The 5 Most Expensive Cars of All Time

Like rare works of art, classic cars can be a great long-term investment -- if you have more money than you know what to do with.

Mar 2, 2014 at 3:00PM

Even the least materialistic among us can appreciate the aesthetics of a well-built car. We certainly spend a lot of time with our cars -- the average commuter spends about 38 hours a year just sitting in traffic, and the average daily commute to and from work is a bit less than an hour. But most of us don't get into exquisitely tuned high-performance supercars to head to the office, which makes the sight of these machines a source of excitement, envy, and wonder.

The typical supercar costs hundreds of thousands of dollars to own and maintain, putting it well beyond reach for most people. But some cars leave the brand-new Lambos, Ferrarris, Bentleys, and Bugattis you might see in the dust -- not in terms of raw power, but in costs. The five one-of-a-kind cars I'll look at here, as ranked by Bloomberg and other sources, set sale records that may not be matched for a long time. The classic-car market has made them its best works of art, but you might think otherwise, so read on to find out what makes them the pinnacle of performance and the peak of prestige.

Bugatti
Source: Wikimedia Commons.

5th: 1931 Bugatti Royale Type 41 Kellner Coupe -- $20.2 million
This beautiful example of pre-war ultra-luxury was one of only six ever built (the preceding car, now owned by Bugatti parent Volkswagen, has a slightly different paint job than the actual sale model), and was initially the victim of very bad timing. Ettore Bugatti wanted to sell these cars to royalty, but by building during the depths of the Great Depression, he wound up pricing himself out of even the richest markets as people all tightened their belts at the same time. When it went up for sale again in 2002, London's Telegraph called it "[t]he grandest of all luxury cars ... so pompous and arrogant in concept that not even the aristocrats at whom it was aimed in the late Twenties had the front -- or perhaps the money -- to buy one at twice the price of a Rolls-Royce." The car remains one of the largest ever built, and its 12.7-liter engine was so powerful that it was repurposed (in blocks of two or four) to drive railcars that once set world speed records of 122 miles per hour.

Ferrari
Source: Wikimedia Commons.

4th: 1967 Ferrari 275 GTB/4 NART Spider  -- $27.5 million
This car turned heads last August, when it was sold to former Tommy Hilfiger honcho Lawrence Stroll for about $10 million more than expected. There were only 10 ever built, and the model's pedigree includes an appearance in the 1968 version of The Thomas Crown Affair and ownership by Steve McQueen (one of the film's headliners), who crashed his car and later tried to buy the model that went up for auction without success. The car sold had only one owner, who would have paid roughly $15,000 for it when new. That turned out to be a pretty good investment for him, as the car appreciated in value by 17.7% a year over the 46 years of his ownership.

Mbw
Source: Lothar Spurzem via Wikimedia Commons.

3rd: 1954 Mercedes-Benz W196R Formula 1 -- $31.6 million
This was the most expensive car ever sold at auction for several reasons. First, it's the only post-war Mercedes-Benz W196R Silver Arrow in private hands -- only 14 were ever built, 10 of which remain and nine of which are in museum collections. Second, it was a technological marvel for its time, as it was the first fuel-injected F-1 car and boasted advanced aerodynamics, among other breakthroughs. Third, it led legendary Formula 1 driver Juan Manuel Fangio to the 1954 Formula 1 championship -- that's him you see in the car (one of Mercedes' collection) during the 1986 Oldtimer Grand Prix. This car won nine of 12 Grand Prix races it contested with Fangio behind the wheel. Fangio won five Formula 1 championships in his career and is the only driver to win championships with four different teams.

Ferrari
Source: Paolo Fefe via Flickr.

2nd: 1957 Ferrari 250 Testa Rossa -- $40.4 million
This private sale (the car pictured is not the same car, but it is the same model) was nearly twice the old record price for a 250 Testa Rossa, and also became the most expensive car ever sold in Britain, when it was reported by London's Daily Mail a month ago. The model sold (chassis 0704) was originally a prototype designed by Sergio Scaglietti and went on to win 18 endurance races around the world before becoming part of the Henry Ford Museum's collection in 1967. Ferrari historian Marcel Massini calls it "one of the top five Ferraris on the planet," and its price certainly earns it that ranking. This car has never been restored, which is now popular among classic-car collectors as a way to proudly display the vehicle's true history every time it's taken out of the garage.

Ferrari
Source: Wikimedia Commons.

1st: 1963 Ferrari 250 GTO  -- $52 million
This particular Ferrari (or at least its model, as the preceding photo does not show the car sold) has been a controversial subject in Ferrari-aficionado circles. It's been called the "Greatest Ferrari of All Time" by Motor Trend Classic and was nominated as the top sports car of all time by Sports Car International. It is essentially the Mona Lisa of classic cars and has been setting records at auction for almost three decades -- a 250 GTO seized from a drug lord in 1984 sold at auction in 1987 for $1.6 million, and prices have generally been going straight up ever since.

This sale, which took place last October, remains the high-water mark for classic car sales in spite of fervent competition. There were only 36 of these 300-horsepower V-12-engined cars produced, and this particular sale (chassis number 5111GT) won the 1963 Tour de France and won its class at the 1963 Coupes du Salon, continuing to race GT events at a high level until a sale in 1965. Like the second-most-valuable car on the list, this Ferrari was also a private sale confirmed by third parties.

However, the rapid rise in sale prices is also stoking fears of a bubble. Ferrari dealer Joe Macari told Bloomberg:

It's a cult car. ... If you're a billionaire, you feel you have to have one. I don't understand the appeal of them. They're not very beautiful and they never won Le Mans. I'd rather have a Testa Rossa.

Historic Auto Group founder Dietrich Hatlapa also pointed out:

Price rises of 55% [the last major 250 GTO sale took place last year at a price 49% below this sale] aren't sustainable in any market. We're not saying the market is going to collapse. It will probably average out over time.

Rare classic Ferraris have increased in value by roughly 15% a year for decades, so the buyer of this car is likely to turn a profit -- eventually.

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