Jaguar D-Type $21.7 million

With a highly streamlined body, panels secured with hand-spaced rivets, and the now iconic rear fin, the Jaguar D-Type is as purposeful as it is beautiful. The D-Type was a winning recipe for Jag back in the 1950s, securing wins at Le Mans in three consecutive years.

Their dominating formula included a six-cylinder XK motor with an output of 250bhp that would push on to over 300 km/h thanks to the sleek and highly aerodynamic outer shell.
With such pedigree and limited numbers, it’s no wonder that the 1956 race winner fetched an enormous $21.7 million under the hammer in 2016.

And speaking of notable achievements, this racing sensation went on to pave the way for the legendary E-Type – once described as ‘the most beautiful car in the world’, by a man with real authority on such matters, Enzo Ferrari.

1956 Aston Martin DBR1 $22.5 million

This gorgeous 1956 Aston Martin DBR1 is a marvel of British post-war engineering. Its elongated nose plays home to a 2.5-litre straight-six race motor, which is flanked by long, sweeping lines to its pinched rear tail. It truly is a remarkable thing to behold.

Only five of these race-derived DBR1s were ever produced, and this particular car went on to sell for over $22.5 million. And it’s no wonder when you take a look at its unique pedigree, with an amazing history of previous pilots, including Roy Salvadori, Jack Brabham and Carroll Shelby. And in case that wasn’t enough, this incredible car went on to win the 1959 Nürburgring 1,000km under the fearless handling of none other than Sir Stirling Moss.

1964 Ferrari 275 GTB/C Speciale $26.4 million

Aside from being an exquisitely striking motorcar, this 275 GTB/C Speciale is also extremely rare in its own right – even more so than its coveted stablemate and predecessor, the 250 GTO. Based on the road-going 275 GTB, there were only three ‘competizione’ or competition chassis ever build by Ferrari, with those three cars made specifically for FIA homologation and racing.

The three cars in full competizione spec, including this one sold at auction in 2014, boasted a significant 70bhp increase in power over their road-based siblings, as well as substantial weight saving measures. That, in combination with a 320bhp V12 with six mounted Weber carburettors and a long, documented history meant that in Monterey back in 2014, this immensely desirable Italian classic sold for a huge $26.4 million – almost a comparative bargain when considering some other ‘60s Italian icons that feature further down this epic list.

1967 Ferrari 275 GTB/4*S N.A.R.T. Spider $27.5 million

1967 is a particularly fine vintage if you’re in the market for a red Italian barchetta. One of only 10 N.A.R.T. Spiders to ever come into existence over a single year of production, this long-nosed Italian roadster is always in high demand. Sporting a 300bhp 3.2-litre V12 motor, this Spider has certainly got a sting, even by modern standards. On the exterior, there are many classic 1950s and ’60s design cues to drink in; from delicate spoked chrome wheels to bullet-shaped wing mirrors and smooth lines flowing front to rear.

The elongated acronym in the title, not so fitting for this curvaceous car, stands for North American Racing Team – a group of Le Mans winners amassed by state-side Ferrari distributor and racing driver, Luigi Chinetti.
This rare, single-ownership car went under the hammer in 2013 and fetched a handsome $27.5 million. Film star and racing driver, Steve McQueen, is said to have crashed and totalled his own 275 GTB Spider, and rumour has it he had once set eyes on this particular example.

1956 Ferrari 290 MM $28.05 million

Built to take on the formidable World Sportscar Championship in the mid 1950s, the Ferrari 290 MM was developed specially for the 1956 season. Beneath the sleek outer shell, featuring the signature single nacelle hump, sits a potent front-mounted 320bhp V12, mated to a keen four-speed transmission.

As its initials may suggest, the 290 MM was set to take on the challenge of the mighty Mille Miglia – an infamous open-road endurance race. With chassis number 0626, the car in question was piloted up those meandering mountain passes by Juan Manuel Fangio in 1956. Of the 426 cars that entered the race, 365 would start, but only 182 would finish. Fangio fought his way up the rankings and placed an impressive fourth overall.

The unique racing history behind this car, not to mention its staggering beauty, meant that its final sale price tipped in at an impressive $28.05 million.
And if you were after proof of Ferrari’s timeless designs, there are many small details introduced in the original 290s that have made it through to Ferrari’s latest attempts at a single-seat speedster, with the acclaimed Monza SP1.

1954 Mercedes-Benz W196 R $29.6 million

A true triumph of engineering, the W196 R ‘Monoposto’ may be the least instantly recognisable yet ultimately historically significant car to make this outstanding list.

Developed for the 1954 season of the Grand Prix under the new rules and increasingly rigorous regulations, the W196 R was lighter, stiffer and faster than anything Mercedes-Benz had ever entered into the competitive arena. Its new in-line eight-cylinder engine was able to push 256bhp to the rear wheels at a spine-tingling 8,260rpm. This silver bullet would then see legendary F1 wheelman, Juan Manuel Fangio, secure his second world championship in the car’s debut year.

At the time of sale, back in 2013, this streamlined Formula 1 championship calibre car broke records. The final price as the hammer fell, an eye-watering $29.6 million, was the then most expensive car to ever sell at auction. And it remains to this day the sole representation of a W196 R in private ownership.

1957 Ferrari 335 Sport Scaglietti $35.7 million

With a wonderfully curvaceous shape, fluid lines and exposed side-mounted exhausts, this stunning Ferrari 335S has an incredible racing profile, seeing action at the Sebring 12 Hours in the late ‘50s, to the Mille Miglia and 24 Hours of Le Mans.

At the time of sale back in 2016, the $35.7 million final bid made this motorcar a record breaker in its own right – marking it as the most expensive race car ever sold at auction.

Weighing only 880kg and packing a serious punch from its 4-litre V12, the 335 Sport Scaglietti would regularly reach over 300 km/h on a long straight. The 335S was Ferrari’s answer to the powerful Maserati 450S – a close rival that was regularly outmanoeuvring and outgunning the 290 MM on track at the time. Only four of these amazing Italian front-engine ‘50s racers were ever made, making them a very rare and highly sought-after commodity. And frankly it’s not hard to see why. The 335S is an icon and represents true motoring nirvana.

1962 Ferrari 250 GTO $48.4 million

In pole position comes the coveted Ferrari 250 GTO. In fact, two stellar examples, both with chassis numbers dating back to 1962, occupy the first and second most expensive cars ever sold at auction.
The more affordable of the two tipped the scales at just over $38.1 million, with the true record holder breaking boundaries at an astonishing $48.4 million.

With only 36 250 GTOs to ever leave the factory over just a two-year production span, it’s no surprise the legendary Italian marque continues to generate such interest and fetch incredible premiums. Designed under the steadfast efforts of Giotto Bizzarrini and Sergio Scaglietti, the 250 GTO is powered by an intoxicating 3-litre V12. Its main historic rivals were also notable power punchers, like the Shelby Cobra and Jaguar E-Type, but with many examples boasting superior race pedigree, there’s certainly no argument that the GTO utterly deserves the pinnacle on which it stands.

It has even been suggested that in a private sale that took place in 2018, a Tour de France-winning GTO sold for a staggering $70 million, making it the most expensive car in the world and part of a very exclusive club indeed.