024 $44.6 million

Apex Stegosaurus skeleton, Sotheby's, 2024
Photo via NBC News

Estimated at about $6 million, it sold for $44.6 million after a 15-minute bidding war won by Citadel founder Ken Griffin. It is about 150 million years old, nearly 27 feet long and has 254 bones. Griffin said Apex would stay in America.

Necessity: 0%

Verdict: Zero regrets. He bought a dinosaur. Have you ever bought a dinosaur?

5. The Ruby Slippers

Dorothy's slippers, The Wizard of Oz, Heritage Auctions, 2024 $32.5 million

Dorothy's slippers, The Wizard of Oz, Heritage Auctions, 2024
Photo via NPR / WLRN

Stolen from a museum in 2005 and recovered by the FBI in 2018, the slippers sold for more than 10 times their estimate. The thief reportedly got rid of them after learning the rubies were glass. The buyer paid $32.5 million knowing exactly that.

Necessity: 0%

Verdict: There's no place like home, and no price like this.

4. The Original Birkin

Jane Birkin's own Hermès Birkin, Sotheby's Paris, 2025 About $10.1 million

Jane Birkin's own Hermès Birkin, Sotheby's Paris, 2025
Photo via NBC Washington

The very first Birkin, with her initials under the lock, a strap that never comes off and a nail clipper still attached. It became the most expensive handbag ever sold at auction, beating the old record by roughly $9.6 million.

Necessity: 0%

Verdict: The nail clipper alone is worth about $10 million.

3. The Whisky

The Macallan 1926, Adami label, Sotheby's London, 2023 $2.7 million

The Macallan 1926, Adami label, Sotheby's London, 2023
Photo via NBC DFW

Sixty years in a sherry cask, one of only 12 bottles with a label painted by artist Valerio Adami, and the most expensive bottle of whisky ever sold. The cruel twist is that opening it would destroy most of its value.

Necessity: 0%

Verdict: The world's most expensive drink you can never drink.

2. The Stamp

British Guiana 1c Magenta, Sotheby's, 2021 $8.3 million

British Guiana 1c Magenta, Sotheby's, 2021
Image via Wikimedia Commons

Ounce for ounce, possibly the most valuable object on Earth. It sold for $8.3 million in 2021, which sounds great until you learn it sold for $9.48 million in 2014. The buyer later split it into about 80,000 shares. Nobody can mail anything with it.

Necessity: 0%

Verdict: Lost a million dollars on a one-cent stamp. Return to sender.

1. The Banana

Maurizio Cattelan, Comedian, Sotheby's, 2024 $6.2 million

Maurizio Cattelan, Comedian, Sotheby's, 2024
Photo via NBC News

A banana duct-taped to a wall sold to crypto founder Justin Sun for $6.2 million. The banana was not technically included, only the certificate and instructions, because fruit rots. Nine days later he ate the banana at a press conference.

Necessity: 0%

Verdict: He ate it. Necessity: 0%. Potassium: 12%.

The Bottom Line

The lesson, as always: buy the dinosaur, never eat the art.

Prices and details as reported by the sources linked here, and subject to change. Photos courtesy of the sources linked. Sources: NBC News on Apex · NPR via WLRN · NBC Washington · NBC DFW · Wikipedia · NBC News on Comedian


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