When an enterprising young man named James Christie opened his sales rooms in London in December 1766, his first auction consisted of the estate of a “deceased nobleman” containing “a large Quantity of Madeira and high Flavour’d Claret.” The records don’t relate how much these delightfully described “high Flavour’d clarets” fetched but as the whole sale realized a grand total £175, it is a sure bet that if Christie had known that two hundred years later, in 1985, his now famous auction house would sell one bottle of wine for £105,000, or $160,000, he might have held back a bottle or two to enrich his future heirs.

This bottle was a Bordeaux, a 1787 Chateau Lafite, and, according to The Guinness Book of World Records, 18 years later it still is the world’s most expensive bottle of wine. Its great age alone would have ensured a good price but what gave it its special cachet, especially to American collectors, and ensured the record price tag were the initials Th.J. etched in the glass.

The bottle had belonged to Thomas Jefferson, the third president of the United States and one of the most revered of its founding fathers. A philosopher, scientist and statesmen, the aristocratic Jefferson was also an avid oenophile. When he was ambassador to France he spent much of his time visiting the vineyards of Bordeaux and Burgundy, buying wine for his own collection and on behalf of his friends back home. He is also associated with two other bottles of very pricy wine, a 1775 Sherry ($43,500) and the most expensive white wine ever sold, a 1787 Chateau d’Yquem ($56,588).

Of course none of these wines are actually drinkable now; it is unusual for even the best Bordeaux to last more than 50 years, and 200 years is beyond any wine’s limit. The allure of these high-priced bottles of vinegar, and other wines of its ilk, is purely in the joy of collecting, not consuming. The 1787 Lafite was explicitly bought as a piece of Jefferson memorabilia, not as a bottle of wine, and it now resides in the Forbes Collection in New York. These wines are rather like old stamps, something to be collected, horded but never used, and they command such high prices not because of their utility but because of their scarcity and consequent appeal to collectors.

Compiling a list of the World’s Most Expensive Bottles of Wine is not as simple as it might first appear. How do you compare the price paid for a double magnum–that’s four bottles–to a single bottle? Do you rate them on the same scale or do you divide the price of the big bottle by four in order to determine its per-single bottle price?

So, rather than compiling a league table we determined 11 separate categories, then sought out the most expensive bottle in each category, and a pretty interesting search it turned out to be. One of the first things you’ll notice is that all the wines on the list were sold at auction, because, except in rare occasions, the seller knows that the publicity surrounding a special bottle, and the heated atmosphere of competitive bidding, often results in even higher prices.

The world’s most expensive bottle of wine that could actually be drunk today is also the most expensive wine ever sold in America, a Montrachet 1978 from Domaine de la Romanée-Conti that was hammered down at Sotheby’s (nyse: BID – news – people ) in New York in 2001. The lot of seven bottles fetched $167,500, or $23,929 per bottle. This is an extraordinary price for a white wine, even in the rarified world of wine collecting. What happened was that two avid collectors were bidding against each other and got carried away, each refusing to yield as the price rose through the stratosphere.

Michael Broadbent, the former head of Christie’s wine department, relates a similar story concerning the sale of the Jefferson Lafite. As the bidding approached £100,000 for this unique bottle, he changed bid steps, that is the amount the bids increased by. One of the two remaining bidders was Marvin Shanken, publisher of the Wine Spectator, and according to Broadbent, he didn’t notice the change until, to his very obvious horror, he realized that he had just offered to pay £100,000 for one bottle of wine. As he sat there ashen faced a great hush fell over the packed auction room as everyone waited to see if the other bidder, Christopher Forbes, would come back in. He eventually did, at £105,000, much to Shanken’s very palpable relief.

Then there is the strange case of the most expensive bottle of wine never sold. In 1989 William Sokolin, a New York wine merchant, had a bottle of Chateau Margaux 1787, also with Jefferson’s initials, on consignment from its English owner. He was asking $500,000 for it but had had no cash offers when he took it along to a Chateau Margaux dinner at the Four Seasons restaurant. (Why would it cost so much more than the 1787 Lafite? It didn’t cost more than the Lafite, just that Sokolin was asking $500,000. I don’t think he expected to get this much and had had no offers by the time of the accident. However, just by asking such a huge sum he generated a lot of publicity, which some people speculate was the whole point of the exercise. He did however get $225,000 from the insurance company which he claims, with some justification, makes it the world’s most expensive bottle, even if it was never sold. Besides everything else it’s a fun story about a very expensive bottle however you rate it.)

At the end of the evening he was getting ready to leave when a waiter carrying a coffee tray bumped the bottle, breaking it. Luckily, Sokolin had the foresight to insure his valuable vin, and shared the $225,000 payout with the owner, which makes this the world’s most expensive broken bottle of wine. History does not tell us what happened to the unfortunate waiter.

What all these wines have in common, whether it’s the undrinkable 1787 Lafite or the eminently drinkable 1945 Mouton, and what makes them command such astronomic prices, is their scarcity value.

The world seems to have an ever-increasing appetite for collecting unusual old things, be they baseball cards, 1950s Formica furniture or steam train memorabilia, and it’s only natural that rare wines are subject to this same collecting mania.

Now, with more and more people discovering the pleasures of drinking wine, especially the newly rich of China and East Asia, the prices of all fine wines will continue to rise and it will only be a matter of time before Mr. Jefferson’s bottle, and several others on our list, see their formally eye-popping prices surpassed as ever richer and ever more determined collectors compete for that one, must-have bottle of wine.

www.forbes.com

1. Portrait of Adele Bloch-Bauer by Gustav Klimt ($135,000,000)

This record breaking sale was enabled by a court order by the Austrian government to return the painting to the Artist’s rightful heir. The entire dispute lasted over a year and was necessary to return the painting that was looted by the Nazis during World War II. Skillfully painted in 1907 by the art nouveau master Gustav Klimt, the painting was purchased by Ronald S. Lauder, the cosmetics heir, in 2006.

2. Garçon à la Pipe by Pablo Picasso ($104,100,000)

Created during the Rose Period, Garcon a la Pipe showcases Picasso’s exceptional use of cheerful orange and pink palatte.
The oil on canvas painting, measuring 100 × 81.3 cm (slightly over 39 × 32 inches), displays a Parisian boy holding a pipe in his left hand. The record price auction at the time on May 4, 2004 in Sotheby’s was a bit of a surprise to the core art buyers, because it was painted in the style not usually associated with the pioneering Cubist artist.

3. Dora Maar with Cat by Pablo Picasso ($95,200,000)

Another enormous surprise followed in 2006, when this painting near doubled its inaccurate presale estimate and brought in new record $95,200,000 at auction at Sotheby’s on May 3,2006. Painted in 1941, Picasso’s controversial portrait (one of his last) is sometimes described as an unflattering depiction of his mistress, Dora Maar, who was an artist/photographer and mistress of Picasso whose relationship lasted ten years during the 1930s and 40s.

4. Portrait of Dr. Gachet by Vincent van Gogh ($82,500,000)

This painting by the Dutch Impressionist master Vincent van Gogh suddenly became world-famous when Japanese businessman Ryoei Saito paid $82.5 million for it at auction in Christie’s, New York. Saito was so attached to the painting that he wanted it to be cremated with him when he died. Saito died in 1996 … but the painting was saved. Vincent van Gogh actually painted two versions of Dr Gachet’s portrait. You can view the other version, with a slightly different color scheme, at the Musée d’Orsay in Paris.
5. Bal Au Moulin de la Galette by Pierre-Auguste Renoir ($78,000,000)

Bal au moulin de la Galette, Montmartre was painted by French artist Pierre-Auguste Renoir in 1876. On May 17, 1990, it was sold for $ 78,000,000 at Sotheby’s in New York City to Ryoei Saito, who bought it together with the Portrait of Dr Gachet (see above).

6. Massacre of the Innocents by Peter Paul Rubens ($76,700,000)

This painting by Peter Paul Rubens, painted in 1611, is the only painting in this list which was not painted in the 19th or 20th century. It was sold to Kenneth Thomson, 2nd Baron Thomson of Fleet for $ 76,700,000 at a 2002 Sotheby’s auction.

7. Portrait de l’Artiste sans Barbe by Vincent van Gogh ($71,500,000)

Portrait de l’artiste sans barbe (“Self-portrait without beard”) is one of many self-portraits by Dutch painter Vincent van Gogh. He painted this one in Saint-Rémy-de-Provence, France in September 1889. The painting is a oil painting on canvas and is 40 cm x 31 cm (16″ x 13″). This is an uncommon painting since his other self-portraits show him with a beard. The self-portrait became one of the most expensive paintings of all time when it was sold for $71.5 million in 1998 in New York.

8. Rideau, Cruchon et Compotier by Paul Cézanne ($60,500,000)

This painting by Paul Cézanne, painted in ca. 1893-1894, sold for $60,500,000 at Sotheby’s New York on May 10, 1999 to “The Whitneys”. Whitney, born into one of America’s wealthiest families, was a venture capitalist, publisher, Broadway show and Hollywood film producer, and philanthropist.

9. Femme aux Bras Croisés by Pablo Picasso ($55,000,000)

This work, painted in 1901, was a part of Picasso’s famous Blue Period, a dark, sad time in the artist’s life. The beautiful & various tones of blue are typical. The painting depicts a woman with her arms crossed staring at the endless nothing. Femme aux Bras Croisés was sold for $55,000,000 November 8, 2000, at Christie’s Rockefeller in New York City.

10. Irises by Vincent Van Gogh ($53,900,000)

Vincent van Gogh painted this at Saint Paul-de-Mausole in Saint-Rémy-de-Provence, France in 1889, only one year before his death. In 1987, it became the most expensive painting to date. It was sold for $ 54,000,000 to Alan Bond and later resold to the Getty Museum.

NOTEWORTHY
No. 5, 1948 by Jackson Pollock ($140,000,000?)

Unconfirmed rumors buzzing in the art world now place this painting at the top of the list, at least temporarily. If true, the $140 million price tag would be the highest ever for a painting, besting the $135 million paid for the Gustav Klimt painting Portrait of Adele Block Bauer in June 2006.