You could buy 2917 Polo Vivos for the price this 250 GTO sold for in 2014.

Expensive cars. Always a hot topic. But we’re not talking about modern exotics here, because nothing built in the last decade can hold a candle to the most valuable machinery ever sold.

A McLaren P1 LM, which was the priciest of all new cars when the last of six sold for around $3.7-million (R49.2-million) earlier this year, wouldn’t even rank in the top 100 most expensive cars of all time. 

Like comic books, baseball cards, coins and fine wine, some cars appreciate with age, and out of the top five most expensive listed below, the youngest is 53-years old. 

You might also notice a trend here: Not only are four of the five vehicles Ferraris, four are historic race cars proving that motorsport provenance, especially that of the Italian variety, boosts value. 

We must also add an asterisk to this list as only vehicles sold at auction, where selling prices are made public, qualify. It’s quite possible some Arabian Sheikh has spent much, much more on a solitary piece of precious metal for his private collection, but we’ll never know because the cash exchanged hands behind closed doors.

1. 1962 Ferrari 250 GTO

Price: $38 115 000 (R507-million)

Ferrari dominated GT racing between 1962 and 1964 with its V12-powered 250 GTO Berlinetta, and this particular example was driven by famed Frenchman Jo Schlesser among others. It was the 19th of only 39 units made, and has changed hands only five times in its life. The previous owner held it for 49 years, and the other three raced it in the '60s. 

Though this example’s racing history was relatively lacklustre, and was crashed numerous times (including one incident which took the life of Henri Orellier), it smashed the previous record for the most expensive car when it sold at an American auction in 2014. It was expected, however, to sell for up to $70-million at the time.

2. 1957 Ferrari 335 Sport

$35 673 848 (R474-million)

When this car crossed a French auction block last year it became the most expensive car sold in Europe. Only four were made between 1957 and ‘58, and this one was driven to victory by Stirling Moss at the 1958 Cuban Grand Prix.

Its 4-litre V12 made just under 300kW (stratospheric at the time) and pushed it to a top speed of around 300km/h down the Le Mans Mulsanne straight. Although unconfirmed, it’s believed this car’s new owner is Barcelona soccer star Lionel Messi.

3. 1954 Mercedes-Benz W196R

$29 700 000 (R395-million)

It’s unclear exactly how many W196 racers were made, but we do know that this example, which raced to wins at the 1954 German and Swiss Grands Prix by five-time world champion Juan Fangio, is the only one not currently owned by Mercedes itself or in the hands of an institutional museum. 

At the time of its sale in 2013 it was the most expensive car ever sold at auction, and was notable for its unrestored “fresh-from-the-track” condition.

4. 1956 Ferrari 290 MM

$28 050 000 (R373-million)

Though Fangio indeed drove this car at the 1956 Mille Miglia (an Italian endurance race it was named for), he only managed fourth place. Still, with that name attached to its pedigree, this 290 MM managed to slot itself into the top five most expensive cars when it sold at a US auction in 2015. 

Fangio may have failed to score a win with this particular car, but American ace Masten Gregory and Italian Luigi Musso won the Buenos Aires 1000km in it in 1957.

5. 1967 Ferrari 275 GTB/4 N.A.R.T. Spider

$27 500 000 (R366-million)

American mail-order businessman Eddie Smith bought this car new in 1967, making it the only genuine "one owner" car in this list when it sold in 2013. During its life Smith resisted sales to Steve McQueen, Ralph Lauren and racing driver Phil Hill, but after his death in 2007 his son opted to give it a new home rather than keep it stored behind lock and key as it had been for the past six years. 

The N.A.R.T. (which stands for North American Racing Team) was regularly driven while Eddie Sr was alive, and Eddie Jr donated some of the sale's proceeds to charity. Only 10 N.A.R.T Spiders were made.

IOL Motoring