Gentlemen, release your tannins. While many on the sunny coast of California enjoy their two-buck-Chuck, other wine connoisseurs and collectors seek out a more expensive taste. These five bottles came at a hefty price tag, but hold a rich history and one of them befell a terrible tragedy.

#5 – Chateau Margaux 1787 – $225,000

At nearly a quarter of a million dollars, this wine had to be something special, and it was. It came from the personal wine cellar of none other than Thomas Jefferson. The eighteenth century wine was meant for a beautiful dinner at the Four Seasons, but met it’s tragic end when a waiter dropped the bottle, causing it to shatter on the floor. The insurance company covered the cost, but the bottle and the wine were never truly enjoyed.

#4 – Chateau Lafite’s 1869 – $230,000

In a heated auction in Hong Kong, this rare vintage brought in a hefty sum three times over. The winner of this prized 19th century bottle purchased all three available for a grand total of $690,000. All three bottles were of standard size and are thus the most expensive standard-sized bottles in history.

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#3 – 1907 Heidsieck – $275,000

While over 2,000 bottles of this 1907 champagne were sold at auctions world-wide, the most one bottle brought in was $275,000. Its history is worth the price, some say, because it came from the bottom of the ocean off of a Swedish Freighter bound for royalty in Russia, but cut short on its journey by a torpedo from a German U-boat submarine. The bottles were recovered as part of an excavation in 1998.

#2 – 1947 Cheval-Blanc – $304,375

To the average joe, you may see a year and wonder how a bottle could be so expensive. After all, in the grand scheme of things, 1947 wasn’t that long ago. However, the thing a wine connoisseur may know that you don’t is that this wine came from Saint-Emilion and had a Class A status. The grapes grown between April and October of 1947 were said to be legendary and this is the only bottle left to have that flavor captured. It is said that of all the merlot available, this is one of only two ever awarded a Class A status.

#1 – Screaming Eagle Cabernet Sauvignon 1992 – $500,000

Said to be the best thing to ever come out of the great Napa Valley, this wine was only made available in 1995 for a short period and it was drank almost entirely, except for this bottle. Still, how much can wine perfection truly cost? Well, for one anonymous buyer, there is no price cap for charity, as this was his winning bid at a charity auction. Did he think the wine was worth the full half million or did he just want to give to a good cause? We may never know, but we are able to say that a price tag of $500,000 tops the list as the most expensive bottle ever sold.